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Mini-Reviews in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-193X
ISSN (Online): 1875-6298

Mini-Review Article

A Comprehensive Review on Synthetic Approaches and Biological Activities of 1,3,4-oxadiazole

Author(s): Sunita Kumari, Rajnish Kumar*, Avijit Mazumder, Salahuddin, Shivani Saxena, Divya Sharma and Sagar Joshi

Volume 19, Issue 8, 2022

Published on: 28 March, 2022

Page: [906 - 919] Pages: 14

DOI: 10.2174/1570193X19666220112151214

Price: $65

Abstract

Among the large variety of nitrogen and oxygen heterocycles, 1,3,4-oxadiazole scaffold has attracted considerable attention owing to its ability to perform an extensive range of pharmacological actions. Therefore, significant efforts of organic chemists have been directed towards the construction of new drug candidates containing 1,3,4-oxadiazole subunits connected to a known pharmaceutical or a potential pharmacophore. This paper highlights recent publications on the various synthesis techniques of 1,3,4-oxadiazole and related compounds over the previous ten years (2011–2021). The purpose of this review is to present several ways for synthesizing oxadiazole. These heterocyclics are formed mainly by the cyclization reactions of various reactants under diverse conditions. A high priority is given to these heterocyclics in literature investigations due to their pharmacological significance, such as their anticonvulsant, anticancer, antioxidant, antiinflammatory, antibacterial, antidiabetic activities, etc.

Keywords: Heterocycles, 1, 3, 4-oxadiazole, pharmacological actions, synthesis, anticancer, heterocyclic chemistry.

Graphical Abstract

[1]
Katritzky, A.R.; Ramsden, C.A.; Joule, J.A.; Zhdankin, V.V. Handbook of heterocyclic chemistry; Elsevier, 2010.
[2]
Sadek, B.; Fahelelbom, K.M. Synthesis, characterization, and antimicrobial evaluation of oxadiazole congeners. Molecules, 2011, 16(6), 4339-4347.
[http://dx.doi.org/10.3390/molecules16064339] [PMID: 21613975]
[3]
Hemming, K. Recent developments in the synthesis, chemistry and applications of the fully unsaturated 1, 2, 4-oxadiazoles. J. Chem. Res., 2001, 2001(6), 209-216.
[http://dx.doi.org/10.3184/030823401103169603]
[4]
Pitasse-Santos, P.; Sueth-Santiago, V.; Lima, M.E. 1, 2, 4-and 1, 3, 4-Oxadiazoles as scaffolds in the development of antiparasitic agents. J. Braz. Chem. Soc., 2018, 29(3), 435-456.
[5]
Nagaraj, C.K.; Niranjan, M.S.; Kiran, S. 1, 3, 4-Oxadiazole: A potent drug candidate with various pharmacological activities. Int. J. Pharm. Pharm. Sci., 2011, 3(3), 9-16.
[6]
Boström, J.; Hogner, A.; Llinàs, A.; Wellner, E.; Plowright, A.T. Oxadiazoles in medicinal chemistry. J. Med. Chem., 2012, 55(5), 1817-1830.
[http://dx.doi.org/10.1021/jm2013248] [PMID: 22185670]
[7]
Chitambar, C.R.; Wereley, J.P. Resistance to the antitumor agent gallium nitrate in human leukemic cells is associated with decreased gallium/iron uptake, increased activity of iron regulatory protein-1, and decreased ferritin production. J. Biol. Chem., 1997, 272(18), 12151-12157.
[http://dx.doi.org/10.1074/jbc.272.18.12151] [PMID: 9115286]
[8]
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(1), 8.
[http://dx.doi.org/10.1186/2191-2858-2-8] [PMID: 22380426]
[9]
Bala, S.; Kamboj, S.; Kumar, A. Heterocyclic 1, 3, 4-oxadiazole compounds with diverse biological activities: A comprehensive review. J. Pharm. Res., 2010, 3(12), 2993-2997.
[10]
Singh, P.; Jangra, P.K. Oxadiazoles: a novel class of anti-convulsant agents. Der Chemica Sinica., 2010, 1(3), 118-123.
[11]
Singh, A.K.; Sahu, V.K.; Yadav, D. Biological activities of 2, 5-di-substituted-1, 3, 4-oxadiazoles. Int. J. Pharm. Sci. Res., 2011, 2(6), 135-147.
[12]
Nimavat, B.; Mohan, S.; Saravanan, J.; Deka, S.; Talukdar, A.; Sahariah, B.J.; Dey, B.K.; Sharma, 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.
[13]
Ali, M.A.; Shaharyar, M. Oxadiazole mannich bases: synthesis and antimycobacterial activity. Bioorg. Med. Chem. Lett., 2007, 17(12), 3314-3316.
[http://dx.doi.org/10.1016/j.bmcl.2007.04.004] [PMID: 17467984]
[14]
Yar, M.S.; Siddiqui, A.A.; Ashraf Ali, M. Synthesis and anti tuberculostatic activity of Novel 1, 3, 4-Oxadiazole derivatives. J. Chin. Chem. Soc. (Taipei), 2007, 54(1), 5-8.
[http://dx.doi.org/10.1002/jccs.200700002]
[15]
Kumar, H.; Javed, S.A.; Khan, S.A.; Amir, M. 1,3,4-Oxadiazole/thiadiazole and 1,2,4-triazole derivatives of biphenyl-4-yloxy acetic acid: Synthesis and preliminary evaluation of biological properties. Eur. J. Med. Chem., 2008, 43(12), 2688-2698.
