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Mini-Reviews in Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 1389-5575
ISSN (Online): 1875-5607

Review Article

A Review Exploring Therapeutic Worth of 1,3,4-Oxadiazole Tailored Compounds

Author(s): Garima Verma, Mohemmed F. Khan, Wasim Akhtar, Mohammad Mumtaz Alam, Mymoona Akhter and Mohammad Shaquiquzzaman*

Volume 19, Issue 6, 2019

Page: [477 - 509] Pages: 33

DOI: 10.2174/1389557518666181015152433

Price: $65

Abstract

1,3,4-Oxadiazole, a five-membered aromatic ring can be seen in a number of synthetic molecules. The peculiar structural feature of 1,3,4-oxadiazole ring with pyridine type of nitrogen atom is beneficial for 1,3,4-oxadiazole derivatives to have effective binding with different enzymes and receptors in biological systems through numerous weak interactions, thereby eliciting an array of bioactivities. Research in the area of development of 1,3,4-oxadiazole-based derivatives has become an interesting topic for the scientists. A number of 1,3,4-oxadiazole based compounds with high therapeutic potency are being extensively used for the treatment of different ailments, contributing to enormous development value. This work provides a systematic and comprehensive review highlighting current developments of 1,3,4-oxadiazole based compounds in the entire range of medicinal chemistry such as anticancer, antifungal, antibacterial, antitubercular, anti-inflammatory, antineuropathic, antihypertensive, antihistaminic, antiparasitic, antiobesity, antiviral, and other medicinal agents. It is believed that this review will be of great help for new thoughts in the pursuit for rational designs for the development of more active and less toxic 1,3,4-oxadiazole based medicinal agents.

Keywords: 1, 3, 4-Oxadiazole, therapeutic worth, anticancer, antimicrobial, antioxidant, isoforms.

Graphical Abstract

[1]
Dua, R.; Shrivastava, S.; Sonwane, S.K.; Srivastava, S.K. Pharmacological significance of synthetic heterocycles scaffold. Adv. Biol. Res., 2011, 5(3), 120-144.
[2]
Hote, S.V.; Bhoyar, S.P. Heterocyclic compound- A review. IOSR J. Applied Chem., 2014, 2014, 43-46.
[3]
Martins, P.; Jesus, J.; Santos, S.; Raposo, L.R.; Rodrigues, C.R.; Baptista, P.V.; Fernandes, A.R. Heterocyclic anticancer compounds: recent advances and paradigm shift towards the use of nanomedicine’s tool box. Molecules, 2015, 20(9), 16852-16891.
[4]
Shaikh, A.A.; Raghuwanshi, M.G.; Molvi, K.I.; Nazim, S.; Ahmed, A. Schiff’s bases and amides of selected five membered heterocyclic compounds: a review. J. Chem. Pharm. Res., 2013, 5(6), 14-25.
[5]
Saini, M.S.; Kumar, A.; Dwivedi, J.; Singh, R. A review: biological significance of heterocyclic compounds. Int. J. Pharm. Sci. Res., 2013, 4(3), 66-77.
[6]
Dar, A.M. Shamsuzzaman. A concise review on the synthesis of pyrazole heterocycles. J. Nucl. Med. Radiat. Ther., 2015, 6(5), 1-5.
[7]
T.P. Selvam; C.R. James; P.V. Dniandev; S.K. Valzita. A minireview of pyimidine and fused pyrimidine marketed drugs. Res. Pharm., 2012, 2(4), 1-9.
[8]
Bostrom, J.; Hogner, A.; Llinas, A.; Wellner, E.; Plowright, A.T. Oxadiazoles in medicinal chemistry. J. Med. Chem., 2012, 55(5), 1817-1830.
[9]
Kavitha, S.; Gnanavel, S.; Kannan, K. Biological aspects of 1,3,4,-oxadiazole. Asian J. Pharm. Clin. Res., 2014, 7, 11-20.
[10]
Kumar, K.A.; Jayaroopa, P.; Kumar, G.V. Comprehensive review on the chemistry of 13,4-oxadiazoles and their applications. Int. J. Chemtech Res., 2012, 7(4), 1782-1791.
[11]
Sharma, S.; Sharma, P.K.; Kumar, N.; Dudhe, R. A review: oxadiazole their chemistry and pharmacological potentials. Der. Pharma Chem., 2010, 2(4), 253-263.
[12]
Oliveira, C.S.D.; Lira, B.F.; Filho, J.M.B.; Lorenzo, J.G.F.; Filho, P.F.D.A. Synthetic approaches and pharmacological activity of 1,3,4-oxadiazoles: A review of the literature from 2000-2012. Molecules, 2012, 17(9), 10192-10231.
[13]
Khaliullah, H.; Ahsan, M.J.; Hedaitullah, M.; Khan, S.; Ahmed, M. 1,3,4-oxadiazole: A biologically active scaffold. Mini Rev. Med. Chem., 2012, 12(8), 789-801.
[14]
Sun, J.; Makawana, J.A.; Zhu, H.L. 1,3,4-oxadiazole derivatives a potential biological agent. Mini Rev. Med. Chem., 2013, 13(12), 1725-1743.
[15]
Bhatia, S.; Gupta, M. 1,3,4-oxadiazole as antimicrobial agents: An overview. J. Chem. Pharm. Res., 2011, 3(3), 137-147.
[16]
Zarghi, A.; Tabatabai, S.A.; Faizi, M.; Ahadian, A.; Navabi, P.; Znaganeh, V.; Shafiee, A. Synthesis and anticonvulsant activity of new 2-substituted-5-(2-benzyloxyphenyl)-1,3,4-oxadiazoles. Bioorg. Med. Chem. Lett., 2005, 15(7), 1863-1865.
[17]
Jin, L.; Chen, J.; Song, B.; Chen, Z.; Yang, S.; Li, Q.; Hu, D.; Xu, R. Synthesis, structure and bioactivity of N’-substituted benzylidene-3,4,5-trimethoxybenzohydrazide and 3-acetyl-2-substituted phenyl-5-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1,3,4-oxadizole derivatives. Bioorg. Med. Chem. Lett., 2006, 16(19), 5036-5040.
[18]
El-Emam, A.A.; Al-Deeb, O.A.; Al-Omar, M.; Lehmann, J. Synthesis, antimicrobial, and anti-HIV-1 activity of certain 5-(1-adamanntyl)-2-substituted thio-1,3,4-oxadiazoles and 5-(1-adam-antyl)-3-substituted aminomethyl-1,3,4-oxadiazoline-2-thiones. Bioorg. Med. Chem., 2004, 12, 5107-5113.
[19]
Blakney, A.K.; Jiang, Y.; Whittington, D.; Woodrow, K.A. Simultaneous measurement of etravirine, maraviroc and raltegravir in pigtail macque plasma, vaginal secretions and vaginal tissue using a LC-MS/MS assay. J. Chrom. B., 2016, 1025, 110-118.
[20]
Gnanasekaran, K.K.; Nammalwar, B.; Murie, M.; Bunce, R.A. Efficient synthesis of 1,3,4-oxadiazoles promoted by NH4Cl. Tetrahedron Lett., 2014, 55(50), 6776-6778.
[21]
Kumar, R.; Khokara, S.L. Chemistry and common synthetic route of 1,3,4-oxadiazole: an important heterocyclic moiety in medicinal chemistry. Intl. J. Pharm. Life Sci., 2012, 2(5), 126-143.
[22]
Mico, B.A.; Baughman, R.A.; Benet, L.Z. Determination of tiodazosin in plasma in whole body by high-performance liquid chromatography. J. Chrom., 1982, 230, 203-206.
[23]
Lenz, E.M.; Kenyon, A.; Martin, S.; Temesi, D.; Jones, J.C.; Tomkinson, H. The metabolism of [14C]-zibotentan (ZD4054) in rat, dog and human, the loss of the radiolabel and the identification of an anomalous peak, derived from the animal feed. J. Pharm. Biomed. Anal., 2011, 55(3), 500-517.
[24]
Birch, A.M.; Bowker, S.S.; Butlin, R.J.; Donald, C.S.; Mccoull, W.; Nowak, T.; Plowright, A. Oxadiazole derivatives as dgat inhibitors., 2006. WO 2006064189.
[25]
Coppo, F.T.; Maskell, E.S.L.; Redshaw, S.; Skidmore, J.; Ward, R.W.; Wilson, D.M. 2-Phenyl-5-amino-1,3,4-oxadiazoles and their use as nicotinic acetylcholine receptor ligands. 2007, WO 2007138033 A1.
[26]
Johnstone, C.; Plowright, A. 1,3,4-oxadiazole derivatives as dgat1 inhibitors. 2007, WO 2007138304 A1.
[27]
Barrow, J.C.; Harrison, S.; Mulhearn, J.; Sur, C.; Williams, D.L.; Wolkenberg, S. Novel substituted pyrazoles, 1,2,4-oxadiazoles and 1,3,4-oxadiazoles. 2009, WO 2009146343 A1.
[28]
Birch, A.M. Pal, S.; Pettersen, A.; Tornkinson, G.P. 1,3,4- oxadiazole derivatives and their uses to treat diabetes. 2010, WO 2010070343 A1.
[29]
Asai, A.; Matsuno, K.; Ogo, N.; Takahashi, O.; Masuda, Y.; Muroya, A.; Akiyama, Y.; Ashizawa, T.; Okawara, T. 1,3,4- oxadiazole-2-carboxamide compound. 2013, EP 2520575 A4.
[30]
Sivakumar, M.; Joshi, K.S.; Aware, V.S.; Sarde, A.G.; Bagul, S.M.; Manohar, S.M. Oxadiazole compounds, their preparation and use. 2011, WO 2011104680 A1.
[31]
Gu, Y.G.; He, Y.; Yin, N.; Alexander, D.C.; Cross, J.B.; Metcalf, C.A.; Busch, R. 1,3,4-oxadiazole and 1,3,4-thiadiazole betalactamase inhibitors. 2013, WO 2013149121 A1.
[32]
Sasikumar, P.G.N.; Ramachandra, M.; Naremaddepalli, S.S.S. 1,3,4-oxadiazole and 1,3,4-thiadiazole derivatives as immunomodulators. 2015, WO 2015033301 A1.
[33]
DeMarshall, C.A.; Nagele, E.P.; Sarkar, A.; Acharya, N.K.; Godsey, G.; Goldwaser, E.L.; Kosciuk, M.; Thayasivam, U.; Han, M.; Belinka, B.; Nagele, R.G. Detection of Alzheimer’s disease at mild cognitive impairment and disease progression using autoantibodies as blood-based biomarkers. Alz. Dement. Diagn. Assessment Dis. Monitor, 2016, 3, 51-62.
[34]
Zhang, C.; Du, Q.Y.; Chen, L.D.; Wu, W.H.; Liao, S.Y.; Yu, L.H.; Liang, X.T. Design, Synthesis and evaluation of novel tacrine-multialkoxybenzene hybrids as multi-targeted compounds against Alzheimer’s disease. Eur. J. Med. Chem., 2016, 116, 200-209.
[35]
Kumar, J.; Meena, P.; Singh, A.; Jameel, E.; Maqbool, M.; Mobashir, M.; Shandilya, A.; Tiwari, M.; Hoda, N.; Jayaram, B. Synthesis and screening of triazolopyrimidine scaffold as multi-functional agents for Alzheimer’s disease therapies. Eur. J. Med. Chem., 2016, 119, 260-277.
[36]
Onishi, T.; Iwashita, H.; Uno, Y.; Kunitomo, J.; Saitoh, M.; Kimura, E.; Fujita, H.; Uchiyama, N.; Kori, M.; Takizawa, M. A novel glycogen synthase kinase-3- inhibitor 2-methyl-5-(3-4-[(S)-methylsulfinyl]phenyl-1-benzofuran-5-yl)-1,3,4-oxadiazole decreases tau phosphorylation and ameliorates cognitive deficits in a transgenic model of Alzheimer’s disease. J. Neurochem., 2011, 119(6), 1330-1340.
[37]
Abdelazeem, A.H.; Khan, S.I.; White, S.W.; Sufka, K.J.; McCurdy, C.R. Design, synthesis and biological evaluation of bivalent benzoxazolone and benzothiazolone ligands as potential anti-inflammatory/analgesic agents. Bioorg. Med. Chem., 2015, 23(13), 3248-3259.
