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Mini-Reviews in Organic Chemistry

Editor-in-Chief

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

Review Article

A Brief Review on Antimicrobial Potential of Pyrazoles (From 2010-2018)

Author(s): Anshul Bansal*

Volume 17, Issue 2, 2020

Page: [197 - 222] Pages: 26

DOI: 10.2174/1570193X16666190122162920

Price: $65

Abstract

In the last few decades, pyrazole chemistry has attracted chemists’ and biologists’ attention mainly due to the discovery of the interesting properties of a great number of pyrazole derivatives. The resulting proliferation of research literature reflects the enormous biological potential of pyrazole derivatives as antitumor, anti-inflammatory, anti-HIV and antimicrobial agents. This review focuses on research concerning the antimicrobial activity of pyrazole derivatives conducted from 2010-2018, and is intended to assist in the development of a new generation of antimicrobial drugs.

Keywords: Anti-inflammatory, antimicrobial, antitumor, ceftriaxone, pyrazole, coumarin derivatives.

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[1]
Perea, S.; Patterson, T.F. Antifungal resistance in pathogenic fungi. Clin. Infect. Dis., 2002, 35(9), 1073-1080.
[http://dx.doi.org/10.1086/344058] [PMID: 12384841]
[2]
Menozzi, G.; Merello, L.; Fossa, P.; Schenone, S.; Ranise, A.; Mosti, L.; Bondavalli, F.; Loddo, R.; Murgioni, C.; Mascia, V.; La Colla, P.; Tamburini, E. Synthesis, antimicrobial activity and molecular modeling studies of halogenated 4-[1H-imidazol-1-yl(phenyl)methyl]-1,5-diphenyl-1H-pyrazoles. Bioorg. Med. Chem., 2004, 12(20), 5465-5483.
[http://dx.doi.org/10.1016/j.bmc.2004.07.029] [PMID: 15388173]
[3]
Hafez, H.N.; El-Gazzar, A.R. Synthesis of pyranopyrazolo N-glycoside and pyrazolopyranopyrimidine C-glycoside derivatives as promising antitumor and antimicrobial agents. Acta Pharm., 2015, 65(3), 215-233.
[http://dx.doi.org/10.1515/acph-2015-0022] [PMID: 26431102]
[4]
Hafez, H.N.; Hussein, H.A.R.; El-Gazzar, A.R. Synthesis of substituted thieno[2,3-d]pyrimidine-2,4-dithiones and their S-glycoside analogues as potential antiviral and antibacterial agents. Eur. J. Med. Chem., 2010, 45(9), 4026-4034.
[http://dx.doi.org/10.1016/j.ejmech.2010.05.060] [PMID: 20691339]
[5]
Karthikeyan, M.S.; Holla, B.S.; Kumari, N.S. Synthesis and antimicrobial studies on novel chloro-fluorine containing hydroxy pyrazolines. Eur. J. Med. Chem., 2007, 42(1), 30-36.
[http://dx.doi.org/10.1016/j.ejmech.2006.07.011] [PMID: 17007964]
[6]
Turan-Zitouni, G.; Ozdemir, A.; Güven, K. Synthesis of some 1-[(N, N-disubstituted thiocar bamoylthio)acetyl]-3-(2-thienyl)-5-aryl-2-pyrazoline derivatives and investigation of their antibacterial and antifungal activities. Arch. Pharm. (Weinheim), 2005, 338(2-3), 96-104.
[http://dx.doi.org/10.1002/ardp.200400935] [PMID: 15765490]
[7]
El-Feky, S.A.; Abd El-Samii, Z.K.; Osman, N.A.; Lashine, J.; Kamel, M.A.; Thabet, H.K. Synthesis, molecular docking and anti-inflammatory screening of novel quinoline incorporated pyrazole derivatives using the Pfitzinger reaction II. Bioorg. Chem., 2015, 58, 104-116.
[http://dx.doi.org/10.1016/j.bioorg.2014.12.003] [PMID: 25590381]
[8]
Alegaon, S.G.; Alagawadi, K.R.; Garg, M.K.; Dushyant, K.; Vinod, D. 1,3,4-Trisubstituted pyrazole analogues as promising anti-inflammatory agents. Bioorg. Chem., 2014, 54, 51-59.
[http://dx.doi.org/10.1016/j.bioorg.2014.04.001] [PMID: 24793214]
[9]
Aggarwal, R.; Bansal, A.; Rozas, I.; Kelly, B.; Kaushik, P.; Kaushik, D. Synthesis, biological evaluation and molecular modeling study of 5-trifluoromethyl-Δ2-pyrazoline and isomeric 5/3-trifluoromethylpyrazole derivatives as anti-inflammatory agents. Eur. J. Med. Chem., 2013, 70, 350-357.
[http://dx.doi.org/10.1016/j.ejmech.2013.09.052] [PMID: 24177361]
[10]
Abdel-Aziz, M. Abuo-Rahma, Gel-D.; Hassan, A.A. Synthesis of novel pyrazole derivatives and evaluation of their antidepressant and anticonvulsant activities. Eur. J. Med. Chem., 2009, 44(9), 3480-3487.
[http://dx.doi.org/10.1016/j.ejmech.2009.01.032] [PMID: 19268406]
[11]
Palaska, E.; Aytemir, M.; Uzbay, I.T.; Erol, D. Synthesis and antidepressant activities of some 3,5-diphenyl-2-pyrazolines. Eur. J. Med. Chem., 2001, 36(6), 539-543.