[http://dx.doi.org/10.1016/j.ejmech.2008.01.039] [PMID: 18395299]
[16]
Salahuddin, M.A.; Yar, M.S.; Mazumder, R.; Chakraborthy, G.S.; Ahsan, M.J.; Rahman, M.U. Updates on synthesis and biological activities of 1, 3, 4-oxadiazole: a review. Synth. Commun., 2017, 47(20), 1805-1847.
[http://dx.doi.org/10.1080/00397911.2017.1360911]
[17]
Khalilullah, H.; J Ahsan, M; Hedaitullah, M; Khan, S; Ahmed, B. 1, 3, 4-oxadiazole: a biologically active scaffold. Mini Rev. Med. Chem., 2012, 12(8), 789-801.
[http://dx.doi.org/10.2174/138955712801264800] [PMID: 22512560]
[18]
Sharma, S.; Sharma, P.K.; Kumar, N.; Dudhe, R. A review: oxadiazole their chemistry and pharmacological potentials. Pharma Chem., 2010, 2(4), 253-263.
[19]
Guimarães, C.R.; Boger, D.L.; Jorgensen, W.L. Elucidation of fatty acid amide hydrolase inhibition by potent α-ketoheterocycle derivatives from Monte Carlo simulations. J. Am. Chem. Soc., 2005, 127(49), 17377-17384.
[http://dx.doi.org/10.1021/ja055438j] [PMID: 16332087]
[20]
Summers, L.A. The bipyridines. Adv. Heterocycl. Chem., 1984, 35, 281-374.
[http://dx.doi.org/10.1016/S0065-2725(08)60151-8]
[21]
Johns, B.A.; Weatherhead, J.G.; Allen, S.H.; Thompson, J.B.; Garvey, E.P.; Foster, S.A.; Jeffrey, J.L.; Miller, W.H. 1,3,4-Oxadiazole substituted naphthyridines as HIV-1 integrase inhibitors. Part 2: SAR of the C5 position. Bioorg. Med. Chem. Lett., 2009, 19(6), 1807-1810.
[http://dx.doi.org/10.1016/j.bmcl.2009.01.089] [PMID: 19217284]
[22]
Llinàs-Brunet, M.; Bailey, M.D.; Bolger, G.; Brochu, C.; Faucher, A.M.; Ferland, J.M.; Garneau, M.; Ghiro, E.; Gorys, V.; Grand-Maître, C.; Halmos, T.; Lapeyre-Paquette, N.; Liard, F.; Poirier, M.; Rhéaume, M.; Tsantrizos, Y.S.; Lamarre, D. Structure-activity study on a novel series of macrocyclic inhibitors of the hepatitis C virus NS3 protease leading to the discovery of BILN 2061. J. Med. Chem., 2004, 47(7), 1605-1608.
[http://dx.doi.org/10.1021/jm0342414] [PMID: 15027850]
[23]
Lee, L.; Robb, L.M.; Lee, M.; Davis, R.; Mackay, H.; Chavda, S.; Babu, B.; O’Brien, E.L.; Risinger, A.L.; Mooberry, S.L.; Lee, M. Design, synthesis, and biological evaluations of 2,5-diaryl-2,3-dihydro-1,3,4-oxadiazoline analogs of combretastatin-A4. J. Med. Chem., 2010, 53(1), 325-334.
[http://dx.doi.org/10.1021/jm901268n] [PMID: 19894742]
[24]
Kiselyov, A.S.; Semenova, M.N.; Chernyshova, N.B.; Leitao, A.; Samet, A.V.; Kislyi, K.A.; Raihstat, M.M.; Oprea, T.; Lemcke, H.; Lantow, M.; Weiss, D.G.; Ikizalp, N.N.; Kuznetsov, S.A.; Semenov, V.V. Novel derivatives of 1,3,4-oxadiazoles are potent mitostatic agents featuring strong microtubule depolymerizing activity in the sea urchin embryo and cell culture assays. Eur. J. Med. Chem., 2010, 45(5), 1683-1697.
[http://dx.doi.org/10.1016/j.ejmech.2009.12.072] [PMID: 20110137]
[25]
Zarghi, A.; Hajimahdi, Z.; Mohebbi, S.; Rashidi, H.; Mozaffari, S.; Sarraf, S.; Faizi, M.; Tabatabaee, S.A.; Shafiee, A. Design and synthesis of new 2-substituted-5-[2-(2-halobenzyloxy)phenyl]-1,3,4-oxadiazoles as anticonvulsant agents. Chem. Pharm. Bull. (Tokyo), 2008, 56(4), 509-512.
[http://dx.doi.org/10.1248/cpb.56.509] [PMID: 18379099]
[26]
Zarghi, A.; Tabatabai, S.A.; Faizi, M.; Ahadian, A.; Navabi, P.; Zanganeh, 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.
[http://dx.doi.org/10.1016/j.bmcl.2005.02.014] [PMID: 15780622]
[27]
Jayashankar, B.; Lokanath Rai, K.M.; Baskaran, N.; Sathish, H.S. Synthesis and pharmacological evaluation of 1,3,4-oxadiazole bearing bis(heterocycle) derivatives as anti-inflammatory and analgesic agents. Eur. J. Med. Chem., 2009, 44(10), 3898-3902.