[38]
Sarigol, D.; Uzgoren-Baran, A.; Tel, B.C.; Somuncuoglu, E.I.; Kazkayasi, I.; Ozadali-Sari, K.; Okay, G.; Ertan, M.; Tozkoparan, B. Novel thiazolo[3,2-b]-1,2,4-triazoles derived from naproxen with analgesic/anti-inflammatory properties: synthesis, biological evaluation and molecular modeling studies. Bioorg. Med. Chem., 2015, 23(10), 2518-2528.
[39]
Viveka, S. Dinesha; Shama, P.; Nagarja, G.K.; Ballav, S.; Kerker, S. Design and synthesis of some new pyrazolyl-pyrazolines as potential anti-inflammatory, analgesic and antibacterial agents. Eur. J. Med. Chem., 2015, 101, 442-451.
[40]
Biju, C.R.; Ilango, K.; Prathap, M.; Rekha, K. Design and microwave-assisted synthesis of 1,3,4-oxadiazole derivatives for analgesic and anti-inflammatory activity. J. Young Pharm., 2012, 4(1), 33-37.
[41]
Ragahavendra, R.; Mahadevan, K.M.; Satyanarayan, N.D.; Bhanuprakash, V.; Venkatesan, G.; Yogisharadhya, R. Analgesic, antibacterial and antiviral activities of 2-(5-Alkyl-1,3,4-oxadiazol-2-yl)-3H-benzo[f]chromen-3-ones. Indian J. Pharm. Sci., 2012, 74(4), 367-371.
[42]
Singh, A.K.; Lohani, M.; Parhtasarthy, R. Synthesis, characterization and anti-inflammatory activity of some 1,3,4 -oxadiazole derivatives. Iran. J. Pharm. Res., 2013, 12, 319-323.
[43]
Koksal, M.; Yarim, M.; Erdal, A.; Bozkurt, A. Synthesis and anti-inflammatory activities of novel 5-(3,4-dichlorophenyl)-3-[(4-substitutedpiperazin-1-yl)methyl]-1,3,4-oxadiaxole-2(3H)-thiones. Drug Res., 2014, 64(2), 66-72.
[44]
Bansal, S.; Bala, M.; Suthar, S.K.; Choudhary, S.; Bhattacharya, S.; Bhardwaj, V.; Singla, S.; Joseph, A. Design and synthesis of novel 2-phenyl-5-(1,3-diphenyl-1H-pyrazol-4-yl)-1,3,4-oxadiazoles as selective COX-2 inhibitors with potent anti-inflammatory activity. Eur. J. Med. Chem., 2014, 80, 167-174.
[45]
Palkar, M.B.; Singhai, A.S.; Ronad, P.M.; Vishwanathswamy, A.H.M.; Boreddy, T.S.; Veerapur, V.P.; Shaikh, M.S.; Rane, R.A.; Kapoormath, R. Synthesis, pharmacological screening and in silico studies of new clas of diclofenac analogues as promising anti-inflammatory agents. Bioorg. Med. Chem., 2014, 22(10), 2855-2866.
[46]
Rathore, A.; Rahman, M.U.; Siddiqui, A.A.; Ali, A.; Shaharyar, M. Design and synthesis of benzimidazole analogs endowed with oxadiazole as selective COX-2 inhibitor. Arch. Pharm. Chem. Life Sci., 2014, 347(12), 923-935.
[47]
Banerjee, A.G.; Das, N.; Shengule, S.A.; Srivastava, R.S.; Shrivastava, S.K. Synthesis, characterization, evaluation and molecular dynamics studies of 5,6-diphenyl-1,2,4-triazin-3(2H)-one derivatives bearing 5-substituted 1,3,4-oxadiazole as potential anti-inflammatory and analgesic agents. Eur. J. Med. Chem., 2015, 101, 81-95.
[48]
Abd-Ellah, H.S.; Aziz, M.A.; Shoman, M.E.; Beshr, E.A.M.; Kaoud, T.S.; Ahmed, A.S.F.F. Novel 1,3,4-oxadiazole/oxime hybrids: Synthesis, docking studies and investigation of anti-inflammatory, ulcerogenic liability and analgesic activities. Bioorg. Chem., 2016, 69, 48-63.
[49]
Toma, A.; Hapau, D.; Vlase, L.; Mogosan, C.; Zaharia, V. Synthesis and anti-inflammatory activity of 5-(pyridin-4-yl)-1,3,4-oxadiazole-2-thiol, 5-(pyridin-4-yl)-1,3,4-thiadiazole-2-thiol and 5-(pyridine-4-yl)-1,2,4-triazole-3-thiol derivatives. Clujul Med., 2013, 86(1), S34-S39.
[50]
Ingale, N.; Maddi, V.; Plakar, M.; Ronad, P.; Mamledesai, S.; Vishwanathswamy, A.H.M.; Satyanarayana, D. Synthesis and evaluation of anti-inflammatory and analgesic activity of 3-[(5-substituted-1,3,4-oxadiazol-2-yl-thio)acetyl]-2H-chromen-2-ones. Med. Chem. Res., 2012, 21(1), 16-26.
[51]
Amir, M.; Saifulah, K.; Akhter, W. Design, synthesis and pharmacological evaluation of 1,3,4-oxadiazole derivatives of aryl acetic acid as anti-inflammatory and analgesic agents. Indian J. Chem., 2011, 50B(08), 1107-1111.
[52]
Sahoo, U.; Seth, A.K.; Balaraman, R. Design, synthesis of some novel 1,3,4-oxadiazole derivatives bearing benzimidazole nucleus and biological evaluation of their possible in vitro anti-inflammatory and antioxidant activity. Int. J. Chemtech Res., 2014, 6(4), 2427-2437.
[53]
Almasirad, A.; Mousavi, Z.; Tajik, M.; Assarzadeh, M.J.; Shafiee, A. Synthesis, analgesic and anti-inflammatory activities of new methyl-imidazolyl-1,3,4-oxadiazoles and 1,2,4-triazoles. Daru J. Pharm. Sci., 2014, 22(1), 1-8.
[54]
Almasirad, A.; Shafiee, A.; Abdollahi, M.; Noeparast, A.; Shahrokhinejad, N.; Vousooghi, N.; Tabatabai, S.A.; Khorasani, R. Synthesis and analgesic activity of new 1,3,4-oxadiazoles and 1,2,4-triazoles. Med. Chem. Res., 2011, 20(4), 435-442.
[55]
80. Nimavat, B.; Mohan, S.; Saravanan, J.; Deka, S.; Talukdar, A.; Sahariah, B.J.; Dey, B.K.; Sarma, R.K. Synthesis and characterization of some novel oxadiazoles for in vitro anti-inflammatory activity. Int. J. Res. Pharm. Chem., 2012, 2(3), 594-602.
[56]
Kumar, V.; Sharma, S.; Husain, A. Synthesis and in vivo anti-inflammatory and analgesic activities of oxadiazoles clubbed with benzothiazole nucleus. Int. Curr. Pharm. J., 2015, 4(12), 457-461.
[57]
Rathore, A.; Sudhakar, R.; Ahsan, M.J.; Ali, A.; Subbarao, N.; Jadav, S.S.; Umar, S.; Yar, M.S. In vivo anti-inflammatory activity and docking study of newly synthesized benzimidazole derivatives bearing oxadiazole and morpholine rings. Bioorg. Chem., 2016, 70, 107-117.
[58]
Wu, P.P.; Zhang, K.; Lu, Y.J.; He, P.; Zhao, S.Q. In vitro and in vivo evaluation of antidiabetic activity of ursolic acid derivatives. Eur. J. Med. Chem., 2014, 80, 502-508.
[59]
Lakshminarayana, N.; Prasad, Y.R.; Gharat, L.; Thomas, A.; Narayanan, S.; Raghuram, A.; Srinivasan, C.V.; Gopalan, B. Synthesis and evaluation of some novel dibenzo[b,d]furan carboxylic acids as potential anti-diabetic agents. Eur. J. Med. Chem., 2015, 45, 3709-3718.
[60]
Sharma, R.; Sonam, S.S. Design and synthesis of sulfonamide derivatives as pyrrolidine and piperidine as anti-diabetic agents. Eur. J. Med. Chem., 2015, 90, 342-350.
[61]
Taha, M.; Ismail, N.H.; Imran, S.; Rokei, M.Q.B.; Saad, S.M.; Khan, K.M. Synthesis of new oxadiazole derivatives as α-glucosidase inhibitors. Bioorg. Med. Chem., 2015, 23(15), 4155-4162.
[62]
Nazreen, S.; Alam, M.S.; Hamid, H.; Yar, M.S.; Shafi, S.; Dhulap, A.; Alam, P.; Pasha, M.A.Q.; Bano, S.; Alam, M.M.; Haider, S.; Ali, Y.; Kharbanda, C.; Pillai, K.K. Design, synthesis, in silico molecular docking and biological evaluation of novel oxadiazole based thiazolidine-2,4-diones bis-heterocycles as PPAR-ɣ agonists. Eur. J. Med. Chem., 2014, 87, 175-185.
[63]
Kashtoh, H.; Hussain, S.; Khan, A.; Saad, S.M.; Khan, J.A.J.; Khan, K.M.; Perveen, S.; Choudhary, M.I. Oxadiazoles and thiadiazoles: Novel α-glucosidase inhibitors. Bioorg. Med. Chem., 2014, 22(19), 5454-5465.
[64]
Taha, M.; Ismail, N.H.; Imran, S.; Rokei, M.Q.B.; Saad, S.M.; Khan, K.M. Synthesis of new oxadiazole derivatives as α-glucosidase inhibitors. Bioorg. Med. Chem., 2015, 23(15), 4155-4162.
[65]
Toth, S.; Szocs, B.; Kaszas, T.; Docsa, T.; Gergely, P.; Somsak, L. Synthesis of 2-(β-D-glucopyranosylamino)-5-substituted-1,3,4-oxadiazoles for inhibition of glycogen phosphorylase. Carbohydr. Res., 2013, 381, 196-204.
[66]
Nakano, H.; Inoue, T.; Kawasaki, N.; Miyataka, H.; Matsumoto, H.; Taguchi, T.; Inagaki, N.; Nagai, H.; Satoh, T. Synthesis and biological activities of novel antiallergic agents with 5-lipoxygenase inhibiting action. Bioorg. Med. Chem., 2000, 8(2), 373-380.
[67]
Su, W.; Wan, Q.; Huang, J.; Han, L.; Chen, X.; Chen, G.; Olsen, N.; Zheng, S.G.; Liang, D. Culture medium from TNF-α–stimulated mesenchymal stem cells attenuates allergic conjunctivitis through multiple antiallergic mechanisms. J. Allergy Clin. Immunol., 2015, 136(2), 423-432.
[68]
Guda, D.R.; Park, S.J.; Lee, M.W.; Kim, T.J.; Lee, M.E. Syntheses and anti-allergic activity of 2-((bis(trimethylsilyl)methylthio/methylsulfonyl)methyl)-5-aryl-1,3,4-oxadiazoles. Eur. J. Med. Chem., 2013, 62, 84-88.
[69]
Reddy, G.D.; Park, S.J.; Cho, H.M.; Kim, T.J.; Lee, M.E. Antiallergic activity profile in vitro RBL-2H3 and in vivo passive cutaneous anaphylaxis mouse model of new sila-substituted 1,3,4- oxadiazoles. J. Med. Chem., 2012, 55(14), 6438-6444.
[70]
Mao, Z.W.; Zheng, X.; Lin, Y.P.; Hu, C.Y.; Wang, X.L.; Wan, C.P.; Rao, G.X. Design, synthesis and anticancer activity of novel hybrid compounds between benzofuran and N-aryl piperazine. Bioorg. Med. Chem. Lett., 2016, 26(15), 3421-3424.
[71]
Turan-Zitouni, G.; Altintop, M.D.; Ozdemir, A.; Kaplancikli, Z.A.; Ciftci, G.A.; Temel, H.E. Synthesis and evaluation of bis-thiazole derivatives as new anticancer agents. Eur. J. Med. Chem., 2016, 107, 288-294.
[72]
Kumar, R.N.; Dev, G.J.; Ravikumar, N.; Swaroop, D.K.; Debanjan, B.; Bharath, G.; Narsaiah, B.; Jain, S.N.; Rao, A.G. Synthesis of novel triazole/isoxazole functionalized 7-(trifluoromethyl)-pyrido[2,3-d]pyrimidine derivatives as promising anticancer and antibacterial agents. Bioorg. Med. Chem. Lett., 2016, 26(12), 2927-2930.