[http://dx.doi.org/10.1016/S0223-5234(01)01243-0] [PMID: 11525844]
[12]
Abd-El Gawad, N.M.; Hassan, G.S.; Georgey, H.H. Design and synthesis of some pyrazole derivatives of expected anti-inflammatory and analgesic activities. Med. Chem. Res., 2012, 21, 983-994.
[http://dx.doi.org/10.1007/s00044-011-9606-4]
[13]
Reddy, T.S.; Kulhari, H.; Reddy, V.G.; Bansal, V.; Kamal, A.; Shukla, R. Design, synthesis and biological evaluation of 1,3-diphenyl-1H-pyrazole derivatives containing benzimidazole skeleton as potential anticancer and apoptosis inducing agents. Eur. J. Med. Chem., 2015, 101, 790-805.
[http://dx.doi.org/10.1016/j.ejmech.2015.07.031] [PMID: 26231080]
[14]
Wen, J.; Bao, Y.; Niu, Q.; Yang, J.; Fan, Y.; Li, J.; Jing, Y.; Zhao, L.; Liu, D. Identification of N-(6-mercaptohexyl)-3-(4-pyridyl)-1H-pyrazole-5-carboxamide and its disulfide prodrug as potent histone deacetylase inhibitors with in vitro and in vivo anti-tumor efficacy. Eur. J. Med. Chem., 2016, 109, 350-359.
[http://dx.doi.org/10.1016/j.ejmech.2016.01.013] [PMID: 26814680]
[15]
Khunt, R.C.; Khedkar, V.M.; Chawda, R.S.; Chauhan, N.A.; Parikh, A.R.; Coutinho, E.C. Synthesis, antitubercular evaluation and 3D-QSAR study of N-phenyl-3-(4-fluorophenyl)-4-substituted pyrazole derivatives. Bioorg. Med. Chem. Lett., 2012, 22(1), 666-678.
[http://dx.doi.org/10.1016/j.bmcl.2011.10.059] [PMID: 22104148]
[16]
Kantevari, S.; Addla, D.; Bagul, P.K.; Sridhar, B.; Banerjee, S.K. Synthesis and evaluation of novel 2-butyl-4-chloro-1-methyl-imidazole embedded chalcones and pyrazoles as Angiotensin Converting Enzyme (ACE) inhibitors. Bioorg. Med. Chem., 2011, 19(16), 4772-4781.
[http://dx.doi.org/10.1016/j.bmc.2011.06.085] [PMID: 21782455]
[17]
Hasui, T.; Matsunaga, N.; Ora, T.; Ohyabu, N.; Nishigaki, N.; Imura, Y.; Igata, Y.; Matsui, H.; Motoyaji, T.; Tanaka, T.; Habuka, N.; Sogabe, S.; Ono, M.; Siedem, C.S.; Tang, T.P.; Gauthier, C.; De Meese, L.A.; Boyd, S.A.; Fukumoto, S. Identification of benzoxazin-3-one derivatives as novel, potent, and selective nonsteroidal mineralocorticoid receptor antagonists. J. Med. Chem., 2011, 54(24), 8616-8631.
[http://dx.doi.org/10.1021/jm2011645] [PMID: 22074142]
[18]
Griffith, D.A.; Dow, R.L.; Huard, K.; Edmonds, D.J.; Bagley, S.W.; Polivkova, J.; Zeng, D.; Garcia-Irizarry, C.N.; Southers, J.A.; Esler, W.; Amor, P.; Loomis, K.; McPherson, K.; Bahnck, K.B.; Préville, C.; Banks, T.; Moore, D.E.; Mathiowetz, A.M.; Menhaji-Klotz, E.; Smith, A.C.; Doran, S.D.; Beebe, D.A.; Dunn, M.F. Spirolactam-based Acetyl-CoA carboxylase inhibitors: Toward improved metabolic stability of a chromanone lead structure. J. Med. Chem., 2013, 56(17), 7110-7119.
[http://dx.doi.org/10.1021/jm401033t] [PMID: 23981033]
[19]
Huard, K.; Bagley, S.W.; Menhaji-Klotz, E.; Préville, C.; Southers, J.A., Jr; Smith, A.C.; Edmonds, D.J.; Lucas, J.C.; Dunn, M.F.; Allanson, N.M.; Blaney, E.L.; Garcia-Irizarry, C.N.; Kohrt, J.T.; Griffith, D.A.; Dow, R.L. Synthesis of spiropiperidine lactam acetyl-CoA carboxylase inhibitors. J. Org. Chem., 2012, 77(22), 10050-10057.
[http://dx.doi.org/10.1021/jo3014808] [PMID: 23127254]
[20]
Bekhit, A.A.; Hassan, A.M.; Abd El Razik, H.A.; El-Miligy, M.M.; El-Agroudy, E.J. Bekhit, Ael-D. New heterocyclic hybrids of pyrazole and its bioisosteres: design, synthesis and biological evaluation as dual acting antimalarial-antileishmanial agents. Eur. J. Med. Chem., 2015, 94, 30-44.
[http://dx.doi.org/10.1016/j.ejmech.2015.02.038] [PMID: 25768697]
[21]
González Cabrera, D.; Douelle, F.; Feng, T.S.; Nchinda, A.T.; Younis, Y.; White, K.L.; Wu, Q.; Ryan, E.; Burrows, J.N.; Waterson, D.; Witty, M.J.; Wittlin, S.; Charman, S.A.; Chibale, K. Novel orally active antimalarial thiazoles. J. Med. Chem., 2011, 54(21), 7713-7719.
[http://dx.doi.org/10.1021/jm201108k] [PMID: 21966980]
[22]
Sakya, S.M.; Rast, B. Efficient synthesis of 5-alkyl amino and thioether substituted pyrazoles. Tetrahedron Lett., 2003, 44, 7629-7632.