[http://dx.doi.org/10.1016/j.ejmech.2009.04.006] [PMID: 19423197]
[28]
Ghani, U.; Ullah, N. New potent inhibitors of tyrosinase: novel clues to binding of 1,3,4-thiadiazole-2(3H)-thiones, 1,3,4-oxadiazole-2(3H)-thiones, 4-amino-1,2,4-triazole-5(4H)-thiones, and substituted hydrazides to the dicopper active site. Bioorg. Med. Chem., 2010, 18(11), 4042-4048.
[http://dx.doi.org/10.1016/j.bmc.2010.04.021] [PMID: 20452224]
[29]
Bankar, G.R.; Nandakumar, K.; Nayak, P.G.; Thakur, A.; Chamallamudi, M.R.; Nampurath, G.K. Vasorelaxant effect in rat aortic rings through calcium channel blockage: a preliminary in vitro assessment of a 1,3,4-oxadiazole derivative. Chem. Biol. Interact., 2009, 181(3), 377-382.
[http://dx.doi.org/10.1016/j.cbi.2009.07.014] [PMID: 19643099]
[30]
Mohammed Iqbal, A.K.; Khan, A.Y.; Kalashetti, M.B.; Belavagi, N.S.; Gong, Y.D.; Khazi, I.A. Synthesis, hypoglycemic and hypolipidemic activities of novel thiazolidinedione derivatives containing thiazole/triazole/oxadiazole ring. Eur. J. Med. Chem., 2012, 53, 308-315.
[http://dx.doi.org/10.1016/j.ejmech.2012.04.015] [PMID: 22575535]
[31]
Schiefer, I.T.; VandeVrede, L.; Fa’, M.; Arancio, O.; Thatcher, G.R. Furoxans (1,2,5-oxadiazole-N-oxides) as novel NO mimetic neuroprotective and procognitive agents. J. Med. Chem., 2012, 55(7), 3076-3087.
[http://dx.doi.org/10.1021/jm201504s] [PMID: 22429006]
[32]
Warrener, R.N. New adventures in the synthesis of hetero-bridged syn-facially fused norbornadienes (“[n] polynorbornadienes”) and their topological diversity. Eur. J. Org. Chem., 2000, 2000(20), 3363-3380.
[http://dx.doi.org/10.1002/1099-0690(200010)2000:20<3363:AID-EJOC3363>3.0.CO;2-I]
[33]
Savarino, A. A historical sketch of the discovery and development of HIV-1 integrase inhibitors. Expert Opin. Investig. Drugs, 2006, 15(12), 1507-1522.
[http://dx.doi.org/10.1517/13543784.15.12.1507] [PMID: 17107277]
[34]
James, N.D.; Growcott, J.W. Zibotentan endothelin ETA receptor antagonist oncolytic. Drugs Future, 2009, 34(8), 624-633.
[35]
Brandenberger, H.; Maes, R.A., Eds.; Analytical toxicology for clinical, forensic and pharmaceutical chemists; Walter de Gruyter, 2011.
[36]
Ducharme, Y.; Blouin, M.; Brideau, C.; Châteauneuf, A.; Gareau, Y.; Grimm, E.L.; Juteau, H.; Laliberté, S.; MacKay, B.; Massé, F.; Ouellet, M.; Salem, M.; Styhler, A.; Friesen, R.W. The discovery of setileuton, a potent and selective 5-lipoxygenase inhibitor. ACS Med. Chem. Lett., 2010, 1(4), 170-174.
[http://dx.doi.org/10.1021/ml100029k] [PMID: 24900191]
[37]
Adelstein, G.W.; Yen, C.H.; Dajani, E.Z.; Bianchi, R.G. 3,3-Diphenyl-3-(2-alkyl-1,3,4-oxadiazol-5-yl)propylcycloalkylamines, a novel series of antidiarrheal agents. J. Med. Chem., 1976, 19(10), 1221-1225.
[http://dx.doi.org/10.1021/jm00232a010] [PMID: 994153]
[38]
Ouyang, X.; Piatnitski, E.L.; Pattaropong, V.; Chen, X.; He, H.Y.; Kiselyov, A.S.; Velankar, A.; Kawakami, J.; Labelle, M.; Smith, L.I.I.; Lohman, J.; Lee, S.P.; Malikzay, A.; Fleming, J.; Gerlak, J.; Wang, Y.; Rosler, R.L.; Zhou, K.; Mitelman, S.; Camara, M.; Surguladze, D.; Doody, J.F.; Tuma, M.C. Oxadiazole derivatives as a novel class of antimitotic agents: Synthesis, inhibition of tubulin polymerization, and activity in tumor cell lines. Bioorg. Med. Chem. Lett., 2006, 16(5), 1191-1196.
[http://dx.doi.org/10.1016/j.bmcl.2005.11.094] [PMID: 16377187]
[39]
Patel, K.D.; Prajapati, S.M.; Panchal, S.N.; Patel, H.D. Review of synthesis of 1, 3, 4-oxadiazole derivatives. Synth. Commun., 2014, 44(13), 1859-1875.
[http://dx.doi.org/10.1080/00397911.2013.879901]
[40]
Ogata, M.; Atobe, H.; Kushida, H.; Yamamoto, K. In vitro sensitivity of mycoplasmas isolated from various animals and sewage to antibiotics and nitrofurans. J. Antibiot. (Tokyo), 1971, 24(7), 443-451.
[http://dx.doi.org/10.7164/antibiotics.24.443] [PMID: 4327309]
[41]
de Oliveira, C.S.; Lira, B.F.; Barbosa-Filho, J.M.; Lorenzo, J.G.; de Athayde-Filho, P.F.; Filgueiras, P. Synthetic approaches and pharmacological activity of 1,3,4-oxadiazoles: a review of the literature from 2000-2012. Molecules, 2012, 17(9), 10192-10231.