[73]
Hu, Y.; Lu, X.; Chen, K.; Yan, R.; Li, Q.S.; Zhu, H.L. Design, synthesis, biological evaluation and molecular modeling of 1,3,4-oxadiazoline analogs of combretastatin-A4 as novel antitubulin agents. Bioorg. Med. Chem., 2012, 20(2), 903-909.
[74]
Sun, Y.; Wang, W.; Sun, Y.; Han, M. Synthesis and biological evaluation of a novel human stem/progenitor cells proliferation activator: 4-(4-(5-mercapto-1,3,4-oxadiazol-2-yl)phenyl) thiosemicarbazide (Stemazole). Eur. J. Med. Chem., 2011, 46, 2930-2936.
[75]
Liu, K.; Lu, X.; Zhang, H.J.; Sun, J.; Zhu, H.L. Synthesis, molecular modeling and biological evaluation of 2-(benzylthio)-5-aryloxadiazole derivatives as anti-tumor agents. Eur. J. Med. Chem., 2012, 47, 473-478.
[76]
Bondock, S.; Adel, S.; Etman, H.A.; Badira, F.A. Synthesis and antitumor evaluation of some new 1,3,4-oxadiazole-based heterocycles. Eur. J. Med. Chem., 2012, 48, 192-199.
[77]
Zhang, X.M.; Qiu, M.; Sun, J.; Zhang, Y.B.; Yang, Y.S.; Wang, X.L.; Tang, J.F.; Zhu, H.L. Synthesis, biological evaluation, and molecular docking studies of 1,3,4-oxadiazole derivatives possessing 1,4-benzodioxan moiety as potential anticancer agents. Bioorg. Med. Chem., 2011, 19, 6518-6524.
[78]
Kaplancikli, Z.A.; Altintop, M.D.; Zitouni, G.T.; Ozdemir, A.; Ozic, R.; Akalin, G. Synthesis, antimicrobial activity and cytotoxicity of novel oxadiazole derivatives. J. Enzyme Inhib. Med. Chem., 2012, 27(1), 51-57.
[79]
Gudipati, R.; Anreddy, R.N.R.; Manda, S. Synthesis, characterization and anticancer activity of certain 3-4-(5-mercapto-1,3,4-oxadiazole-2-yl)phenyliminoindolin-2-one derivatives. Saudi Pharm. J., 2011, 19(3), 153-158.
[80]
Ren, J.; Wu, L.; Xin, W.Q.; Chen, X.; Hu, K. Synthesis and biological evaluation of novel 4β-(1,3,4-oxadiazole-2-amino)-podophyllotoxin derivatives. Bioorg. Med. Chem. Lett., 2012, 22(14), 4778-4782.
[81]
Husain, A.; Rashid, M.; Mishra, R.; Parveen, S.; Shin, D.S.; Kumar, D. Benzimidazole bearing oxadiazole and triazolo-thiadiazoles nucleus: Design and synthesis as anticancer agents. Bioorg. Med. Chem. Lett., 2012, 22(17), 5438-5444.
[82]
Rashid, M.; Husain, A.; Mishra, R. Synthesis of benzimidazoles bearing oxadiazole nucleus as anticancer agents. Eur. J. Med. Chem., 2012, 54, 855-866.
[83]
Sun, J.; Zhu, H.; Yang, Z.M.; Zhu, H.L. Synthesis, molecular modeling and biological evaluation of 2-aminomethyl-5-(quinolin-2-yl)-1,3,4-oxadiazole-2(3H)-thione quinolone derivatives as novel anticancer agent. Eur. J. Med. Chem., 2013, 60, 23-28.
[84]
Luo, Z.H.; He, S.Y.; Chen, B.Q.; Shi, Y.P.; Liu, Y.M.; Li, C.W.; Wang, Q.S. Synthesis and in vitro antitumor activity of 1,3,4-Oxadiazole derivatives based on benzisoselenazolone. Chem. Pharm. Bull., 2012, 60(7), 887-891.
[85]
Kumar, D.; Arun, V.; Kumar, N.M.; Acosta, G.; Noel, B.; Shah, K. A facile synthesis of novel bis-(indolyl)-1,3,4-oxadiazoles as potent cytotoxic agents. Chem. Med. Comm, 2012, 7(11), 1915-1920.
[86]
Rapolu, S.; Alla, M.; Bommena, V.R.; Murthy, R.; Jain, N.; Bommareddy, V.R.; Bommineni, M.R. Synthesis and biological screening of 5-(alkyl(1H-indol-3-yl))-2-(substituted)-1,3,4-oxadiazoles as antiproliferative and anti-inflammatory agents. Eur. J. Med. Chem., 2013, 66, 91-100.
[87]
Zhang, F.; Wang, X.L.; Shi, J.; Wang, S.F.; Yin, Y.; Yang, Y.S.; Zhang, W.M.; Zhu, H.L. Synthesis, molecular modeling and biological evaluation of N-benzylidene-2-((5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl)thio)acetohydrazide derivatives as potential anticancer agents. Bioorg. Med. Chem., 2014, 22(1), 468-477.
[88]
Tantak, M.P.; Kumar, A.; Noel, B.; Shah, K.; Kumar, D. Synthesis and biological evaluation of 2-Arylamino-5-(3′-indolyl)-1,3,4-oxadiazoles as potent cytotoxic agents. Chem. Med. Chem. Comm, 2013, 8(9), 1468-1474.
[89]
Du, K.; Cao, X.; Zhang, P.; Zheng, H. Synthesis and anti-tumor activity of glycosyl oxadiazoles derivatives. Bioorg. Med. Chem. Lett., 2014, 24(22), 5318-5320.
[90]
Zhang, K.; Wang, P.; Xuan, L.N.; Fu, X.Y.; Jing, F.; Li, S.; Liu, Y.M.; Chen, B.Q. Synthesis and antitumor activities of novel hybrid molecules containing 1,3,4-oxadiazole and 1,3,4-thiadiazole bearing Schiff base moiety. Bioorg. Med. Chem. Lett., 2014, 24(22), 5154-5156.
[91]
Ramazani, A.; Khoobi, M.; Torkaman, A.; Nasrabadi, F.Z.; Forootanfar, H.; Shakibaie, M.; Jafari, M.; Ameri, A.; Emami, S.; Faramarzi, M.A.; Foroumadi, A.; Shafiee, A. One-pot, four-component synthesis of novel cytotoxic agents 1-(5-aryl-1,3,4-oxadiazol-2-yl)-1-(1H-pyrrol-2-yl)methanamines. Eur. J. Med. Chem., 2014, 78, 151-156.
[92]
Chaaban, I.; Khawass, E.S.M.E.; Razik, H.A.A.E.; Salamouni, N.S.E.; Horcajo, M.R.; Barasoain, I.; Diaz, J.E.; Kauhaluoma, J.Y.; Moreira, V.M. Synthesis and biological evaluation of new oxadiazoline-substituted naphthalenyl acetates as anticancer agents. Eur. J. Med. Chem., 2014, 87, 805-813.
[93]
El-din, M.M.G.; El-Gamal, M.I.; Abdel-Maksoud, M.S.; Yoo, K.H.; Oh, C.H. Synthesis and in vitro antiproliferative activity of new 1,3,4-oxadiazole derivatives possessing sulfonamide moiety. Eur. J. Med. Chem., 2015, 90, 45-52.
[94]
Savariz, F.C.; Fogilo, M.A.; Ruiz, A.L.T.G.; da Costa, W.F.; Silva, M.D.M.; Santos, J.C.C.; Figueiredo, I.M.; Meyer, E.; de Carvalho, J.E.; Sarragiotto, M.H. Synthesis and antitumor activity of novel 1-substituted phenyl 3-(2-oxo-1,3,4-oxadiazol-5-yl) β-carbolines and their Mannich bases. Bioorg. Med. Chem., 2014, 22(24), 6867-6875.
[95]
Salahuddin; Mazumder, A.; Shaharyar, M. Synthesis, characterization, and in vitro Anticancer evaluation of novel 2,5-disubstituted 1,3,4-oxadiazole analogue. BioMed Res. Int., 2014, 2014, 1-14.
[96]
Ahsan, M.J.; Sharma, J.; Singh, M.; Jadav, S.S.; Yasmin, S. Synthesis and anticancer activity of N-Aryl-5-substituted-1,3,4-oxadiazol-2-amine analogues. BioMed Res. Int., 2014, 2014, 1-9.
[97]
Gurupadaswamy, H.D.; Thirusangu, P.; Avin, B.R.V.; Vigneshwaran, V.; Kumar, M.V.P.; Abhishek, T.S.; Ranganatha, V.L.; Khanum, S.A.; Prabhakar, B.T. DAO-9 (2,5-di(4-aryloylaryloxymethyl)-1,3,4-oxadiazole) exhibits p53 induced apoptogenesis through caspase-3 mediated endonuclease activity in murine carcinoma. Biomed. Pharmacother., 2014, 68(6), 791-797.
[98]
Valente, S.; Trisciuoglio, D.; Luca, T.D.; Nebbioso, A.; Labella, D.; Lenoci, A.; Bigogno, C.; Dondio, G.; Miceli, M.; Brosch, G.; Bufalo, D.D.; Altucci, L.; Mai, A. 1,3,4-oxadiazole-containing histone deacetylase inhibitors: anticancer activities in cancer cells. J. Med. Chem., 2014, 57(14), 6259-6265.
[99]
Yonova, I.M.; Osborne, C.A.; Morrissette, N.S.; Jarvo, E.R. Diaryl and heteroaryl sulfides: synthesis via sulfenyl chlorides and evaluation as selective anti-breast-cancer agents. J. Org. Chem., 2014, 79(5), 1947-1953.
[100]
Kamal, A.; Shaik, A.B.; Polepalli, S.; Reddy, V.S.; Kumar, G.B.; Gupta, S.; Krishna, K.V.S.R.; Nagabhushana, A.; Mishra, R.K.; Jain, N. Pyrazole–oxadiazole conjugates: synthesis, antiproliferative activity and inhibition of tubulin polymerization. Org. Biomol. Chem., 2014, 12(40), 7993-8007.
[101]
El-Din, M.M.G.; El-Gamal, M.I.; Abdel-Maksoud, M.S.; Yoo, K.H.; Oh, C.H. Synthesis and broad-spectrum antiproliferative activity of diarylamides and diarylureas possessing 1,3,4-oxadiazole derivatives. Bioorg. Med. Chem. Lett., 2015, 25(8), 1692-1699.
[102]
Yadagiri, B.; Gurrala, S.; Bantu, R.; Nagarapu, L.; Polepalli, S.; Srujana, G.; Jain, N. Synthesis and evaluation of benzosuberone embedded with 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole moieties as new potential anti proliferative agents. Bioorg. Med. Chem. Lett., 2015, 25(10), 2220-2224.
[103]
Barlaam, B.; Cosulich, S.; Delouvrie, B.; Ellston, R.; Fitzek, M.; Germain, H.; Green, S.; Hancox, U.; Harris, C.S.; Hudson, K.; der Brempt, C.L.V.; Lebraud, H.; Magnien, F.; Lamorlette, M.; Griffon, A.L.; Morgentin, R.; Ovury, G.; Page, K.; Pasquet, G.; Polanska, U.; Ruston, L.; Saleh, T.; Vautier, M.; Ward, L. Discovery of 1-(4-(5-(5-amino-6-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl)-1-ethyl-1, 2,4-triazol-3-yl)piperidin-1-yl)-3-hydroxypropan-1-one (AZD8835): A potent and selective inhibitor of PI3Kα and PI3Kδ for the treatment of cancers. Bioorg. Med. Chem. Lett., 2015, 25(22), 5155-5162.
[104]
Khalil, N.A.; Kamal, A.M.; Emam, S.H. Design, synthesis, and antitumor activity of novel 5-pyridyl-1,3,4-oxadiazole derivatives against the breast cancer cell line MCF-7. Biol. Pharm. Bull., 2015, 38(5), 763-773.
[105]
Mochona, B.; Mazzio, E.; Gangapuram, M.; Mateeva, N.; Redda, K.K. Synthesis of some benzimidazole derivatives bearing 1,3,4-oxadiazole moiety as anticancer agents. Chem. Sci. Trans., 2015, 4(2), 534-540.