[http://dx.doi.org/10.1016/j.tetlet.2003.08.054]
[23]
Huang, Y.R.; Katzenellenbogen, J.A. Regioselective synthesis of 1,3,5-triaryl-4-alkylpyrazoles: Novel ligands for the estrogen receptor. Org. Lett., 2000, 2(18), 2833-2836.
[http://dx.doi.org/10.1021/ol0062650] [PMID: 10964377]
[24]
Biava, M.; Porretta, G.C.; Cappelli, A.; Vomero, S.; Manetti, F.; Botta, M.; Sautebin, L.; Rossi, A.; Makovec, F.; Anzini, M. 1,5-Diarylpyrrole-3-acetic acids and esters as novel classes of potent and highly selective cyclooxygenase-2 inhibitors. J. Med. Chem., 2005, 48(9), 3428-3432.
[http://dx.doi.org/10.1021/jm049121q] [PMID: 15857149]
[25]
Ahlström, M.M.; Ridderström, M.; Zamora, I.; Luthman, K. CYP2C9 structure-metabolism relationships: Optimizing the metabolic stability of COX-2 inhibitors. J. Med. Chem., 2007, 50(18), 4444-4452.
[http://dx.doi.org/10.1021/jm0705096] [PMID: 17696334]
[26]
Yang, L.; Okuda, F.; Kobayashi, K.; Nozaki, K.; Tanabe, Y.; Ishii, Y.; Haga, M.A. Syntheses and phosphorescent properties of blue emissive iridium complexes with tridentate pyrazolyl ligands. Inorg. Chem., 2008, 47(16), 7154-7165.
[http://dx.doi.org/10.1021/ic800196s] [PMID: 18642898]
[27]
Chang, E.M.; Lee, C.T.; Chen, C.Y.; Wong, F.F.; Yeh, M.Y. synthesis, optical properties, and characterization of new soluble conjugated poly(p-phenylenevinylene) derivatives constituted of alternating pyrazole and 1,3,4-oxadiazole moieties. Aust. J. Chem., 2008, 61(5), 342-349.
[http://dx.doi.org/10.1071/CH07381]
[28]
Chang, S.Y.; Chen, J.L.; Chi, Y.; Cheng, Y.M.; Lee, G.H.; Jiang, C.M.; Chou, P.T. Blue-emitting platinum(II) complexes bearing both pyridylpyrazolate chelate and bridging pyrazolate ligands: Synthesis, structures, and photophysical properties. Inorg. Chem., 2007, 46(26), 11202-11212.
[http://dx.doi.org/10.1021/ic701586c] [PMID: 18027932]
[29]
Cavero, E.; Uriel, S.; Romero, P.; Serrano, J.L.; Giménez, R. Tetrahedral zinc complexes with liquid crystalline and luminescent properties: Interplay between nonconventional molecular shapes and supramolecular mesomorphic order. J. Am. Chem. Soc., 2007, 129(37), 11608-11618.
[http://dx.doi.org/10.1021/ja073639c] [PMID: 17713910]
[30]
Ye, C.; Gard, G.L.; Winter, R.W.; Syvret, R.G.; Twamley, B.; Shreeve, J.M. Synthesis of pentafluorosulfanylpyrazole and pentafluorosulfanyl-1,2,3-triazole and their derivatives as energetic materials by click chemistry. Org. Lett., 2007, 9(19), 3841-3844.
[http://dx.doi.org/10.1021/ol701602a] [PMID: 17715932]
[31]
Dedeian, K.; Shi, J.; Shepherd, N.; Forsythe, E.; Morton, D.C. Photophysical and electrochemical properties of heteroleptic tris-cyclometalated iridium(III) complexes. Inorg. Chem., 2005, 44(13), 4445-4447.
[http://dx.doi.org/10.1021/ic050324u] [PMID: 15962944]
[32]
Umesha, K.B.; Rai, K.M.L. Synthesis and antimicrobial activity of pyrazole derivatives via 1,3-dipolar cycloaddition of nitrile imines with ethyl acetoacetate. Bulg. Chem. Commun., 2010, 42, 11-15.
[33]
Rahimizadeh, M.; Pordel, M.; Bakavoli, M.; Rezaeian, S.; Sadeghian, A. Synthesis and antibacterial activity of some new derivatives of pyrazole. World J. Microbiol. Biotechnol., 2010, 26, 317-321.
[http://dx.doi.org/10.1007/s11274-009-0178-0]
[34]
Ragavan, R.V.; Vijayakumar, V.; Kumari, N.S. Synthesis and antimicrobial activities of novel 1,5-diaryl pyrazoles. Eur. J. Med. Chem., 2010, 45(3), 1173-1180.
[http://dx.doi.org/10.1016/j.ejmech.2009.12.042] [PMID: 20053480]
[35]
Gouda, M.A.; Berghot, M.A.; Shoeib, A.I.; Khalil, A.M. Synthesis and antimicrobial of new anthraquinone derivatives incorporating pyrazole moiety. Eur. J. Med. Chem., 2010, 45(5), 1843-1848.
[http://dx.doi.org/10.1016/j.ejmech.2010.01.021] [PMID: 20144494]
[36]
Gouda, M.A.; Berghot, M.A.; Abd El-Ghani, G.E.; Khalil, A.M. Synthesis and antimicrobial activities of some new thiazole and pyrazole derivatives based on 4,5,6,7-tetrahydrobenzothiophene moiety. Eur. J. Med. Chem., 2010, 45(4), 1338-1345.