[http://dx.doi.org/10.3390/molecules170910192] [PMID: 22926303]
[42]
KumaráRout S. A one pot synthesis of [1, 3, 4]-oxadiazoles mediated by molecular iodine. RSC Advances, 2012, 2(8), 3180-3183.
[http://dx.doi.org/10.1039/c2ra00044j]
[43]
Wan, Z.K.; Ousman, E.F.; Papaioannou, N.; Saiah, E. Phosphonium-mediated cyclization of N-(2-aminophenyl) thioureas: efficient synthesis of 2-aminobenzimidazoles. Tetrahedron Lett., 2011, 52(32), 4149-4152.
[http://dx.doi.org/10.1016/j.tetlet.2011.05.146]
[44]
Chaudhari, P.S.; Pathare, S.P.; Akamanchi, K.G. o-Iodoxybenzoic acid mediated oxidative desulfurization initiated domino reactions for synthesis of azoles. J. Org. Chem., 2012, 77(8), 3716-3723.
[http://dx.doi.org/10.1021/jo2025509] [PMID: 22423599]
[45]
Coppo, F.T.; Evans, K.A.; Graybill, T.L.; Burton, G. Efficient one-pot preparation of 5-substituted-2-amino-1, 3, 4-oxadiazoles using resin-bound reagents. Tetrahedron Lett., 2004, 45(16), 3257-3260.
[http://dx.doi.org/10.1016/j.tetlet.2004.02.119]
[46]
Maghari, S.; Ramezanpour, S.; Darvish, F.; Balalaie, S.; Rominger, F.; Bijanzadeh, H.R. A new and efficient synthesis of 1, 3, 4-oxadiazole derivatives using TBTU. Tetrahedron, 2013, 69(8), 2075-2080.
[http://dx.doi.org/10.1016/j.tet.2012.11.071]
[47]
Dolman, S.J.; Gosselin, F.; O’Shea, P.D.; Davies, I.W. Superior reactivity of thiosemicarbazides in the synthesis of 2-amino-1,3,4-oxadiazoles. J. Org. Chem., 2006, 71(25), 9548-9551.
[http://dx.doi.org/10.1021/jo0618730] [PMID: 17137395]
[48]
Yang, S.J.; Lee, S.H.; Kwak, H.J.; Gong, Y.D. Regioselective synthesis of 2-amino-substituted 1,3,4-oxadiazole and 1,3,4-thiadiazole derivativesvia reagent-based cyclization of thiosemicarbazide intermediate. J. Org. Chem., 2013, 78(2), 438-444.
[http://dx.doi.org/10.1021/jo302324r] [PMID: 23215154]
[49]
Chekler, E.L.; Elokdah, H.M.; Butera, J. Efficient one-pot synthesis of substituted 2-amino-1, 3, 4-oxadiazoles. Tetrahedron Lett., 2008, 49(47), 6709-6711.
[http://dx.doi.org/10.1016/j.tetlet.2008.09.057]
[50]
Xie, Y.; Liu, J.; Yang, P.; Shi, X.; Li, J. Synthesis of 2-amino-1, 3, 4-oxadiazoles from isoselenocyanates via cyclodeselenization. Tetrahedron, 2011, 67(30), 5369-5374.
[http://dx.doi.org/10.1016/j.tet.2011.05.100]
[51]
Rajak, H.; Kharya, M.D.; Mishra, P. Synthesis and local anesthetic activity of some novel N-[5-(4-substituted)phenyl-1,3,4-oxadiazol-2-yl]-2-(substituted)-acetamides. Arch. Pharm. (Weinheim), 2008, 341(4), 247-261.
[http://dx.doi.org/10.1002/ardp.200700146] [PMID: 18293435]
[52]
Rivera, N.R.; Balsells, J.; Hansen, K.B. Synthesis of 2-amino-5-substituted-1, 3, 4-oxadiazoles using 1, 3-dibromo-5, 5-dimethylhydantoin as oxidant. Tetrahedron Lett., 2006, 47(28), 4889-4891.
[http://dx.doi.org/10.1016/j.tetlet.2006.05.033]
[53]
Dobrotă C.; Paraschivescu, C.C.; Dumitru, I.; Matache, M.; Baciu, I.; Ruţă, L.L. Convenient preparation of unsymmetrical 2, 5-disubstituted 1, 3, 4-oxadiazoles promoted by Dess–Martin reagent. Tetrahedron Lett., 2009, 50(17), 1886-1888.
[http://dx.doi.org/10.1016/j.tetlet.2009.02.054]
[54]
Pardeshi, S.P.; Patil, S.S.; Bobade, V.D. N-Chlorosuccinimide/1, 8-Diazabicyclo [5.4. 0] undec-7-ene (DBU)–Mediated Synthesis of 2, 5-Disubstituted 1, 3, 4-Oxadiazoles. Synth. Commun., 2010, 40(11), 1601-1606.
[http://dx.doi.org/10.1080/00397910903134592]
[55]
Gao, P.; Wei, Y. Efficient oxidative cyclization of N-acylhydrazones for the synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles using t-BuOI under neutral conditions. Heterocycl. Commun., 2013, 19(2), 113-119.