[106]
Li, Y.T.; Wang, J.H.; Pan, C.W.; Meng, F.F.; Chu, X.Q.; Ding, Y.H.; Qu, W.Z.; Li, H.Y.; Yang, C.; Zhang, Q.; Bai, C.G.; Chen, Y. Syntheses and biological evaluation of 1,2,3-triazole and 1,3,4-oxadiazole derivatives of imatinib. Bioorg. Med. Chem. Lett., 2016, 26(5), 1419-1427.
[107]
Zhao, J.J.; Wang, X.F.; Li, B.L.; Zhang, R.L.; Li, B.; Liu, Y.M.; Li, C.W.; Liu, J.B.; Chen, B.Q. Synthesis and in vitro antiproliferative evaluation of novel nonsymmetrical disulfides bearing 1,3,4-oxadiazole moiety. Bioorg. Med. Chem. Lett., 2016, 26(18), 4414-4416.
[108]
Kumar, R.N.; Poornachandra, Y.; Nagender, P.; Kumar, G.S.; Swaroop, D.K.; Kumar, C.G.; Narsaiah, B. Synthesis of novel nicotinohydrazide and (1,3,4-oxadiazol-2-yl)-6-(trifluoromethyl)pyridine derivatives as potential anticancer agents. Bioorg. Med. Chem. Lett., 2016, 26(19), 4829-4831.
[109]
Li, Y.B.; Yan, X.; Li, R.D.; Liu, P.; Sun, S.Q.; Wang, X.; Cui, J.R.; Zhou, D.M.; Ge, Z.M.; Li, R.T. Discovery of novel heteroarylmethylcarbamodithioates as potent anticancer agents: Synthesis, structure-activity relationship analysis and biological evaluation. Eur. J. Med. Chem., 2016, 112, 217-230.
[110]
Kamal, A.; Srikanth, P.S.; Vishnuvardhan, M.V.P.S.; Kumar, G.B.; Babu, K.S.; Hussaini, S.M.A.; Kapure, J.S.; Alarifi, A. Combretastatin linked 1,3,4-oxadiazole conjugates as a potent tubulin polymerization inhibitor. Bioorg. Chem., 2016, 65, 126-136.
[111]
Rao, A.V.S.; Vardhan, M.V.P.S.V.; Reddy, N.V.S.; T.S., Reddy; Shaik, S.P.; Bagul, C.; Kamal, A. Synthesis and biological evaluation of imidazopyridinyl-1,3,4-oxadiazole conjugates as apoptosis inducers and topoisomerase IIα inhibitors. Bioorg. Chem., 2016, 69, 7-19.
[112]
Pidugu, V.R.; Yarla, N.S.; Pedada, S.R.; Kalle, A.M.; Satya, A.K. Design and synthesis of novel HDAC8 inhibitory 2,5-disubstituted-1,3,4-oxadiazoles containing glycine and alanine hybrids with anti-cancer activity. Bioorg. Med. Chem., 2016, 24(21), 5611-5617.
[113]
Tiwari, A.; Kutty, G.N.; Kumar, N.; Chaudhary, A.; Raj, P.V.; Shenoy, R.; Rao, C.M. Synthesis and evaluation of selected 1,3,4-oxadiazole derivatives for in vitro cytotoxicity and in vivo anti-tumor activity. Cytotech, 2016, 68(6), 2553-2565.
[114]
Mochona, B.; Qi, X.; Euynni, S.; Sikazwi, D.; Mateeva, N.; Soliman, K.F. Design and evaluation of novel oxadiazole derivatives as potential prostate cancer agents. Bioorg. Med. Chem. Lett., 2016, 26(12), 2847-2851.
[115]
Guo-qiang, H.; Li-li, H.; Guo-qiang, W.; Nan-nan, D.; Xiao-yi, W.; Tie-yao, C.; Jun, Y.; Wei, W.; Song-qiang, X.; Wen-long, H. Part IV: design, synthesis and antitumor activity of fluoroquinolone C-3 heterocycles: bis-oxadiazole methylsulfide derivatives derived from ciprofloxacin. Acta Pharm. Sinica., 2012, 47(8), 1017-1022.
[116]
El-Din, M.M.G.; El-Gamal, M.I.; Abdel-Maksoud, M.S.; Yoo, K.H.; Oh, C.H. Synthesis and in vitro antiproliferative activity of new 1,3,4-oxadiazole derivatives possessing sulfonamide moiety. Eur. J. Med. Chem., 2015, 90, 45-52.
[117]
El-Hamouly, W.S.; Amin, K.M.; El-Assaly, S.A.; El-Meguid, E.A.A. Synthesis and antitumor activity of some new 1,3,4-oxadiazole, pyrazole and pyrazolo[3,4-d]pyrimidine derivatives attached to 4-benzothiazol-2-yl phenyl moiety. Der Pharma Chem., 2011, 3(6), 282-292.
[118]
Fadda, A.A.; Abdel-Rahman, A.A.H.; El-Sayed, W.A.; Zidan, T.A.; Badria, F.A. Synthesis of novel 1,3,4-oxadiazole derivatives and their nucleoside analogs with antioxidant and antitumor activities. Chem. Heterocycl. Compd., 2011, 47(7), 856-864.
[119]
Du, Q.R.; Li, D.D.; Pi, Y.Z.; Li, J.R.; Sun, J.; Fang, F.; Zhong, W.Q.; Gong, H.B.; Zhu, H.L. Novel 1,3,4-oxadiazole thioether derivatives targeting thymidylate synthase as dual anticancer/ antimicrobial agents. Bioorg. Med. Chem., 2013, 21(8), 2286-2297.
[120]
Zhang, S.; Luo, Y.; He, L.Q.; Liu, Z.J.; Jiang, A.Q.; Yang, Y.H.; Zhu, H.L. Synthesis, biological evaluation, and molecular docking studies of novel 1,3,4-oxadiazole derivatives possessing benzotriazole moiety as FAK inhibitors with anticancer activity. Bioorg. Med. Chem., 2013, 21(13), 3723-3729.
[121]
Jisha, V.M.; Kamalabhai, V.K.A.; Babu, G.; Biju, C.R. Synthesis, characterization and in vitro anticancer screening of novel thiazole-1,3,4-oxadiazole hybrid analogues. J. Chem. Pharm. Res., 2013, 5(6), 64-70.
[122]
Murty, M.S.R.; Rao, B.R.; Katiki, M.R.; Nath, L.R.; Anto, R.J. Synthesis of piperazinyl benzothiazole/benzoxazole derivatives coupled with 1,3,4-oxadiazole-2-thiol: novel hybrid heterocycles as anticancer agents. Med. Chem. Res., 2013, 22(10), 4980-4991.
[123]
Tu, G.; Yan, Y.; Chen, X.; Lv, Q.; Wang, J.; Li, S. Synthesis and antiproliferative assay of 1,3,4-oxadiazole and 1,2,4-triazole derivatives in cancer cells. Drug Discov. Ther., 2013, 7(2), 58-65.
[124]
Ahsan, M.J.; Rathod, V.P.S.; Singh, M.; Sharma, R.; Jadav, S.S.; Yasmin, S. Salahuddin; Kumar, P. Synthesis, Anticancer and molecular docking studies of 2-(4-chlorophenyl)-5-aryl-1,3,4-oxadiazole analogues. Med. Chem., 2013, 3(4), 294-297.
[125]
Vinayak, A.; Sudha, M.; Lalita, K.S.; Kumar, R.P. Design, synthesis, characterization and anticancer properties of novel 2-Chloro-N-(aryl substituted) acetamide derivatives of 5-[2-(4-methoxyphenyl) pyridin-3-yl]-1, 3, 4-oxadiazole-2-thiol. Int. J. Drug Dev. Res, 2014, 6(4), 188-195.
[126]
Thasneem, C.K.; Biju, C.R.; Babu, G. Synthesis and anticancer study of chalcone linked 1,3,4-oxadiazole derivatives. Int. J. Pharma Bio Sci., 2014, 4(4), 20-28.
[127]
Antimonova, A.N.; Petrenko, N.I.; Shakirov, M.M.; Pokrovskii, M.A.; Pokrovskii, A.G.; Shults, E.E. Synthesis and cytotoxic activity of lupane triterpenoids containing 1,3,4-oxadiazoles. Chem. Nat. Compd., 2014, 50(6), 1016-1023.
[128]
Kumar, B.N.P.; Mohana, K.N.; Mallesha, L.; Veeresh, B. Synthesis and in vitro antiproliferative activity of 2,5-disubstituted-1,3,4-oxadiazoles containing trifluoromethyl benzenesulfonamide moiety. Med. Chem. Res., 2014, 23(7), 3363-3373.
[129]
Hassan, M.F.; Rauf, A.; Sherwani, A.; Owais, M. Synthesis and in vitro biological evaluation of 1,3,4-Oxadiazol-2(3H)-one and tetrahydropyridazine-3,6-dione derivatives of fatty acids. Sci. Pharm., 2015, 83(3), 429-443.
[130]
Kovacs, D.; Wolfling, J.; Szabo, N.; Szecsi, M.; Minorics, R.; Zupko, I.; Frank, E. Efficient access to novel androsteno-17-(1′,3′,4′)-oxadiazoles and 17β-(1′,3′,4′)-thiadiazoles via N-substituted hydrazone and N,N′-disubstituted hydrazine intermediates, and their pharmacological evaluation in vitro. Eur. J. Med. Chem., 2015, 98, 13-29.
[131]
Dawood, K.M.; Gombha, S.M. Synthesis and anticancer activity of 1,3,4-thiadiazole and 1,3-thiazole derivatives having 1,3,4-oxadiazole moiety. J. Heterocycl. Chem., 2015, 52(5), 1400-1405.
[132]
Nieddu, V.; Pinna, G.; Marchesi, I.; Sanna, L.; Asproni, B.; Pinna, G.A.; Bagella, L.; Murineddu, G. Synthesis and antineoplastic evaluation of novel unsymmetrical 1,3,4-oxadiazoles. J. Med. Chem., 2016, 59(23), 10451-10469.
[133]
Edayadulla, N.; Ramesh, P. Synthesis of 2,6-dicarbethoxy-3,5-diaryltetrahydro-1,4-thiazine-1,1-dioxide derivatives as potent anticonvulsant agents. Eur. J. Med. Chem., 2015, 106, 44-49.
[134]
Khanaposhtani, M.M.; Shabani, M.; Faizi, M.; Aghaei, I.; Jahani, R.; Sharafi, Z.; Zafarghandi, N.S.; Mahdavi, M.; Akbarzadeh, T.; Emami, S.; Shafiee, A.; Foroumadi, A. Design, synthesis, pharmacological evaluation, and docking study of new acidone-based 1,2,4-oxadiazoles as potential anticonvulsant agents. Eur. J. Med. Chem., 2016, 112, 91-98.
[135]
Obnniska, J.; Rapacz, A.; Rybka, S.; Gora, M.; Kaminski, K.; Salat, K.; Zmudzki, P. Synthesis and anticonvulsant activity of new amides derived from 3-methyl- or 3-ethyl-3-methyl-2,5-dioxo-pyrrlidin-1-yl-acetic acids. Bioorg. Med. Chem., 2016, 24(8), 1598-1607.
[136]
Singh, P.; Sharma, P.K.; Sharma, J.K.; Upadhyay, A.; Kumar, N. Synthesis and evaluation of substituted diphenyl-1,3,4-oxadiazole derivatives for central nervous system depressant activity. Org. Med. Chem. Lett., 2012, 2(8), 1-10.
[137]
Faizi, M.; Sheikhha, M.; Ahangar, N.; Ghomi, H.T.; Shafaghi, B.; Shafiee, A.; Tabatabai, S. Design, synthesis and pharmacological evaluation of novel 2-[2-(2-Chlorophenoxy) phenyl]-1,3,4-oxadiazole derivatives as benzodiazepine receptor agonists. Iran. J. Pharm. Res., 2012, 11(1), 83-90.
[138]
Tabatabai, S.A.; Lashkari, S.B.; Zarrindast, M.R.; Gholibeikian, M.; Shafiee, A. Design, synthesis and anticonvulsant activity of 2-(2-Phenoxy) phenyl- 1,3,4-oxadiazole derivatives. Iran. J. Pharm. Res., 2013, 12, 105-111.