[http://dx.doi.org/10.1016/j.ejmech.2009.12.020] [PMID: 20064677]
[37]
Wang, D.J.; Fan, L.; Zheng, C.Y.; Fang, Z.D. Synthesis and anti-microbial activity of some new fluorinated 1H-pyrazoles. J. Fluor. Chem., 2010, 131, 584-586.
[http://dx.doi.org/10.1016/j.jfluchem.2010.01.005]
[38]
Abdu Musad, E.; Mohamed, R.; Saeed, B.A.; Vishwanath, B.S.; Rai, K.M.L. 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]
[39]
Siddiqui, Z.N.; Musthafa, T.N.M.; Ahmad, A.; Khan, A.U. Thermal solvent-free synthesis of novel pyrazolyl chalcones and pyrazolines as potential antimicrobial agents. Bioorg. Med. Chem. Lett., 2011, 21(10), 2860-2865.
[http://dx.doi.org/10.1016/j.bmcl.2011.03.080] [PMID: 21507638]
[40]
Vijesh, A.M.; Isloor, A.M.; Telkar, S.; Peethambar, S.K.; Rai, S.; Isloor, N. Synthesis, characterization and antimicrobial studies of some new pyrazole incorporated imidazole derivatives. Eur. J. Med. Chem., 2011, 46(8), 3531-3536.
[http://dx.doi.org/10.1016/j.ejmech.2011.05.005] [PMID: 21620535]
[41]
Kalhor, M.; Mobinikhaledi, A.; Dadras, A.; Tohidpour, M. Synthesis and antimicrobial activity of some novel substituted 1,2,4-triazoles bearing 1,3,4-oxadiazoles or pyrazoles. J. Het. Chem., 2011, 48, 1366-1370.
[http://dx.doi.org/10.1002/jhet.718]
[42]
Boschi, D.; Guglielmo, S.; Aiello, S.; Morace, G.; Borghi, E.; Fruttero, R. Synthesis and in vitro antimicrobial activities of new (cyano-NNO-azoxy)pyrazole derivatives. Bioorg. Med. Chem. Lett., 2011, 21(11), 3431-3434.
[http://dx.doi.org/10.1016/j.bmcl.2011.03.101] [PMID: 21530247]
[43]
Bondock, S.; Khalifa, W.; Fadda, A.A. Synthesis and antimicrobial activity of some new 4-hetarylpyrazole and furo[2,3-c]pyrazole derivatives. Eur. J. Med. Chem., 2011, 46(6), 2555-2561.
[http://dx.doi.org/10.1016/j.ejmech.2011.03.045] [PMID: 21489661]
[44]
Sharma, P.K.; Chandak, N.; Kumar, P.; Sharma, C.; Aneja, K.R. Synthesis and biological evaluation of some 4-functionalized-pyrazoles as antimicrobial agents. Eur. J. Med. Chem., 2011, 46(4), 1425-1432.
[http://dx.doi.org/10.1016/j.ejmech.2011.01.060] [PMID: 21342734]
[45]
Riyadh, S.M. Enaminones as building blocks for the synthesis of substituted pyrazoles with antitumor and antimicrobial activities. Molecules, 2011, 16(2), 1834-1853.
[http://dx.doi.org/10.3390/molecules16021834] [PMID: 21343888]
[46]
Sharshira, E.M.; Hamada, N.M.M. Synthesis and in vitro antimicrobial activity of some pyrazolyl-1-carboxamide derivatives. Molecules, 2011, 16(9), 7736-7745.
[http://dx.doi.org/10.3390/molecules16097736] [PMID: 21909057]
[47]
Faidallah, H.M.; Khan, K.A.; Asiri, A.M. Synthesis and biological evaluation of new 3-trifluoromethylpyrazolesulfonyl-urea and thiourea derivatives as antidiabetic and antimicrobial agents. J. Fluor. Chem., 2011, 132, 131-137.
[http://dx.doi.org/10.1016/j.jfluchem.2010.12.009]
[48]
Kulkarni, N.V.; Kamath, A.; Budagumpi, S.; Revankar, V.K. Pyrazole bridged binuclear transition metal complexes: Synthesis, characterization, antimicrobial activity and DNA binding/cleavage studies. J. Mol. Struct., 2011, 1006, 580-588.
[http://dx.doi.org/10.1016/j.molstruc.2011.10.008]
[49]
Chandrakantha, B.; Isloor, A.M.; Shetty, P.; Isloor, S.; Malladi, S.; Fun, H.K. Synthesis, characterization and antimicrobial activity of novel ethyl 1-(N-substituted)-5-phenyl-1H- pyrazole-4-carboxylate derivatives. Med. Chem. Res., 2012, 21, 2702-2708.
[http://dx.doi.org/10.1007/s00044-011-9796-9]
[50]
Amir, M.; Javed, S.A.; Hassan, M.Z. Synthesis and antimicrobial activity of pyrazolinones and pyrazoles having benzothiazole moiety. Med. Chem. Res., 2012, 21, 1261-1270.
[http://dx.doi.org/10.1007/s00044-011-9642-0]
[51]
Xu, L-L.; Zheng, C.J.; Sun, L.P.; Miao, J.; Piao, H.R. Synthesis of novel 1,3-diaryl pyrazole derivatives bearing rhodanine-3-fatty acid moieties as potential antibacterial agents. Eur. J. Med. Chem., 2012, 48, 174-178.
[http://dx.doi.org/10.1016/j.ejmech.2011.12.011] [PMID: 22192483]
[52]
Sahu, P.K.; Sahu, P.K.; Gupta, S.K.; Thavaselvam, D.; Agarwal, D.D. Synthesis and evaluation of antimicrobial activity of 4H-pyrimido[2,1-b]benzothiazole, pyrazole and benzylidene derivatives of curcumin. Eur. J. Med. Chem., 2012, 54, 366-378.