[http://dx.doi.org/10.1515/hc-2012-0179]
[56]
Prakash, O.; Kumar, M.; Kumar, R.; Sharma, C.; Aneja, K.R. Hypervalent iodine(III) mediated synthesis of novel unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles as antibacterial and antifungal agents. Eur. J. Med. Chem., 2010, 45(9), 4252-4257.
[http://dx.doi.org/10.1016/j.ejmech.2010.06.023] [PMID: 20630627]
[57]
Abdu Musad, E.; Mohamed, R.; Saeed, B.A.; Vishwanath, B.S.; Rai, K.M. Synthesis and evaluation of antioxidant and antibacterial activities of new substituted bis(1,3,4-oxadiazoles), 3,5-bis(substituted) pyrazoles and isoxazoles. Bioorg. Med. Chem. Lett., 2011, 21(12), 3536-3540.
[http://dx.doi.org/10.1016/j.bmcl.2011.04.142] [PMID: 21612921]
[58]
Al-Ghorbani, M.; Gouda, M.A.; Baashen, M. A review on synthetic routes of 5-aryl-1, 3, 4-oxadiazoles. Indian J. Heterocycl. Chem., 2019, 29(1), 27-37.
[59]
Guin, S.; Ghosh, T.; Rout, S.K.; Banerjee, A.; Patel, B.K. Cu(II) catalyzed imine C-H functionalization leading to synthesis of 2,5-substituted 1,3,4-oxadiazoles. Org. Lett., 2011, 13(22), 5976-5979.
[http://dx.doi.org/10.1021/ol202409r] [PMID: 22007797]
[60]
Cui, Z.N.; Shi, Y.X.; Zhang, L.; Ling, Y.; Li, B.J.; Nishida, Y.; Yang, X.L. Synthesis and fungicidal activity of novel 2,5-disubstituted-1,3,4-oxadiazole derivatives. J. Agric. Food Chem., 2012, 60(47), 11649-11656.
[http://dx.doi.org/10.1021/jf303807a] [PMID: 23134289]
[61]
Paraschivescu, C.C.; Matache, M. Dobrotă C.; Nicolescu, A.; Maxim, C.; Deleanu, C.; Fărcăşanu, I.C.; Hădade, N.D. Unexpected formation of N-(1-(2-aryl-hydrazono)isoindolin-2-yl)benzamides and their conversion into 1,2-(bis-1,3,4-oxadiazol-2-yl)benzenes. J. Org. Chem., 2013, 78(6), 2670-2679.
[http://dx.doi.org/10.1021/jo400023z] [PMID: 23394598]
[62]
Dabiri, M.; Salehi, P.; Baghbanzadeh, M.; Bahramnejad, M. A facile procedure for the one-pot synthesis of unsymmetrical 2, 5-disubstituted 1, 3, 4-oxadiazoles. Tetrahedron Lett., 2006, 47(39), 6983-6986.
[http://dx.doi.org/10.1016/j.tetlet.2006.07.127]
[63]
Pore, D.M.; Mahadik, S.M.; Desai, U.V. Trichloroisocyanuric acid–mediated one-pot synthesis of unsymmetrical 2, 5-disubstituted 1, 3, 4-oxadiazoles at ambient temperature. Synth. Commun., 2008, 38(18), 3121-3128.
[http://dx.doi.org/10.1080/00397910802054289]
[64]
Sangshetti, J.N.; Dharmadhikari, P.P.; Chouthe, R.S.; Fatema, B.; Lad, V.; Karande, V.; Darandale, S.N.; Shinde, D.B. Microwave assisted nano (ZnO-TiO2) catalyzed synthesis of some new 4,5,6,7-tetrahydro-6-((5-substituted-1,3,4-oxadiazol-2-yl)methyl)thieno[2,3-c]pyridine as antimicrobial agents. Bioorg. Med. Chem. Lett., 2013, 23(7), 2250-2253.
[http://dx.doi.org/10.1016/j.bmcl.2013.01.041] [PMID: 23434418]
[65]
Brockmeyer, F.; van Gerven, D.; Saak, W.; Martens, J. Two sequential multicomponent reactions: synthesis of thiazolidin-4-yl-1, 3, 4-oxadiazoles under mild conditions. Synthesis, 2014, 46(12), 1603-1612.
[http://dx.doi.org/10.1055/s-0033-1341043]
[66]
Sharma, L.K.; Kumar, S.; Singh, S.; Singh, R.K. Electrochemical synthesis of 5-substituted-2-amino (substituted amino)-1, 3, 4-oxadiazoles at the platinum electrode. Russ. J. Electrochem., 2010, 46(1), 34-40.
[http://dx.doi.org/10.1134/S1023193510010040]
[67]
Lotfi, B; Mustafa, B; Leila, L; Salima, M. Electrocyclization of semicarbazone; A novel route of green synthesis of 2, 5- disubstituted-1, 3, 4-oxadiazoles. Int. J. Electrochem. Sci., 2011, 6(1991), 2000.
[68]
Ma, H.Y.; Zha, Z.G.; Zhang, Z.L.; Meng, L.; Wang, Z.Y. Electrosynthesis of oxadiazoles from benzoylhydrazines. Chin. Chem. Lett., 2013, 24(9), 780-782.
[http://dx.doi.org/10.1016/j.cclet.2013.05.032]
[69]
Stabile, P.; Lamonica, A.; Ribecai, A.; Castoldi, D.; Guercio, G.; Curcuruto, O. Mild and convenient one-pot synthesis of 1, 3, 4-oxadiazoles. Tetrahedron Lett., 2010, 51(37), 4801-4805.