[139]
Mashayekh, S.; Rahmanipour, N.; Mahmoodi, B.; Ahmadi, F.; Motaharian, D.; Shahhosseini, S.; Shafaroodi, H.; Banafshe, H.R.; Shafiee, A.; Navidpour, L. Synthesis, receptor affinity and effect on pentylenetetrazole-induced seizure threshold of novel benzodiazepine analogues: 3-Substituted 5-(2-phenoxybenzyl)-4H-1,2,4-triazoles and 2-amino-5-(phenoxybenzyl)-1,3,4-oxadiazoles. Bioorg. Med. Chem., 2014, 22(6), 1929-1937.
[140]
Harish, K.P.; Mohana, K.N.; Mallesha, L.; Veeresh, B. Synthesis and in vivo anticonvulsant activity of 2-Methyl-2-[3-(5-piperazin-1-yl-[1,3,4]oxadiazol-2-yl)-phenyl]-propionitrile derivatives. Arch. Pharm. Chem. Life Sci, 2014, 347(4), 256-267.
[141]
Rajak, H.; Thakur, B.S.; Singh, A.; Raghuvanshi, K.; Sah, A.K.; Veerasamy, R.; Sharma, P.C.; Pawar, R.S.; Kharya, M.D. Novel limonene and citral based 2,5-disubstituted-1,3,4-oxadiazoles: A natural product coupled approach to semicarbazones for antiepileptic activity. Bioorg. Med. Chem. Lett., 2013, 23(3), 864-868.
[142]
Gupta, A.; Kashaw, S.K.; Jain, N.; Rajak, H.; Soni, A.; Stables, J.P. Design and synthesis of some novel 3-[5-(4-substituted) phenyl-1,3,4-oxadiazole-2yl]-2-phenylquinazoline-4(3H)-ones as possible anticonvulsant agent. Med. Chem. Res., 2011, 20(9), 1638-1642.
[143]
Jain, N.; Kashaw, S.K.; Agrawal, R.K.; Gupta, A.; Soni, A. Synthesis, anticonvulsant and neurotoxic activity of some new 2,5-disubstituted-1,3,4-oxadiazoles. Med. Chem. Res., 2011, 20(9), 1696-1703.
[144]
Siddiqui, N.; Akhtar, M.J.; Yar, M.S.; Ahuja, P.; Ahsan, W.; Ahmed, S. Substituted phenyl containing 1,3,4-oxadiazole-2-yl-but-2-enamides: synthesis and preliminary evaluation as promising anticonvulsants. Med. Chem. Res., 2014, 23(11), 4915-4925.
[145]
Subramanian, G.; Rajeev, C.P.B.; Mohan, C.D.; Sinha, A.; Chu, T.T.T.; Anusha, S.; Ximei, H.; Fuchs, J.E.; Bender, A.; Rangappa, K.S.; Chandramohanadas, R. Basappa. Synthesis and in vitro evaluation of hydrazinyl phthalazines against malaria parasite. Plasmodium. Bioorg. Med. Chem. Lett, 2016, 26(14), 3300-3306.
[146]
Aminake, M.N.; Mahajan, A.; Kumar, V.; Hans, R.; Weisner, L.; Taylor, D.; de Kock, C.; Grobler, A.; Smith, P.J.; Kirschner, M.; Rethwilm, A.; Pradel, G.; Chibale, K. Synthesis and evaluation of hybrid drugs for a potential HIV/AIDS-malaria combination therapy. Bioorg. Med. Chem., 2012, 20(17), 5277-5289.
[147]
Hansen, F.K.; Sumanadasa, S.D.M.; Stenzel, K.; Duffy, S.; Meister, S.; Marek, L.; Schmetter, R.; Kuna, K.; Hamacher, A.; Mordmuller, B.; Kassack, M.U.; Winzeler, E.A.; Avery, V.M.; Andrews, K.T.; Kurz, T. Discovery of HDAC inhibitors with potent activity against multiple malaria parasite life cycle stages. Eur. J. Med. Chem., 2014, 82, 204-213.
[148]
Boudhar, A.; Ng, X.W.; Loh, C.Y.; Chia, W.N.; Tan, Z.M.; Nosten, F.; Dymock, B.W.; Tan, K.S.W. Overcoming chloroquine resistance in malaria: design, synthesis and structure-activity relationships of novel chemoreversal agents. Eur. J. Med. Chem., 2016, 119, 231-249.
[149]
Rackham, M.D.; Brannigan, J.A.; Rangachari, K.; Meister, S.; Wilkinson, A.J.; Holder, A.A.; Leatherbarrow, R.J.; Tate, E.W. Design and synthesis of high affinity inhibitors of Plasmodium falciparum and Plasmodium vivax N-Myristoyltransferases directed by Ligand Efficiency Dependent Lipophilicity (LELP). J. Med. Chem., 2014, 57, 2773-2788.
[150]
Radini, I.A.M.; Elsheikh, T.M.Y.; Telbani, E.M.E.; Khidre, R.E. New potential antimalarial agents: design, synthesis and biological evaluation of some novel quinoline derivatives as antimalarial agents. Molecules, 2016, 21, 1-12.
[151]
Desai, S.R.; Laddi, U.V.; Bennur, R.S.; Benur, S.C. Synthesis and antimicrobial activities of some new Azetidin-2-ones and Thiazolidin-4-ones. Indian J. Pharm. Sci., 2011, 73(4), 478-482.
[152]
Zareef, M.; Iqbal, R.; Mirza, B.; Khan, K.M.; Manan, A.; Asim, F.; Khan, S.W. Synthesis and antimicrobial activity of some derivatives of acylhydrazine including novel benzenediazasulfonamides. ARKIVOC, 2008, ii, 141-152.
[153]
Prakash, C.R.; Raja, S. Synthesis, characterization and in vitro antimicrobial activity of some novel 5-substituted Schiff and Mannich base of isatin derivatives. J. Saudi Chem. Soc., 2013, 17(3), 337-344.
[154]
Li, Y.; Luo, Y.; Hu, Y.; Zhu, D.D.; Zhang, S.; Liu, Z.J.; Gong, H.B. Design, synthesis and antimicrobial activities of nitroimidazole derivatives containing 1,3,4-oxadiazole scaffold as FabH inhibitors. Bioorg. Med. Chem., 2012, 20(14), 4316-4322.
[155]
Malhotra, M.; Hans, P.; Sharma, S.; Deep, A.; Phogat, P. Synthesis and characterization of (Z)-N-(1-[2-3-[(Dimehtylamino)methyl)]-2-methoxyohenyl-5-(pyridine-4-yl)-1,3,4-oxadiazol-3(2H)-yl]ethylidene)benzenamine derivatives as potent antifungal agents. Acta Pol. Pharm., 2012, 69(3), 433-438.
[156]
Ali, O.M.; El-Sayed, W.A.; Eid, S.A.; Abdelwahed, N.A.M.; Abdel-Rahman, A.A.H. Antimicrobial activity of new synthesized [(oxadiazolyl)]methyl]phenytoin derivatives. Acta Pol. Pharm.-. Drug Res., 2012, 69(4), 657-667.
[157]
de Oliveira, C.S.; Lira, B.F.; Falcao-Silva, V.D.S.; Junior, J.P.S.; Barbosa-Filho, J.M.; Athayde-Filho, P.F.D. Synthesis, molecular properties prediction, and anti-staphylococcal activity of N-Acylhydrazones and new 1,3,4-oxadiazole derivatives. Molecules, 2012, 17(5), 5095-5107.
[158]
El-Sadek, M.M.; Hassan, S.Y.; El-Dayem, N.S.A.; Yacout, G.A. 5-(5-Aryl-1,3,4-oxadiazole-2-carbonyl)furan-3-carboxylate and new cyclic C-glycoside analogues from carbohydrate precursors with MAO-B, antimicrobial and antifungal activities. Molecules, 2012, 17(6), 7010-7027.
[159]
Desai, N.C.; Bhatt, N.; Somani, H.; Trivedi, A. Synthesis, antimicrobial and cytotoxic activities of some novel thiazole clubbed 1,3,4-oxadiazoles. Eur. J. Med. Chem., 2013, 67, 54-59.
[160]
Shyma, P.C.; Kalluraya, B.; Peethambar, S.K.; Telkar, S.; Arulmoli, T. Synthesis, characterization and molecular docking studies of some new 1,3,4-oxadiazolines bearing 6-methylpyridine moiety for antimicrobial property. Eur. J. Med. Chem., 2013, 68, 394-404.
[161]
Ningaiah, S.; Bhadraiah, U.K.; Doddaramappa, S.D.; Keshavamurthy, S.; Javarasetty, C. Novel pyrazole integrated 1,3,4-oxadiazoles: Synthesis, characterization and antimicrobial evaluation. Bioorg. Med. Chem. Lett., 2014, 24(1), 245-248.
[162]
Li, L.; Ding, H.; Wang, B.; Yu, S.; Zou, Y.; Chai, X.; Wu, Q. Synthesis and evaluation of novel azoles as potent antifungal agents. Bioorg. Med. Chem. Lett., 2014, 24(1), 192-194.
[163]
Liu, J.C.; Zheng, C.J.; Wang, M.X.; Li, Y.R.; Ma, L.X.; Hou, S.P.; Piao, H.R. Synthesis and evaluation of the antimicrobial activities of 3-((5-phenyl-1,3,4-oxadiazol-2-yl)methyl)-2-thioxothiazolidin-4-one derivatives. Eur. J. Med. Chem., 2014, 74, 405-410.
[164]
Liao, J.; Yang, F.; Zhang, L.; Chai, X.; Zhao, Q.; Yu, S.; Zou, Y.; Meng, Q.; Wu, Q. Synthesis and biological evaluation of novel fluconazole analogues bearing 1,3,4-oxadiazole moiety as potent antifungal agents. Arch. Pharm. Res., 2015, 38(4), 470-479.
[165]
Bala, S.; Kamboj, S.; Kajal, A.; Saini, V.; Prasad, D.N. 1,3,4-Oxadiazole derivatives: Synthesis, characterization, antimicrobial potential, and computational studies. BioMed Res. Int., 2014, 2014, 1-18.
[166]
Pal, D.; Tripathi, R.; Pandey, D.D.; Mishra, P. Synthesis, characterization, antimicrobial and pharmacological evaluation of some 2,5-disubstituted sulfonyl amino 1,3,4-oxadiazole and 2-amino-disubstituted 1,3,4-thiadiazole derivatives. J. Adv. Pharm. Technol. Res., 2014, 5(4), 196-201.
[167]
Wani, M.Y.; Ahmad, A.; Shiekh, R.A.; Ghamdi, K.J.A.; Sobral, A.J.F.N. Imidazole clubbed 1,3,4-oxadiazole derivatives as potential antifungal agents. Bioorg. Med. Chem., 2015, 23(15), 4172-4180.
[168]
Wang, P.Y.; Zhou, L.; Zhou, J.; Wu, Z.B.; Xue, W.; Song, B.A.; Yang, S. Synthesis and antibacterial activity of pyridinium-tailored 2,5-substituted-1,3,4-oxadiazole thioether/sulfoxide/sulfone derivatives. Bioorg. Med. Chem. Lett., 2016, 26(4), 1214-1217.
[169]
Sindhe, M.A.; Bodke, Y.D.; Kenchappa, R.; Telkar, S.; Chandrashekar, A. Synthesis of a series of novel 2,5-disubstituted-1,3,4-oxadiazole derivatives as potential antioxidant and antibacterial agents. J. Chem. Biol., 2016, 9(3), 79-90.
[170]
Nimbalkar, U.D.; Tupe, S.G.; Vazquez, J.A.S.; Khan, F.A.K.; Sangshetti, J.N.; Nikalje, A.P.G. Ultrasound- and molecular sieves-assisted synthesis, molecular docking and antifungal evaluation of 5-(4-(Benzyloxy)-substituted phenyl)-3-((phenylamino)methyl)-1,3,4-oxadiazole-2(3H)-thiones. Molecules, 2016, 21(5), 1-13.
[171]
Shridhar, J.; Keshavayya, H.J. Hoskeri; Ali, R.A.S. Synthesis of some novel Bis 1,3,4-oxadiazole fused azo dye derivatives as potent antimicrobial agents. Int. Res. J. Pure Appl. Chem., 2011, 1, 119-129.
[172]
Salimon, J.; Salih, N.; Yousif, E.; Hameed, A.; Kareem, A. Synthesis and pharmacological evaluation of 9(10H)-acridone bearing 1,3,4-oxadiazole derivatives as antimicrobial agents. Arab. J. Chem., 2010, 3(4), 205-210.