[http://dx.doi.org/10.1016/j.ejmech.2012.05.020] [PMID: 22683240]
[53]
Pathak, R.B.; Chovatia, P.T.; Parekh, H.H. Synthesis, antitubercular and antimicrobial evaluation of 3-(4-chlorophenyl)-4-substituted pyrazole derivatives. Bioorg. Med. Chem. Lett., 2012, 22(15), 5129-5133.
[http://dx.doi.org/10.1016/j.bmcl.2012.05.063] [PMID: 22695129]
[54]
Sharshira, E.M.; Hamada, N.M.M. Synthesis and antimicrobial evaluation of some pyrazole derivatives. Molecules, 2012, 17(5), 4962-4971.
[http://dx.doi.org/10.3390/molecules17054962] [PMID: 22547318]
[55]
Mohamed, M.F.; Mohamed, M.S.; Shouman, S.A.; Fathi, M.M.; Abdelhamid, I.A. Synthesis and biological evaluation of a novel series of chalcones incorporated pyrazole moiety as anticancer and antimicrobial agents. Appl. Biochem. Biotechnol., 2012, 168(5), 1153-1162.
[http://dx.doi.org/10.1007/s12010-012-9848-8] [PMID: 22948604]
[56]
Desai, N.C.; Joshi, V.V.; Rajpara, K.M.; Vaghani, H.V.; Satodiya, H.M. Facile synthesis of novel fluorine containing pyrazole based thiazole derivatives and evaluation of antimicrobial activity. J. Fluor. Chem., 2012, 142, 67-78.
[http://dx.doi.org/10.1016/j.jfluchem.2012.06.021]
[57]
Reddy, C.S.; Rao, L.S.; Devi, M.V.; Nagaraj, A. Synthesis and antimicrobial activity of linked heterocyclics containing pyrazole and oxadiazoles. J. Het. Chem., 2012, 49, 1038-1043.
[http://dx.doi.org/10.1002/jhet.913]
[58]
Keche, A.P.; Hatnapure, G.D.; Tale, R.H.; Rodge, A.H.; Kamble, V.M. Synthesis, anti-inflammatory and antimicrobial evaluation of novel 1-acetyl-3,5-diaryl-4,5-dihydro (1H) pyrazole derivatives bearing urea, thiourea and sulfonamide moieties. Bioorg. Med. Chem. Lett., 2012, 22(21), 6611-6615.
[http://dx.doi.org/10.1016/j.bmcl.2012.08.118] [PMID: 23026000]
[59]
Mor, S.; Mohil, R.; Kumar, D.; Ahuja, M. Synthesis and antimicrobial activities of some isoxazolyl thiazolyl pyrazoles. Med. Chem. Res., 2012, 21, 3541-3548.
[http://dx.doi.org/10.1007/s00044-011-9859-y]
[60]
El-Sayed, W.A.; Flefel, E.M.; Morsy, E.M.H. Anticancer and antimicrobial activities of some synthesized pyrazole and triazole derivatives. Pharma Chem., 2012, 4(1), 23-32.
[61]
Zheng, C.J.; Xu, L.L.; Sun, L.P.; Miao, J.; Piao, H.R. Synthesis and antibacterial activity of novel 1,3-diphenyl-1H-pyrazoles functionalized with phenylalanine-derived rhodanines. Eur. J. Med. Chem., 2012, 58, 112-116.
[http://dx.doi.org/10.1016/j.ejmech.2012.10.012] [PMID: 23123727]
[62]
Zheng, C.J.; Song, M.X.; Sun, L.P.; Wu, Y.; Hong, L.; Piao, H.R. Synthesis and biological evaluation of 5-aryloxypyrazole derivatives bearing a rhodanine-3-aromatic acid as potential antimicrobial agents. Bioorg. Med. Chem. Lett., 2012, 22(23), 7024-7028.
[http://dx.doi.org/10.1016/j.bmcl.2012.09.107] [PMID: 23099091]
[63]
Khloya, P.; Kumar, P.; Mittal, A.; Aggarwal, N.K.; Sharma, P.K. Synthesis of some novel 4-arylidene pyrazoles as potential antimicrobial agents. Org. Med. Chem. Lett., 2013, 3(1), 9.
[http://dx.doi.org/10.1186/2191-2858-3-9] [PMID: 23981685]
[64]
Kinali-Demirci, S.; Demirci, S.; Kurt, M. Synthesis, structure characterization and antimicrobial evaluation of 4-(substituted phenylazo)-3,5-diacetamido-1H-pyrazoles. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2013, 106, 12-18.
[http://dx.doi.org/10.1016/j.saa.2012.12.074] [PMID: 23353762]
[65]
Malladi, S.; Isloor, A.M.; Isloor, S.; Akhila, D.S.; Fun, H.K. Synthesis, characterization and antibacterial activity of some new pyrazole based Schiff bases. Arab. J. Chem., 2013, 6, 335-340.
[http://dx.doi.org/10.1016/j.arabjc.2011.10.009]
[66]
Hassan, S.Y. Synthesis, antibacterial and antifungal activity of some new pyrazoline and pyrazole derivatives. Molecules, 2013, 18(3), 2683-2711.
[http://dx.doi.org/10.3390/molecules18032683] [PMID: 23449067]
[67]
Vijesh, A.M.; Isloor, A.M.; Shetty, P.; Sundershan, S.; Fun, H.K. New pyrazole derivatives containing 1,2,4-triazoles and benzoxazoles as potent antimicrobial and analgesic agents. Eur. J. Med. Chem., 2013, 62, 410-415.