[http://dx.doi.org/10.1016/j.tetlet.2010.06.139]
[70]
Diao, P.; Ge, Y.; Xu, C.; Zhang, N.; Guo, C. Synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles by visible-light-mediated decarboxylation–cyclization of hydrazides and diketones. Tetrahedron Lett., 2018, 59(8), 767-770.
[http://dx.doi.org/10.1016/j.tetlet.2018.01.037]
[71]
Pouliot, M.F.; Angers, L.; Hamel, J.D.; Paquin, J.F. Synthesis of 1,3,4-oxadiazoles from 1,2-diacylhydrazines using [Et2NSF2]BF4 as a practical cyclodehydration agent. Org. Biomol. Chem., 2012, 10(5), 988-993.
[http://dx.doi.org/10.1039/C1OB06512B] [PMID: 22159592]
[72]
Li, Z.; Zhu, A.; Mao, X.; Sun, X.; Gong, X. Silica-supported dichlorophosphate: A recoverable cyclodehydrant for the eco-friendly synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles under solvent-free and microwave irradiation conditions. J. Braz. Chem. Soc., 2008, 19(8), 1622-1626.
[http://dx.doi.org/10.1590/S0103-50532008000800024]
[73]
Gurupadaswamy, H.D.; Girish, V.; Kavitha, C.V.; Raghavan, S.C.; Khanum, S.A. Synthesis and evaluation of 2,5-di(4-aryloylaryloxymethyl)-1,3,4-oxadiazoles as anti-cancer agents. Eur. J. Med. Chem., 2013, 63, 536-543.
[http://dx.doi.org/10.1016/j.ejmech.2013.02.040] [PMID: 23535322]
[74]
Sharma, G.V.; Begum, A. Rake; Krishna, PR. Zirconium (IV) chloride mediated cyclodehydration of 1, 2-diacylhydrazines: a convenient synthesis of 2, 5-diaryl 1, 3, 4-oxadiazoles. Synth. Commun., 2004, 34(13), 2387-2391.
[http://dx.doi.org/10.1081/SCC-120039492]
[75]
Qiao, J.X.; Wang, T.C.; Hu, C.; Li, J.; Wexler, R.R.; Lam, P.Y. Transformation of anionically activated trifluoromethyl groups to heterocycles under mild aqueous conditions. Org. Lett., 2011, 13(7), 1804-1807.
[http://dx.doi.org/10.1021/ol200326u] [PMID: 21381681]
[76]
Ramazani, A.; Rezaei, A. Novel one-pot, four-component condensation reaction: an efficient approach for the synthesis of 2,5-disubstituted 1,3,4-oxadiazole derivatives by a Ugi-4CR/aza-Wittig sequence. Org. Lett., 2010, 12(12), 2852-2855.
[http://dx.doi.org/10.1021/ol100931q] [PMID: 20481612]
[77]
Rajapakse, H.A.; Zhu, H.; Young, M.B.; Mott, B.T. A mild and efficient one pot synthesis of 1, 3, 4-oxadiazoles from carboxylic acids and acyl hydrazides. Tetrahedron Lett., 2006, 47(28), 4827-4830.
[http://dx.doi.org/10.1016/j.tetlet.2006.05.051]
[78]
Kangani, C.O.; Kelley, D.E.; Day, B.W. One pot direct synthesis of oxazolines, benzoxazoles, and oxadiazoles from carboxylic acids using the Deoxo-Fluor reagent. Tetrahedron Lett., 2006, 47(37), 6497-6499.
[http://dx.doi.org/10.1016/j.tetlet.2006.07.032]
[79]
Kudelko, A. Zieliński, W. Microwave-assisted synthesis of 2-styryl-1, 3, 4-oxadiazoles from cinnamic acid hydrazide and triethyl orthoesters. Tetrahedron Lett., 2012, 53(1), 76-77.
[http://dx.doi.org/10.1016/j.tetlet.2011.10.152]
[80]
Polshettiwar, V.; Varma, R.S. Greener and rapid access to bio-active heterocycles: one-pot solvent-free synthesis of 1, 3, 4-oxadiazoles and 1, 3, 4-thiadiazoles. Tetrahedron Lett., 2008, 49(5), 879-883.
[http://dx.doi.org/10.1016/j.tetlet.2007.11.165]
[81]
Kumar, R.; Abdullan, M.M. Synthesis, characterization and anticonvulsant potential of 2,5-disubstituted-1,3,4-oxadiazole analogues. Asian J. Chem., 2019, 31(6), 1389-1397.
[http://dx.doi.org/10.14233/ajchem.2019.22061]
[82]
Kumar, R.; Abdullah, M.M. Synthesis and anticonvulsant potential of some new 4-[5-substituted-[1, 3, 4] oxadiazole-2-yl]-2-phenylquinolines. Indian J. Heterocycl. Chem., 2019, 29(1), 79-86.
[83]
Joule, J.A. Mills, K Heterocyclic chemistry; John Wiley & Sons, 2008.
[84]
Balaban, A.T.; Oniciu, D.C.; Katritzky, A.R. Aromaticity as a cornerstone of heterocyclic chemistry. Chem. Rev., 2004, 104(5), 2777-2812.
[http://dx.doi.org/10.1021/cr0306790] [PMID: 15137807]
[85]
Hemming, K. 1, 2, 4-oxadiazoles. InComprehensive Heterocyclic Chemistry, 2008, III, 243-314. [Elsevier Ltd.