[173]
Hemavathi, S.N.; Kumar, B.K.V.; Rai, K.M.L. Synthesis and Biological Screening of some new 2,5-disubstituted 1,3,4-oxadiazoles. Int. J. Pharm. Pharm. Sci., 2011, 3(4), 110-114.
[174]
Deshmukh, R.; Jha, A.K.; Thakur, A.S.; Dewangan, D. Synthesis and antibacterial activity of some 1,3,4-oxadiazole derivatives and their thione derivatives. Int. J. Res. Pharm. Biomed. Sci., 2011, 2, 215-219.
[175]
Parikh, P.K. Marvaniya; Sen, D.J. Synthesis and biological evaluation of 1,3,4-oxadiazole derivatives as potential antibacterial and antifungal agents. Int. J. Drug Dev. Res, 2011, 3(2), 248-255.
[176]
Ramaprasad, G.C.; Kalluraya, B.; Kumar, B.S.; Mallya, S. Synthesis, antibacterial and antifungal activities of some novel 1,3,4-oxadiazole analogues. Int. J. Pharm. Pharm. Sci., 2012, 4(4), 210-213.
[177]
Salahuddin; Shaharyar, M.; Mazumder, A.; Abdullah, M.M. Synthesis, characterization and antimicrobial activity of 1,3,4-oxadiazole bearing 1H-bezimidazle derivatives. Arab. J. Chem., 2012.
[http://dx.doi.org/10.1016/j.arabjc.2012.10.010]
[178]
Prajapati, S.D.; Thakor, M.K. Synthesis and antimicrobial evaluation of some novel heterocyclic compounds. J. Curr. Chem. Pharm. Sci, 2013, 3, 176-180.
[179]
Khalid, H.; Rehman, A.U.; Abbasi, M.A.; Malik, A.; Rasool, S.; Nafeesa, K.; Ahmad, I.; Afzal, S. Synthesis, spectral analysis and anti-bacterial study of N-substituted derivatives of 2-(5-(1-(phenylsulfonyl)piperidin-4-yl)-1,3,4-oxadiazol-2-ylthio)acetamide. J. Saudi Chem. Soc., 2013, 20(1), S615-S623.
[180]
Malhotra, M.; Rawal, R.K.; Malhotra, D.; Dhingra, R.; Deep, A.; Sharma, P.C. Synthesis, characterization and pharmacological evaluation of (Z)-2-(5-(biphenyl-4-yl)-3-(1-(imino)ethyl)-2,3-dihydro-1,3,4-oxadiazol-2-yl)phenol derivatives as potent antimicrobial and antioxidant agents. Arab. J. Chem., 2013.
[http://dx.doi.org/10.1016/j.arabjc.2013.01.005]
[181]
Farshori, N.N.; Rauf, A.; Siddiqui, M.A.; Al-Sheddi, E.S.; Al-Oqail, M.M. A facile one-pot synthesis of novel 2,5-disubstituted- 1,3,4-oxadiazoles under conventional and microwave conditionsand evaluation of their in vitro antimicrobial activities. Arabian J. Chem., 2013, http://dx.doi.org/10.1016/j.arabjc.2013.11.010.
[182]
Al-Azzawi, A.M.; Hamd, A.S. Synthesis, characterization and antimicrobial activity evaluation of new cyclic imides containing 1,3,4-thiadiazole and 1,3,4-oxadiazole moieties. Int. J. Res. Pharm. Chem., 2013, 3(4), 890-897.
[183]
Kumar, R.; Yar, M.S.; Rai, A.K.; Chaturvedi, S. Synthesis and biological evaluation of some novel 1,3,4-oxadiazoles derived from bi phenyl 4- carboxylic acid. Der. Pharm. Lett, 2013, 5(1), 366-370.
[184]
Kumar, B.N.P.; Mohana, K.N.; Mallesha, L.; Harish, K.P. Synthesis and in vitro antimicrobial evaluation of new 1,3,4-oxadiazoles bearing 5-chloro-2-methoxyphenyl moiety. Int. J. Med. Chem., 2013, 2013, 1-6.
[185]
Bhat, M.A.; Al-Omar, M.A.; Siddiqui, N. Antimicrobial activity of Schiff bases of coumarin-incorporated 1,3,4-oxadiazole derivatives: an in vitro evaluation. Med. Chem. Res., 2013, 22(9), 4455-4458.
[186]
Kumar, S.; Pandey, H.N. Electrochemical synthesis of 2-amino-5-substituted-1,3,4-oxadiazole derivatives and evaluation of antibacterial activity. Indian J. Chem., 2013, 52B, 252-258.
[187]
Zhang, M.Z.; Mulholland, N.; Beattie, D.; Irwin, D.; Gu, Y.C.; Chen, Q.; Yang, G.F.; Clough, J. Synthesis and antifungal activity of 3-(1,3,4-oxadiazol-5-yl)-indoles and 3-(1,3,4-oxadiazol-5-yl)methyl-indoles. Eur. J. Med. Chem., 2013, 63, 22-32.
[188]
Moger, M.; Satam, V.; Govindaraju, D.R.C.; Paniraj, A.S.; Gopinath, V.S.; Hindupur, R.M.; Pati, H.N. Synthesis and antimicrobial properties of 1,3,4-oxadiazole analogs containing dibenzosuberane moiety. J. Braz. Chem. Soc., 2014, 25(1), 104-111.
[189]
Girish, V.; Khanum, N.F.; Gurupadaswamy, H.D.; Khanum, S.A. Synthesis and evaluation of in vitro antimicrobial activity of novel 2-[2-(Aroyl)aroyloxy]methyl-1,3,4-Oxadiazoles. Russ. J. Bioorganic Chem., 2014, 40(3), 330-335.
[190]
Murty, M.S.R.; Penthala, R.; Buddana, S.K.; Prakasham, R.S.; Das, P.; Polepalli, S.; Jain, N.; Bojja, S. Recyclable CuO nanoparticles-catalyzed synthesis of novel-2,5-disubstituted 1,3,4-oxadiazoles as antiproliferative, antibacterial, and antifungal agents. Med. Chem. Res., 2014, 23(10), 4579-4594.
[191]
Gul, S.; Rehman, A.U.; Abbasi, M.A.; Khan, K.M.; Nafeesa, K.; Siddiqa, A.; Akhtar, M.N.; Shahid, M.; Subhani, Z. Synthesis, antimicrobial evaluation and hemolytic activity of 2-[[5-alkyl/aralkyl substituted-1,3,4-oxadiazol-2-yl]thio]-N-[4-(4-morpholinyl)phenyl]acetamide derivatives. J. Saudi Chem. Soc., 2014.
[http://dx.doi.org/10.1016/j.jscs.2014.04.005]
[192]
Desai, N.C.; Dodiya, A.M. Synthesis, characterization and in vitro antimicrobial screening of quinoline nucleus containing 1,3,4-oxadiazole and 2-azetidinone derivatives. J. Saudi Chem. Soc., 2015, 18(5), 425-431.
[193]
Desai, N.C.; Dodiya, A.M.; Rajpara, K.M.; Rupala, Y.M. Synthesis and antimicrobial screening of 1,3,4-oxadiazole and clubbed thiophene derivatives. J. Saudi Chem. Soc., 2014, 18(3), 255-261.
[194]
Su, S.; Zhou, X.; Zhou, Y.; Liao, G.; Shi, L.; Yang, X.; Zhang, X.; Jin, L. Synthesis and biological evaluation of novel sulfone derivatives containing 1,3,4-oxadiazole moiety. World J. Org. Chem, 2014, 2(1), 18-27.
[195]
Malladi, S.; Isloor, A.M.; Peethambar, S.K.; Fun, H.K. Synthesis and biological evaluation of newer analogues of 2,5-disubstituted 1,3,4-oxadiazole containing pyrazole moiety as antimicrobial agents. Arab. J. Chem., 2014, 7(6), 1185-1191.
[196]
Swarankar, D.; Ameta, R.; Vyas, R. Microwave-assisted synthesis of some 1,3,4-oxadiazole derivatives and evaluation of their antibacterial and antifungal activity. Org. Chem. Int., 2014, 2014, 1-6.
[197]
Grewal, A.S.; Redhu, S. Synthesis, antibacterial and antifungal activity of 2,5-disubstituted-1,3,4-oxadiazole derivatives. Int. J. Pharm. Tech. Res., 2014, 6(7), 2015-20121.
[198]
Rasool, S.; Rehman, A.U.; Abbasi, M.A.; Gul, S.; Akhtar, M.N.; Ahmad, I.; Afzal, S. Synthesis of N′-Substituted-2-(5-(4-Chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetohydrazide derivatives as suitable antibacterial agents. Trop. J. Pharm. Res., 2015, 14(6), 1081-1088.
[199]
Rajak, H.; Patel, P.; Singh, A.; Jain, D.K.; Patel, V.K. Antimicrobial potential of some novel N-aryldithiocarbamate based 1,3,4- oxadiazoles. Int. J. Res. Stud. Biosci.,2015, 79-82.
[200]
Shi, Z.; Zhao, Z.; Huang, M.; Fu, X. Ultrasound-assisted, one-pot, three-component synthesis and antibacterial activities of novel indole derivatives containing 1,3,4-oxadiazole and 1,2,4-triazole moieties. C. R. Chim., 2015, 18(12), 1320-1327.
[201]
Rehman, A.U.; Siddiqa, A.; Abbasi, M.A.; Rasool, S.; Siddiqui, S.Z.; Ahmad, I.; Afzal, S. Synthesis of some new 5-substituted-2-((6-chloro-3,4-methylenedioxyphenyl)methylthio)-1,3,4-oxadiazole derivatives as suitable antibacterial inhibitors. Bull. Fac. Pharm. Cairo Univ., 2015, 53(1), 37-43.
[202]
Pagare, A.H.; Kankate, R.S.; Shaikh, A.R. Synthesis and antimicrobial evaluation of newer 1,3,4-oxadiazole derivatives containing R-phenyl moiety under conventional conditions. Res. J. Chem. Environ. Sci, 2016, 4(2), 45-50.
[203]
Desai, N.C.; Bhatt, N.; Dodiya, A.; Karkar, T.; Patel, B.; Bhatt, M. Synthesis, characterization and antimicrobial screening of thiazole based 1,3,4-oxadiazoles heterocycles. Res. Chem. Intermed., 2016, 42(4), 3039-3053.
[204]
Gurunanjappa, P.; Kariyappa, A.K. Design, synthesis and biological evaluation of 1,3,4-oxadiazoles/thiadiazoles bearing pyrazole scaffold as antimicrobial and antioxidant candidates. Curr. Chem. Lett, 2016, 5(3), 109-122.
[205]
Desai, N.C.; Bhatt, N.B.; Somani, H.C.; Bhatt, K.A. Synthesis and antimicrobial activity of some thiazole and 1,3,4-oxadiazole hybrid heterocycles. Indian J. Chem., 2016, 55B(01), 94-101.
[206]
Neeraja, P.; Srinivas, S.; Mukkanti, K.; Dubey, P.K.; Pal, S. 1H-1,2,3-Triazolyl-substituted 1,3,4-oxadiazole derivatives containing structural features of ibuprofen/naproxen: Their synthesis and antibacterial evaluation. Bioorg. Med. Chem. Lett., 2016, 26(21), 5212-5217.
[207]
He, H.; Wang, W.; Zhou, Y.; Xia, Q.; Ren, Y.; Feng, J.; Peng, H.; He, H.; Feng, L. Rational design, synthesis and biological evaluation of 1,3,4-oxadiazole pyrimidine derivatives as novel pyruvate dehydrogenase complex E1 inhibitors. Bioorg. Med. Chem., 2016, 24(8), 1879-1888.
[208]
Joshi, S.D.; Kumar, D.; Dixit, S.R.; Tigadi, N.; More, U.A.; Lherbet, C.; Aminabhavi, T.M.; Yang, K.S. Synthesis, characterization and antitubercular activities of novel pyrrolyl hydrazones and their Cu-complexes. Eur. J. Med. Chem., 2016, 121, 21-39.
[209]
Naidu, K.M.; Srinivasarao, S.; Agnieszka, N.; Ewa, A.K.; Kumar, M.M.K.; Sekhar, K.V.G.C. Seeking potent anti-tubercular agents: design, synthesis, anti-tubercular activity and docking study of various ((triazoles/indole)-piperazin-1-yl/1,4-diazepan-1-yl)benzo[d]isoxazole derivatives. Bioorg. Med. Chem. Lett., 2016, 26(9), 2245-2250.