[http://dx.doi.org/10.1016/j.ejmech.2012.12.057] [PMID: 23385092]
[68]
Horrocks, P.; Pickard, M.R.; Parekh, H.H.; Patel, S.P.; Pathak, R.B. Synthesis and biological evaluation of 3-(4-chlorophenyl)-4-substituted pyrazole derivatives. Org. Biomol. Chem., 2013, 11(29), 4891-4898.
[http://dx.doi.org/10.1039/c3ob27290g] [PMID: 23779132]
[69]
Gaikwad, N.D.; Patil, S.V.; Bobade, V.D. Synthesis and antimicrobial activity of novel thiazole substituted pyrazole derivatives. J. Het. Chem., 2013, 50, 519-527.
[http://dx.doi.org/10.1002/jhet.1513]
[70]
Nagamallu, R.; Kariyappa, A.K. Synthesis and biological evaluation of novel formyl-pyrazoles bearing coumarin moiety as potent antimicrobial and antioxidant agents. Bioorg. Med. Chem. Lett., 2013, 23(23), 6406-6409.
[http://dx.doi.org/10.1016/j.bmcl.2013.09.053] [PMID: 24120538]
[71]
Malladi, S.; Isloor, A.M.; Peethambar, S.K.; Fun, H.K. Synthesis of new 3-aryl-4-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl)-1-phenyl-1H-pyrazole derivatives as potential antimicrobial agents. Med. Chem. Res., 2013, 22, 2654-2664.
[http://dx.doi.org/10.1007/s00044-012-0267-8]
[72]
Pundeer, R. Sushma, Kiran, V.; Sharma, C.; Aneja, K. R.; Prakash, O. Synthesis and evaluation of antibacterial and antifungal activities of new (Z)-3-bromo-4-(1,3-diaryl-1H-pyrazol-4-yl)but-3-en-2-ones and 4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)-1,3-diaryl-1H-pyrazoles. Med. Chem. Res., 2013, 22, 4715-4726.
[http://dx.doi.org/10.1007/s00044-013-0480-0]
[73]
Jayanna, N.D.; Vagdevi, H.M.; Dharshan, J.C.; Raghavendra, R.; Telkar, S.B. Synthesis, antimicrobial, analgesic activity, and molecular docking studies of novel 1-(5,7-dichloro-1,3-benzoxazol-2-yl)-3-phenyl-1H-pyrazole-4-carbaldehyde derivatives. Med. Chem. Res., 2013, 22, 5814-5822.
[http://dx.doi.org/10.1007/s00044-013-0565-9]
[74]
Kendre, B.V.; Landge, M.G.; Jadhav, W.N.; Bhusare, S.R. Synthesis and bioactivities of some new 1H-pyrazole derivatives containing an aryl sulfonate moiety. Chin. Chem. Lett., 2013, 24, 325-328.
[http://dx.doi.org/10.1016/j.cclet.2013.02.016]
[75]
Song, M.X.; Zheng, C.J.; Deng, X.Q.; Sun, L.P.; Wu, Y.; Hong, L.; Li, Y.J.; Liu, Y.; Wei, Z.Y.; Jin, M.J.; Piao, H.R. Synthesis and antibacterial evaluation of rhodanine-based 5-aryloxy pyrazoles against selected methicillin resistant and quinolone-resistant Staphylococcus aureus (MRSA and QRSA). Eur. J. Med. Chem., 2013, 60, 376-385.
[http://dx.doi.org/10.1016/j.ejmech.2012.12.007] [PMID: 23314051]
[76]
Desai, N.C.; Rajpara, K.M.; Joshi, V.V. Synthesis of pyrazole encompassing 2-pyridone derivatives as antibacterial agents. Bioorg. Med. Chem. Lett., 2013, 23(9), 2714-2717.
[http://dx.doi.org/10.1016/j.bmcl.2013.02.077] [PMID: 23511017]
[77]
Mert, S.; Kasımoğulları, R.; İça, T.; Çolak, F.; Altun, A.; Ok, S. Synthesis, structure-activity relationships, and in vitro antibacterial and antifungal activity evaluations of novel pyrazole carboxylic and dicarboxylic acid derivatives. Eur. J. Med. Chem., 2014, 78, 86-96.
[http://dx.doi.org/10.1016/j.ejmech.2014.03.033] [PMID: 24681068]
[78]
Lavanya, G.; Mallikarjuna Reddy, L.; Padmavathi, V.; Padmaja, A. Synthesis and antimicrobial activity of (1,4-phenyl-ene)bis(arylsul-fonylpyrazoles and isoxazoles). Eur. J. Med. Chem., 2014, 73, 187-194.
[http://dx.doi.org/10.1016/j.ejmech.2013.11.041] [PMID: 24398288]
[79]
Aggarwal, R.; Bansal, A.; Rozas, I.; Diez-Cecilia, E.; Kaur, A.; Mahajan, R.; Sharma, J. p-Toluenesulfonic acid-catalyzed solvent-free synthesis and biological evaluation of new 1-(4′,6′-dimethylpyrimidin-2′-yl)-5-amino-4H-3-arylpyrazole derivatives. Med. Chem. Res., 2014, 23, 1454-1464.
[http://dx.doi.org/10.1007/s00044-013-0751-9]
[80]
Kalaria, P.N.; Satasia, S.P.; Raval, D.K. Synthesis, identification and in vitro biological evaluation of some novel 5-imidazopyrazole incorporated pyrazoline and isoxazoline derivatives. New J. Chem., 2014, 38, 2902-2910.