[86]
Sławiński, J.; Szafrański, K.; Pogorzelska, A.; Żołnowska, B.; Kawiak, A.; Macur, K.; Belka, M.; Bączek, T. Novel 2-benzylthio-5-(1,3,4-oxadiazol-2-yl)benzenesulfonamides with anticancer activity: Synthesis, QSAR study, and metabolic stability. Eur. J. Med. Chem., 2017, 132, 236-248.
[http://dx.doi.org/10.1016/j.ejmech.2017.03.039] [PMID: 28364658]
[87]
Roy, P.P.; Bajaj, S.; Maity, T.K.; Singh, J. Synthesis and evaluation of anticancer activity of 1, 3, 4-oxadiazole derivatives against Ehrlich ascites carcinoma bearing mice and their correlation with histopathology of liver. Indian J Pharm Educ., 2017, 15, 16.
[http://dx.doi.org/10.5530/ijper.51.2.31]
[88]
Chaves, J.D.S.; Tunes, L.G. de J Franco, C.H.; Francisco, T.M.; Corrêa, C.C.; Murta, S.M.F.; Monte-Neto, R.L.; Silva, H.; Fontes, A.P.S.; de Almeida, M.V. Novel gold(I) complexes with 5-phenyl-1,3,4-oxadiazole-2-thione and phosphine as potential anticancer and antileishmanial agents. Eur. J. Med. Chem., 2017, 127, 727-739.
[http://dx.doi.org/10.1016/j.ejmech.2016.10.052] [PMID: 27823888]
[89]
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.
[http://dx.doi.org/10.1016/j.bmc.2013.11.004] [PMID: 24286761]
[90]
Valente, S.; Trisciuoglio, D.; De Luca, T.; Nebbioso, A.; Labella, D.; Lenoci, A.; Bigogno, C.; Dondio, G.; Miceli, M.; Brosch, G.; Del Bufalo, 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.
[http://dx.doi.org/10.1021/jm500303u] [PMID: 24972008]
[91]
Rashid, M.; Husain, A.; Mishra, R.; Karim, S.; Khan, S.; Ahmad, M.; Al-wabel, N.; Husain, A.; Ahmad, A.; Khan, S.A. Design and synthesis of benzimidazoles containing substituted oxadiazole, thiadiazole and triazolo-thiadiazines as a source of new anticancer agents. Arab. J. Chem., 2019, 12(8), 3202-3224.
[http://dx.doi.org/10.1016/j.arabjc.2015.08.019]
[92]
Kaur, M.; Kaur, M.; Singh, S. A review on anticancer activity of 1, 3, 4-oxadiazole. Int.J.Pharm.Drug Analy, 2018, 6, 499-508.
[93]
Qi, D.Q.; Yu, C.M.; You, J.Z.; Yang, G.H.; Wang, X.J.; Zhang, Y.P. Synthesis, crystal structures, fluorescence and xanthine oxidase inhibitory activity of pyrazole-based 1, 3, 4-oxadiazole derivatives. J. Mol. Struct., 2015, 1100, 421-428.
[http://dx.doi.org/10.1016/j.molstruc.2015.07.067]
[94]
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.
[http://dx.doi.org/10.1016/j.bmcl.2016.04.058] [PMID: 27156770]
[95]
Distinto, S.; Meleddu, R.; Yanez, M.; Cirilli, R.; Bianco, G.; Sanna, M.L.; Arridu, A.; Cossu, P.; Cottiglia, F.; Faggi, C.; Ortuso, F.; Alcaro, S.; Maccioni, E. Drug design, synthesis, in vitro and in silico evaluation of selective monoaminoxidase B inhibitors based on 3-acetyl-2-dichlorophenyl-5-aryl-2,3-dihydro-1,3,4-oxadiazole chemical scaffold. Eur. J. Med. Chem., 2016, 108, 542-552.
[http://dx.doi.org/10.1016/j.ejmech.2015.12.026] [PMID: 26717204]
[96]
Kumar, S. Synthesis and biological activity of 5-substituted-2-amino-1, 3, 4-oxadiazole derivatives. Turk. J. Chem., 2011, 35(1), 99-108.
[97]
Mathew, G.; Krishnan, R.; Antony, M.; Suseelan, M.S. Synthesis, spectral characterization and biocidal studies of copper (ii) complexes of chromen-2-one-3-carboxy hydrazide and 2-(chromen-3′-onyl)-5-(aryl)-1, 3, 4-oxadiazole derivatives. E-J. Chem., 2011, 8(3), 1346-1354.
[http://dx.doi.org/10.1155/2011/240196]
[98]
Bhardwaj, S.; Parashar, B.; Parashar, N.; Sharma, V.K. Microwave assisted synthesis and pharmacological evaluation of some 1, 3, 4-oxadiazole derivatives. Scholar Research Library. Achieves of App Sci Res., 2011, 3(2), 558-567.
[99]
Patel, N.B.; Patel, J.C. Synthesis and antimicrobial activity of 3-(1,3,4-Oxadiazol-2-yl)quinazolin-4(3H)-ones. Sci. Pharm., 2010, 78(2), 171-193.
[http://dx.doi.org/10.3797/scipharm.0912-16] [PMID: 21179342]
[100]
Banday, M.R.; Mattoo, R.H.; Rauf, A. Synthesis, characterization and anti-bacterial activity of 5-(alkenyl)-2-amino-and 2-(alkenyl)-5-phenyl-1, 3, 4-oxadiazoles. J. Chem. Sci., 2010, 122(2), 177-182.