[210]
Rohde, K.H.; Michaels, H.A.; Nefzi, A. Synthesis and antitubercular activity of 1,2,4-trisubstituted piperazines. Bioorg. Med. Chem. Lett., 2016, 26(9), 2206-2209.
[211]
Patel, R.V.; Patel, P.K.; Kumari, P.; Rajani, D.P.; Chikhalia, K.H. Synthesis of benzimidazolyl-1,3,4-oxadiazol-2ylthio-N-phenyl (benzothiazolyl) acetamides as antibacterial, antifungal and antituberculosis agents. Eur. J. Med. Chem., 2012, 53, 41-51.
[212]
Rane, R.A.; Bangalore, P.; Borhade, S.D.; Khandare, P.K. Synthesis and evaluation of novel 4-nitropyrrole-based 1,3,4-oxadiazole derivatives as antimicrobial and anti-tubercular agents. Eur. J. Med. Chem., 2013, 70, 49-58.
[213]
Bhat, M.A. Synthesis and anti-mycobacterial activity of new 4-thiazolidinone and 1,3,4-oxadiazole derivatives of isoniazid. Acta Pol. Pharm. Drug Res, 2014, 71(5), 763-770.
[214]
Mathew, B.; Suresh, J.; Mathew, G.E.; Sonia, G.; Krishnan, G.K. Design, synthesis, toxicity estimation and molecular docking studies of N-(furan-2-yl)-1-(5-substituted)phenyl-1,3,4-oxadiazol-2-yl) methanimine as antitubercular agents. Indian J. Pharm. Sci., 2014, 76(5), 401-406.
[215]
Desai, N.C.; Somani, H.; Trivedi, A.; Bhatt, K.; Nawale, L.; Khedkar, V.M.; Jha, P.C.; Sarkar, D. Synthesis, biological evaluation and molecular docking study of some novel indole and pyridine based 1,3,4-oxadiazole derivatives as potential antitubercular agents. Bioorg. Med. Chem. Lett., 2016, 26(7), 1776-1783.
[216]
Dhumal, S.T.; Deshmukh, A.R.; Bhosle, M.R.; Khedkar, V.M.; Nawale, L.U.; Sarkar, D.; Mane, R.A. Synthesis and antitubercular activity of new 1,3,4-oxadiazoles bearing pyridyl and thiazolyl scaffolds. Bioorg. Med. Chem. Lett., 2016, 26(15), 3646-3651.
[217]
Karbanovich, G.; Zemanova, J.; Smutny, T.; Szekely, R.; Sarkan, M.; Centarova, I.; Vocat, I.; Pavkova, A.; Conka, P.; Nemecek, J.; Stolarikova, J.; Vejsova, M.; Vavrova, K.; Klimesova, V.; Hrabalek, A.; Pavek, P.; Cole, S.T.; Mikusova, K.; Roh, J. Development of 3,5-Dinitrobenzylsulfanyl-1,3,4-oxadiazoles and thiadiazoles as selective antitubercular Agents active against replicating and nonreplicating Mycobacterium tuberculosis. J. Med. Chem., 2016, 59(6), 2362-280.
[218]
Chitre, T.S.; Panda, S.; Patil, S.M.; Chothe, A.S.; Vignesh, G.; Salake, A.B.; Kathiravan, M.K. Novel 1,3,4-(thiadiazol-2-ylamino)methyl-5-(pyridin-4-yl)-1,3,4-oxadiazol-2-thiones: Synthesis, docking and antimycobacterial testing. Adv. Biol. Chem., 2011, 1, 7-14.
[219]
Gobis, K.; Foks, H.; Augustynowicz-Kopec, E.; Napiorkowska, A.; Szczesio, M.; Olczak, A.; Glowka, M.L. Synthesis, characterization, and tuberculostatic activity of novel 2-(4-nitrobenzoyl)-hydrazinecarbodithioic acid derivatives. Monatsh. Chem., 2012, 143(4), 607-617.
[220]
Das, R.; Asthana, G.S.; Suri, K.A.; Mehta, D.K.; Asthana, A. Synthesis and assessment of antitubercular and antimicrobial activity of some novel triazole and tetrazolo-fused 1,3,4-oxadiazole molecules containing pyrazine moiety. J. Pharm. Sci. Res., 2015, 7(10), 806-811.
[221]
Desai, N.C.; Trivedi, A.R.; Vaghani, H.V.; Somani, H.C.; Bhatt, K.A. Synthesis and biological evaluation of 1,3,4-oxadiazole bearing dihydropyrimidines as potential antitubercular agents. Med. Chem. Res., 2016, 25(2), 329-338.
[222]
Karabanovich, G.; Nemecek, J.; Valaskova, L.; Carazo, A.; Konecna, K.; Stolarikova, J.; Hrabalek, A.; Pavlis, O.; Pavek, P.; Vavrova, K.; Roh, J.; Klimesova, V. S-substituted 3,5-dinitrophenyl 1,3,4-oxadiazole-2-thiols and tetrazole-5-thiols as highly efficient antitubercular agents. Eur. J. Med. Chem., 2017, 126, 369-383.
[223]
He, L.; Pei, H.; Ma, L.; Pu, Y.; Chen, J.; Liu, Z.; Ran, Y.; Lei, L.; Fu, S.; Tang, M.; Peng, A.; Long, C.; Chen, L. Synthesis and lipid-lowering evaluation of 3-methyl-1H-purine-2,6-dione derivatives as potent and orally available anti-obesity agents. Eur. J. Med. Chem., 2014, 87, 595-610.
[224]
Chaiittaiyanan, R.; Chayopas, P.; Rattanathongkom, A.; Tippayawat, P.; Sutthaunt, K. Anti-obesity potential of corn skills: relationships of phytochemicals and antioxidation, anti-pre-adipocyte proliferation, anti-adipogenesis, and lipolysis induction. J. Funct. Foods, 2016, 23, 497-510.
[225]
Alvarado, M.; Decara, J.; Luque, M.J.; Hernandez-Folgado, L.; Gomez-Canas, M.; Gomez-Ruiz, M.; Fernandez-Ruiz, J.; Elguero, J.; Jagerovic, N.; Serrano, A.; Goya, P.; de Fonseca, F.R. Novel antiobesity agents: synthesis and pharmacological evaluation of analogues of Rimonabant and of LH21. Bioorg. Med. Chem., 2013, 21(7), 1708-1716.
[226]
McCoull, W.; Addie, M.S.; Birch, A.M.; Birtles, S.; Buckett, L.K.; Butlin, R.J.; Bowker, S.S.; Boyd, S.; Champman, S.; Davies, R.D.M.; Donald, C.S.; Green, C.P.; Jenner, C.; Kemmitt, P.D.; Leach, A.G.; Moody, G.C.; Gutierrez, P.M.; Newcombe, N.J.; Nowak, T.; Packer, M.J.; Plowright, A.T.; Revill, J.; Schofield, P.; Sheldon, C.; Stokes, S.; Turnbull, A.V.; Wang, S.J.Y.; Whalley, D.P.; Wood, J.W. Identification, optimisation and in vivo evaluation of oxadiazole DGAT-1 inhibitors for the treatment of obesity and diabetes. Bioorg. Med. Chem. Lett., 2012, 22(12), 3873-3878.
[227]
Point, V.; Kumar, K.V.P.P.; Marc, S.; Delorme, V.; Parsiegla, G.; Amara, S.; Carriere, F.; Buono, G.; Fotiadu, F.; Canaan, S.; Leclaire, J.; Cavalier, J.F. Analysis of the discriminative inhibition of mammalian digestive lipases by 3-phenyl substituted 1,3,4-oxadiazol-2(3H)-ones. Eur. J. Med. Chem., 2012, 58, 452-463.
[228]
Lee, Y.H.; Kim, H.J.; Yoo, H.; Jung, S.Y.; Kwon, B.J.; Kim, N.J.; Jin, C.; Lee, Y.S. Synthesis of (2-amino)ethyl derivatives of quercetin-3-O-metyl ether and their antioxidant and neuroprotective effects. Bioorg. Med. Chem., 2015, 23(15), 4970-4979.
[229]
Kim, J.H.; Shyam, P.K.; Kim, M.J.; Lee, H.J.; Lee, J.T.; Jang, H.Y. Enantioselective synthesis and antioxidant activity of 3,4,5-substituted piperidine derivatives. Bioorg. Med. Chem. Lett., 2016, 26(13), 3119-3121.
[230]
Sahu, P.K. Design, structure activity relationship, cytotoxicity and evaluation of antioxidant activity of curcumin derivatives/ analogues. Eur. J. Med. Chem., 2009, 121, 510-516.
[231]
Padmavathi, V.; Reddy, G.D.; Reddy, S.N.; Mahesh, K. Synthesis and biological activity of 2-(bis((1,3,4-oxadiazolyl/1,3,4-thiadiazolyl)methylthio)methylene)malononitriles. Eur. J. Med. Chem., 2016, 26, 1367-1373.
[232]
Kumar, B.V.; Naik, H.S.B.; Girija, D.; Sharath, N.; Sudeep, H.V.; Hoskeri, H.J. Synthesis and biological evaluation of new tetra-aza macrocyclic scaffold constrained oxadiazole, thiadiazole and triazole rings. Arch. Pharm. Chem. Life Sci, 2012, 345(3), 240-249.
[233]
Kotaiah, Y.; Harikrishna, N.; Nagaraju, K.; Rao, C.V. Synthesis and antioxidant activity of 1,3,4-oxadiazole tagged thieno[2,3-d]pyrimidine derivatives. Eur. J. Med. Chem., 2012, 58, 340-345.
[234]
Kerimov, I.; Kilcigil, G.A.; Ozdamar, E.D.; Eke, B.C.; Coban, T.; Ozbey, S.; Kazak, C. Design and one-pot and microwave-assisted synthesis of 2-Amino/5-Aryl-1,3,4-oxadiazoles bearing a benzimidazole moiety as antioxidants. Arch. Pharm. Chem. Life Sci, 2012, 345(7), 549-556.
[235]
Reddy, G.M.; Muralikrishna, A.; Padmavathi, V.; Padmaja, A.; Tilak, T.K.; Rao, C.A. Synthesis and antioxidant activity of styrylsulfonylmethyl 1,3,4-oxadiazoles, pyrazolyl/isoxazolyl-1,3,4-oxadiazoles. Chem. Pharm. Bull., 2013, 61(12), 1291-1297.
[236]
Ma, L.; Xiao, Y.; Li, C.; Xie, Z.L.; Li, D.D.; Wang, Y.T.; Ma, H.T.; Zhu, H.L.; Wang, M.H.; Ye, Y.H. Synthesis and antioxidant activity of novel Mannich base of 1,3,4-oxadiazole derivatives possessing 1,4-benzodioxan. Bioorg. Med. Chem., 2013, 21(21), 6763-6770.
[237]
Basha, N.M.; Lavanya, G.; Padmaja, A.; Padmavathi, V. Synthesis and antioxidant activities of Acetamidomethylsulfonyl Bis heterocycles-oxazolyl/Thiazolyl/imidazolyl-1,3,4-oxadiazoles. Arch. Pharm. Chem. Life Sci, 2013, 346(7), 511-520.
[238]
Mohana, K.N.; Kumar, C.B.P. Synthesis and antioxidant activity of 2-Amino-5-methylthiazol derivatives containing 1,3,4-oxadiazole-2-thiol moiety. Org. Chem, 2013, 2013, 1-8.
[239]
Kilcigil, G.A.; Kus, C.; Coban, T.; Ozdamar, E.D.; Eke, B.C. Identification of a novel series of N-Phenyl-5-[(2-phenylbenzimidazol-1-yl)methyl]-1,3,4-oxadiazol-2-amines as potent antioxidants and radical scavengers. Arch. Pharm. Chem. Life Sci, 2014, 347(4), 276-282.
[240]
Basha, N.M.; Seenaiah, D.; Padmaja, A.; Padmavathi, V.; Bhargav, D.S.; Vijaya, T. Synthesis and antioxidant activity of bis and tris heterocycles. Arch. Pharm. Chem. Life Sci, 2014, 347(1), 54-67.
[241]
Al-Ayed, A.S.; Hamdi, N. A new and efficient method for the synthesis of novel 3-acetyl coumarins oxadiazoles derivatives with expected biological activity. Molecules, 2014, 19(1), 911-924.