[http://dx.doi.org/10.1039/c4nj00244j]
[81]
Mohil, R.; Kumar, D.; Mor, S. Synthesis and antimicrobial activity of some 1,3-disubstituted indeno[1,2-c]pyrazoles. J. Het. Chem., 2014, 51, 203-209.
[http://dx.doi.org/10.1002/jhet.1081]
[82]
Liu, J.J.; Sun, J.; Fang, Y.B.; Yang, Y.A.; Jiao, R.H.; Zhu, H.L. Synthesis, and antibacterial activity of novel 4,5-dihydro-1H-pyrazole derivatives as DNA gyrase inhibitors. Org. Biomol. Chem., 2014, 12(6), 998-1008.
[http://dx.doi.org/10.1039/c3ob41953c] [PMID: 24382549]
[83]
Chundawat, T.S.; Sharma, N.; Bhagat, S. Synthesis and in vitro antimicrobial evaluation of novel fluorine containing 3-benzofuran-2-yl-5-phenyl-4,5-dihydro-1H-pyrazoles and 3-benzofuran-2-yl-5-phenyl-4,5-dihydro-isoxazoles. Med. Chem. Res., 2014, 23, 1350-1359.
[http://dx.doi.org/10.1007/s00044-013-0735-9]
[84]
Viveka, S. Dinesha, Madhu, L. N.; Nagaraja, G. K. Synthesis of new pyrazole derivatives via multicomponent reaction and evaluation of their antimicrobial and antioxidant activities. Monatsh. Chem., 2015, 146, 1547-1555.
[http://dx.doi.org/10.1007/s00706-015-1428-5]
[85]
Hamada, N.M.M.; Abdo, N.Y.M. Synthesis, characterization, antimicrobial screening and free-radical scavenging activity of some novel substituted pyrazoles. Molecules, 2015, 20(6), 10468-10486.
[http://dx.doi.org/10.3390/molecules200610468] [PMID: 26060913]
[86]
Metwally, N.H.; Abdelrazek, F.M.; Jaafar, M.T. Synthesis and antimicrobial activity of some novel substituted bis-pyridone, pyrazole, and thiazole derivatives. J. Het. Chem., 2015, 52, 358-365.
[http://dx.doi.org/10.1002/jhet.2043]
[87]
Li, Y.R.; Li, C.; Liu, J.C.; Guo, M.; Zhang, T.Y.; Sun, L.P.; Zheng, C.J.; Piao, H.R. Synthesis and biological evaluation of 1,3-diaryl pyrazole derivatives as potential antibacterial and anti-inflammatory agents. Bioorg. Med. Chem. Lett., 2015, 25(22), 5052-5057.
[http://dx.doi.org/10.1016/j.bmcl.2015.10.028] [PMID: 26490095]
[88]
Karabacak, C.; Tilki, T.; Tuncer, B.O.; Cengiz, M. Antimicrobial pyrazole dyes: Synthesis, characterization, and absorption characteristics. Res. Chem. Intermed., 2015, 41, 1985-1999.
[http://dx.doi.org/10.1007/s11164-013-1326-6]
[89]
Basha, S.S.; Divya, K.; Padmaja, A.; Padmavathi, V. Synthesis and antimicrobial activity of thiazolylpyrazoles and isoxazoles. Res. Chem. Intermed., 2015, 41, 10067-10083.
[http://dx.doi.org/10.1007/s11164-015-2013-6]
[90]
Rizk, H.F.; Ibrahim, S.A.; El-Borai, M.A. Synthesis, fastness properties, color assessment and antimicrobial activity of some azo reactive dyes having pyrazole moiety. Dyes Pigments, 2015, 112, 86-92.
[http://dx.doi.org/10.1016/j.dyepig.2014.06.026]
[91]
Doddaramappa, S.D.; Lokanatha Rai, K.M.; Srikantamurthy, N. Chandra; Chethan, J. Novel 5-functionalized-pyrazoles: Synthesis, characterization and pharmacological screening. Bioorg. Med. Chem. Lett., 2015, 25(17), 3671-3675.
[http://dx.doi.org/10.1016/j.bmcl.2015.06.050] [PMID: 26152425]
[92]
Nayak, P.S.; Narayana, B.; Sarojini, B.K.; Fernades, J.; Bharath, B.R.; Madhu, L.N. Synthesis, molecular docking and biological evaluation of novel bis-pyrazole derivatives for analgesic, anti-inflammatory and antimicrobial activities. Med. Chem. Res., 2015, 24, 4191-4206.
[http://dx.doi.org/10.1007/s00044-015-1467-9]
[93]
Surendra Kumar, R.; Arif, I.A.; Ahamed, A.; Idhayadhulla, A. Anti-inflammatory and antimicrobial activities of novel pyrazole analogues. Saudi J. Biol. Sci., 2016, 23(5), 614-620.
[http://dx.doi.org/10.1016/j.sjbs.2015.07.005] [PMID: 27579011]
[94]
Desai, N.C.; Kotadiya, G.M.; Trivedi, A.R.; Khedkar, V.M.; Jha, P.C. Design, synthesis, and biological evaluation of novel fluorinated pyrazole encompassing pyridyl 1,3,4-oxadiazole motifs. Med. Chem. Res., 2016, 25, 2698-2717.
[http://dx.doi.org/10.1007/s00044-016-1683-y]
[95]
Harikrishna, N.; Isloor, A.M.; Ananda, K.; Obaide, A.; Fune, H.K. Synthesis, and antitubercular and antimicrobial activity of 1′-(4-chlorophenyl)pyrazole containing 3,5-disubstituted pyrazoline derivatives. New J. Chem., 2016, 40, 73-76.