[http://dx.doi.org/10.1007/s12039-010-0019-6]
[101]
Chawla, R.; Arora, A.; Parameswaran, M.K.; Chan, P.; Sharma, D.; Michael, S.; Ravi, T.K. Synthesis of novel 1,3,4-oxadiazole derivatives as potential antimicrobial agents. Acta Pol. Pharm., 2010, 67(3), 247-253.
[PMID: 20524426]
[102]
Salimon, J.; Salih, N.; Hameed, A.; Ibraheem, H.; Yousif, E. Synthesis and antibacterial activity of some new 1, 3, 4-oxadiazole and 1, 3, 4-thiadiazole derivatives. J. Appl. Sci. Res., 2010, 6(7), 866-870.
[103]
Srinivas, K.; Shyamkumar Immadi, S.M.; Dontheboina, G.; Domakonda, A.; Modumpally, A. Anticancer and antimicrobial activity of 1-[(5-substituted-1, 3, 4 oxadiazol-2-yl) methyl]-4-benzylpiperazines. Int. J. Phytopharm., 2010, 1(2)
[104]
Fuloria, N.K.; Singh, V.; Shaharyar, M.; Ali, M. Synthesis and antimicrobial evaluation of some new oxadiazoles derived from phenylpropionohydrazides. Molecules, 2009, 14(5), 1898-1903.
[http://dx.doi.org/10.3390/molecules14051898] [PMID: 19471209]
[105]
Ateş O.; Kocabalkanli, A.; Cesur, N.; Otük, G. Synthesis and antimicrobial activity of some 5-aryl-2-[N,N-disubstituted thiocarbamoylthio)acylamino]-1,3,4-oxadiazoles. Farmaco, 1998, 53(8-9), 541-544.
[http://dx.doi.org/10.1016/S0014-827X(98)00063-9] [PMID: 10081816]
[106]
Tabatabai, S.A.; Barghi Lashkari, S.; Zarrindast, M.R.; Gholibeikian, M.; Shafiee, A. Design, synthesis and anticonvulsant activity of 2-(2-phenoxy) phenyl-1, 3, 4-oxadiazole derivatives. Iranian journal of pharmaceutical research. Iran. J. Pharm. Res., 2013, 12(Suppl.), 105-111.
[PMID: 24250678]
[107]
Rajak, H.; Deshmukh, R.; Veerasamy, R.; Sharma, A.K.; Mishra, P.; Kharya, M.D. Novel semicarbazones based 2,5-disubstituted-1,3,4-oxadiazoles: one more step towards establishing four binding site pharmacophoric model hypothesis for anticonvulsant activity. Bioorg. Med. Chem. Lett., 2010, 20(14), 4168-4172.
[http://dx.doi.org/10.1016/j.bmcl.2010.05.059] [PMID: 20558061]
[108]
Kaur, H.; Kumar, S.; Vishwakarma, P.; Sharma, M.; Saxena, K.K.; Kumar, A. Synthesis and antipsychotic and anticonvulsant activity of some new substituted oxa/thiadiazolylazetidinonyl/thiazolidinonylcarbazoles. Eur. J. Med. Chem., 2010, 45(7), 2777-2783.
[http://dx.doi.org/10.1016/j.ejmech.2010.02.060] [PMID: 20392546]
[109]
Bhat, M.A.; Al-Omar, M.A.; Siddiqui, N. Synthesis, anticonvulsant and neurotoxicity of some novel 1, 3, 4-oxadiazole derivatives of phthalimide. Pharma Chem., 2010, 2(2), 1-0.
[110]
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.
[http://dx.doi.org/10.1007/s00044-010-9496-x]
[111]
Somani, R.R.; Kadam, G.; Vohra, R.; Vijayaraghavan, S.; Shirodkar, P.Y. Studies of CNS activities of some mannich bases of 1, 3, 4-oxadiazole. Int. J. Pharmacol., 2010, 6(5), 696-704.
[http://dx.doi.org/10.3923/ijp.2010.696.704]
[112]
Kaur, V.; Kaur, P.; Goswami, M. Pharmacological activities of oxadiazole derivatives: A review. Eur. J. Biomedical., 2018, 5(5), 211-221.
[113]
Yar, M.S.; Akhter, M.W. Synthesis and anticonvulsant activity of substituted oxadiazole and thiadiazole derivatives. Acta Pol. Pharm., 2009, 66(4), 393-397.
[PMID: 19702171]
[114]
Rajak, H.; Singour, P.; Kharya, M.D.; Mishra, P. A novel series of 2,5-disubstituted 1,3,4-oxadiazoles: synthesis and SAR study for their anticonvulsant activity. Chem. Biol. Drug Des., 2011, 77(2), 152-158.
[http://dx.doi.org/10.1111/j.1747-0285.2010.01066.x] [PMID: 21266018]
[115]
Bhutani, R.; Pathak, D.P.; Kapoor, G.; Husain, A.; Kant, R.; Iqbal, M.A. Synthesis, molecular modelling studies and ADME prediction of benzothiazole clubbed oxadiazole-Mannich bases, and evaluation of their anti-diabetic activity through in vivo model. Bioorg. Chem., 2018, 77, 6-15.
[http://dx.doi.org/10.1016/j.bioorg.2017.12.037] [PMID: 29316509]
[116]
Srinivas, S.; Aparna, V. Design, synthesis, biological evaluation and molecular docking studies of novel quinazoline derivatives as GSK-3β inhibitors. World J. Pharm. Pharm. Sci., 2013, 2(6), 5842-5851.

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