[242]
Shakir, R.M.; Ariffin, A.; Abdulla, M.A. Synthesis of new 2,5-di-substituted 1,3,4-oxadiazoles bearing 2,6-di-tert-butylphenol moieties and evaluation of their antioxidant activity. Molecules, 2014, 19(3), 3436-3449.
[243]
Patrao, P.; Khader, A.M.A.; Kalluraya, B. Vinayachandra. Synthesis of new 5-naphthyl substituted 1,3,4-oxadiazole derivatives and their antioxidant activity. Der Pharma Chem., 2013, 5(2), 24-32.
[244]
Ali, K.F. Synthesis and antioxidant ability of 5-amino-1,3,4-oxadiazole derivatives containing 2,6-dimethoxyphenol. Orient. J. Chem., 2015, 31(1), 239-247.
[245]
Cihan-Ustundag, G.; Gursoy, E.; Naesens, L.; Ulusoy-Guzeldemirci, N.; Capan, G. Synthesis and antiviral properties of novel indole-based thiosemicarbazides and 4-thiazolidinones. Bioorg. Med. Chem., 2016, 24(2), 240-246.
[246]
Dawood, K.M.; Eldebss, T.M.A.; El-Zahabi, H.S.A.; Yousef, M.H. Synthesis and antiviral activity of some new bis-1,3-thiazole derivatives. Eur. J. Med. Chem., 2015, 102, 266-276.
[247]
Zhong, Z.J.; Zhang, D.J.; Peng, Z.G.; Li, Y.H.; Shan, G.Z.; Zuo, L.M.; Wu, L.T.; Li, S.Y.; Gao, R.M.; Li, Z.R. Synthesis and antiviral activity of a novel class of (5-oxazolyl)phenyl amines. Eur. J. Med. Chem., 2013, 69, 32-43.
[248]
Glowacka, I.E.; Balzarini, J.; Wroblewski, A.E. The synthesis, antiviral, cytostatic and cytotoxic evaluation of a new series of acyclonucleotide analogues with a 1,2,3-triazole linker. Eur. J. Med. Chem., 2013, 70, 703-722.
[249]
Xu, W.M.; Li, S.Z.; He, M.; Yang, S.; Li, X.Y.; Li, P. Synthesis and bioactivities of novel thioether/sulfone derivatives containing 1,2,3-thiadiazole and 1,3,4-oxadiazole/thiadiazole moiety. Bioorg. Med. Chem. Lett., 2013, 23(21), 5821-5824.
[250]
Lai, H.; Dou, D.; Aravapalli, S.; Teramoto, T.; Lushington, G.H.; Mwania, T.M.; Alliston, K.R.; Eichhorn, D.M.; Padmanabhan, R.; Groutas, W.C. Design, synthesis and characterization of novel 1,2-Benzisothiazol-3(2H)-one and 1,3,4-oxadiazole hybrid derivatives: potent inhibitors of Dengue and West Nile Virus NS2B/NS3 proteases. Bioorg. Med. Chem., 2013, 21(1), 102-113.
[251]
Walji, A.M.; Sanchez, R.I.; Clas, S.D. ’ Nofsinger, R.; Ruiz, M.D.L.; Li, J.; Bennet, A.; John, C.; Bennett, D.J.; Sanders, J.M.; Marco, C.N.D.; Kim, S.H.; Balsells, J.; Ceglia, S.C.; Dang, Q.; Manser, K.; Nissley, B.; Wai, J.S.; Hafey, M.; Wang, J.; Chessen, G.; Templeton, A.; Higgins, J.; Smith, R.; Wu, Y.; Grobler, J.; Coleman, P.J. Discovery of MK-8970: An acetal carbonate prodrug of Raltegravir with enhanced colonic absorption. ChemMedChem, 2015, 10(2), 245-252.
[252]
Wu, W.; Chen, Q.; Tai, A.; Jiang, G.; Ouyang, G. Synthesis and antiviral activity of 2-substituted methylthio-5-(4-amino-2-methylpyrimidin-5-yl)-1,3,4-oxadiazole derivatives. Bioorg. Med. Chem. Lett., 2015, 25(10), 2243-2246.
[253]
Gan, X.; Hu, D.; Li, P.; Wu, J.; Chen, X.; Xue, W.; Song, B. Design, synthesis, antiviral activity and three-dimensional quantitative structure-activity relationship study of novel 1,4-pentadien-3-one derivatives containing the 1,3,4-oxadiazole moiety. Pest Manag. Sci., 2016, 72(3), 534-543.
[254]
Benmansour, F.; Eydoux, C.; Querat, G.; de Lamballerie, X.; Canrad, B.; Alvarez, K.; Guillemot, J.C.; Barral, K. Novel 2-phenyl-5-[(E)-2-(thiophen-2-yl)ethenyl]-1,3,4-oxadiazole and 3-phenyl-5-[(E)-2-(thiophen-2-yl)ethenyl]-1,2,4-oxadiazole derivatives as dengue virus inhibitors targeting NS5 polymerase. Eur. J. Med. Chem., 2016, 109, 146-156.
[255]
Goodman, G.R.; Epstein, S. Mechanisms of immunosuppressant-induced bone disease. Adv. Org. Biol, 1998, 5, 739-763.
[256]
Fernandez, O. Combination therapy in multiple sclerosis. J. Neurol. Sci., 2007, 259, 95-103.
[257]
Sindhi, R.; Magill, A.; Manavalan, S.; Yost, M.; Haluscczyak, C.; Zeevi, A. Peripheral lymphocyte markers as surrogate measures of immunosuppression and post-transplant clinical states. Clin. Appl. Immunol. Rev., 2004, 4(4), 225-228.
[258]
Sun, J.; Cao, N.; Zhang, X.M.; Yang, Y.S.; Zhang, Y.B.; Wang, X.M.; Zhu, H.L. Oxadiazole derivatives containing 1,4-benzodioxan as potential immunosuppressive agents against RAW264.7 cells. Bioorg. Med. Chem., 2011, 19, 4895-4902.
[259]
Zhang, Z.M.; Zhang, X.W.; Zhao, Z.Z.; Yan, R.; Xu, R.; Gong, H.B.; Zhu, H.L. Synthesis, biological evaluation and molecular docking studies of 1,3,4-oxadiazole derivatives as potential immunosuppressive agents. Bioorg. Med. Chem., 2012, 20(10), 3359-3367.
[260]
Tang, J.F.; Lv, X.H.; Wang, X.L.; Sun, J.; Zhang, Y.B.; Yang, Y.S.; Gong, H.B.; Zhu, H.L. Design, synthesis, biological evaluation and molecular modeling of novel 1,3,4-oxadiazole derivatives based on Vanillic acid as potential immunosuppressive agents. Bioorg. Med. Chem., 2012, 20(14), 4226-4236.
[261]
Pisani, L.; Farina, R.; Nicolotti, O.; Gadaleta, D.; Otero, R.S.; Catto, M.; Braccio, M.D.; Alvarez, E.M.; Carotti, A. In silico design of novel 2H-chromen-2-one derivatives as potent and selective MAO-B inhibitors. Eur. J. Med. Chem., 2015, 89, 98-105.
[262]
Rojas, R.J.; Edmondson, D.E.; Almos, T.; Scott, R.; Massari, M.E. Reversible and irreversible small molecule inhibitors of monoamine oxidase B (MAO-B) investigated by biophysical techniques. Bioorg. Med. Chem., 2015, 23(4), 770-778.
[263]
Sahoo, A.; Yabanoglu, S.; Sinha, B.N.; Ucar, G.; Basu, A.; Jayaprakash, V. Towards development of selective and reversible pyrazoline based MAO-inhibitors: synthesis, biological evaluation and docking studies. Bioorg. Med. Chem. Lett., 2010, 20(1), 132-136.
[264]
Maccioni, E.; Alcaro, S.; Cirilli, R.; Vigo, S.; Cardia, M.C.; Sanna, M.L.; Meleddu, R.; Yanez, M.; Costa, G.; Casu, L.; Matyus, P.; Distinto, S. 3-Acetyl-2,5-diaryl-2,3-dihydro-1,3,4-oxadiazoles: A new scaffold for the selective inhibition of monoamine oxidase B. J. Med. Chem., 2011, 54(18), 6394-6398.
[265]
Biglar, M.; Soltani, K.; Nabati, F.; Bazl, R.; Mojab, F.; Amanlou, M. A preliminary investigation of the Jack-Bean urease inhibition by randomly selected traditionally used medicines. Iran. J. Pharm. Res., 2012, 11(3), 831-837.
[266]
Amtul, Z.; Rahman, A.U.; Siddiqui, R.A.; Choudhary, M.I. Chemistry and mechanism of urease inhibition. Curr. Med. Chem., 2002, 9(14), 1323-1348.
[267]
Hanif, M.; Shoaib, K.; Saleem, M.; Rama, N.H.; Zaib, S.; Iqbal, J. Synthesis, urease inhibition, antioxidant, antibacterial, and molecular docking studies of 1,3,4-oxadiazole derivatives. ISRN Pharmacol., 2012, 2012, 1-9.
[268]
Akhtar, T.; Khan, M.A.; Iqbal, J.; Jones, P.G.; Hameed, S. A facile one pot synthesis of 2-arylamino-5-aryloxyalkyl-1,3,4-oxadiazoles and their urease inhibition studies. Chem. Biol. Drug Des., 2014, 84(1), 92-98.
[269]
Siddiqui, S.M.; Salahuddin, A.; Azam, A. Mannich base derivatives of 1,3,4-oxadiazole: synthesis and screening against Entamoeba histolytica. Med. Chem. Res., 2013, 22(3), 1313-1319.
[270]
Chen, Y.; Xu, X.; Liu, X.; Yu, M.; Liu, B.F.; Zhang, G. Synthesis and evaluation of a series of 2-substituted-5-Thiopropylpiperazine (Piperidine)-1,3,4-oxadiazoles derivatives as atypical antipsychotics. PLoS One, 2012, 7, 1-10.
[271]
Leonczak, P.; Gao, L.J.; Ramadori, A.T.; Lescrinier, E.; Rozenski, J.; Jonghe, S.D.; Herdewijn, P. Synthesis and structure–activity relationship studies of 2-(1,3,4-oxadiazole-2(3H)-thione)-3-amino-5-arylthieno[2,3-b]pyridines as inhibitors of DRAK2. ChemMedChem, 2014, 9(11), 2587-2601.
[272]
Zawawi, N.K.N.A.; Taha, M.; Ahmat, N.; Wadood, A.; Ismail, N.H.; Rahim, F.; Ali, M.; Abdullah, N.; Khan, K.M. Novel 2,5-disubtituted-1,3,4-oxadiazoles with benzimidazole backbone: A new class of β-glucuronidase inhibitors and in silico studies. Bioorg. Med. Chem., 2015, 23(13), 3119-3125.
[273]
Taha, M.; Ismail, N.H.; Imran, S.; Selvaraj, M.; Rahim, A.; Ali, M.; Siddiqui, S.; Rahim, F.; Khan, K.M. Synthesis of novel benzohydrazone–oxadiazole hybrids as β-glucuronidase inhibitors and molecular modeling studies. Bioorg. Med. Chem., 2015, 23(23), 7394-7404.
[274]
Ashry, E.S.H.E.; Tamany, E.S.H.E.; Fattah, M.E.D.A.E.; Aly, M.R.E.; Boraei, A.T.A.; Mesaik, M.A.; Abdalla, O.M.; Fatima, B.; Jabeen, A.; Shukrulla, A.; Soomro, S. Immunomodulatory properties of S- and N-alkylated 5-(1H-indol-2-yl)-1,3,4-oxadiazole-2(3H)-thione. J. Enzyme Inhib. Med. Chem., 2013, 28(1), 105-112.
[275]
Zuo, Y.; Yang, S.G.; Jiang, L.L.; Hao, G.F.; Wang, Z.F.; Wu, Q.Y.; Xi, Z.; Yang, G.F. Quantitative structure–activity relationships of 1,3,4-thiadiazol-2(3H)-ones and 1,3,4-oxadiazol-2(3H)-ones as human protoporphyrinogen oxidase inhibitors. Bioorg. Med. Chem., 2012, 20(1), 296-304.
[276]
Sadek, M.M.E.; Hassan, S.Y.; Abdelwahab, H.E.; Yacout, G.A. Synthesis and bioassay of a new class of furanyl-1,3,4-oxadiazole derivatives. Molecules, 2013, 18(7), 8550-8562.

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