[http://dx.doi.org/10.1039/C5NJ02237A]
[96]
Nayak, N.; Ramprasad, J.; Dalimba, U. Synthesis and antitubercular and antibacterial activity of some active fluorine containing quinoline-pyrazole hybrid derivatives. J. Fluor. Chem., 2016, 183, 59-68.
[http://dx.doi.org/10.1016/j.jfluchem.2016.01.011]
[97]
Ramírez-Prada, J.; Robledo, S.M.; Vélez, I.D.; Crespo, M.D.P.; Quiroga, J.; Abonia, R.; Montoya, A.; Svetaz, L.; Zacchino, S.; Insuasty, B. Synthesis of novel quinoline-based 4,5-dihydro-1H-pyrazoles as potential anticancer, antifungal, antibacterial and antiprotozoal agents. Eur. J. Med. Chem., 2017, 131, 237-254.
[http://dx.doi.org/10.1016/j.ejmech.2017.03.016] [PMID: 28329730]
[98]
Chougala, B.M.; Samundeeswari, S.; Holiyachi, M.; Shastri, L.A.; Dodamani, S.; Jalalpure, S.; Dixit, S.R.; Joshi, S.D.; Sunagar, V.A. Synthesis, characterization and molecular docking studies of substituted 4-coumarinylpyrano[2,3-c]pyrazole derivatives as potent antibacterial and anti-inflammatory agents. Eur. J. Med. Chem., 2017, 125, 101-116.
[http://dx.doi.org/10.1016/j.ejmech.2016.09.021] [PMID: 27657808]
[99]
Sharma, A.; Ghabbour, H.; Khan, S.T.; Torre, B.G.; Albericio, F.; El-Faham, A. Novel pyrazolyl-s-triazine derivatives, molecular structure and antimicrobial activity. J. Mol. Struct., 2017, 1145, 244-253.
[http://dx.doi.org/10.1016/j.molstruc.2017.05.040]
[100]
Prabhudeva, M.G.; Prabhuswamy, M. DileepKumar, A.; Lokanath, N.K.; Naveen, S.; Ajay Kumar, K. Synthesis, crystal and molecular structure and antimicrobial studies of 1-(3-chlorophenyl)-3-(5-chlorothiophen-2-yl)-5-phenyl-4,5-dihydro-1H-pyrazole. Chem. Data. Collect., 2017, 9-10, 80-88.
[101]
Rangaswamy, J.; Vijay Kumar, H.; Harini, S.T.; Naik, N. Functionalized 3-(benzofuran-2-yl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole scaffolds: A new class of antimicrobials and antioxidants. Arab. J. Chem., 2017, 10, s2685-s2696.
[http://dx.doi.org/10.1016/j.arabjc.2013.10.012]
[102]
Abrigach, F.; Rokni, Y.; Takfaoui, A.; Khoutoul, M.; Doucet, H.; Asehraou, A.; Touzani, R. In vitro screening, homology modeling and molecular docking studies of some pyrazole and imidazole derivatives. Biomed. Pharmacother., 2018, 103, 653-661.
[http://dx.doi.org/10.1016/j.biopha.2018.04.061] [PMID: 29679907]
[103]
Sowmya, D.V.; Lakshmi Teja, G.; Padmaja, A.; Kamala Prasad, V.; Padmavathi, V. Green approach for the synthesis of thiophenyl pyrazoles and isoxazoles by adopting 1,3-dipolar cycloaddition methodology and their antimicrobial activity. Eur. J. Med. Chem., 2018, 143, 891-898.
[http://dx.doi.org/10.1016/j.ejmech.2017.11.093] [PMID: 29227929]
[104]
Zalaru, C.; Dumitrascu, F.; Draghici, C.; Tarcomnicu, I.; Tatia, R.; Moldovan, L.; Chifiriuc, C.; Lazar, V.; Marinescu, M.; Nitulescu, M.G.; Ferbinteanu, M. Synthesis, spectroscopic characterization, DFT study and antimicrobial activity of novel alkylaminopyrazole derivatives. J. Mol. Struct., 2018, 1156, 12-21.
[http://dx.doi.org/10.1016/j.molstruc.2017.11.073]
[105]
Kovvuri, J.; Nagaraju, B.; Kumar, C.G.; Sirisha, K.; Chandrasekhar, C.; Alarifi, A.; Kamal, A. Catalyst-free synthesis of pyrazole-aniline linked coumarin derivatives and their antimicrobial evaluation. J. Saudi Chem. Soc., 2018, 22, 665-677.
[http://dx.doi.org/10.1016/j.jscs.2017.12.002]
[106]
Prasad, P.; Kalola, A.G.; Patel, M.P. Microwave assisted one-pot synthetic route to imidazo[1,2-a]pyrimidine derivatives of imidazo/triazole clubbed pyrazole and their pharmacological screening. New J. Chem., 2018, 42, 12666-12676.
[http://dx.doi.org/10.1039/C8NJ00670A]
[107]
Zakeyah, A.A.; Whitt, J.; Duke, C.; Gilmore, D.F.; Meeker, D.G.; Smeltzer, M.S.; Alam, M.A. Synthesis and antimicrobial studies of hydrazone derivatives of 4-[3-(2,4-difluorophenyl)-4-formyl-1H-pyrazol-1-yl]benzoic acid and 4-[3-(3,4-difluorophenyl)-4-formyl-1H-pyrazol-1-yl]benzoic acid. Bioorg. Med. Chem. Lett., 2018, 28(17), 2914-2919.
[http://dx.doi.org/10.1016/j.bmcl.2018.07.016] [PMID: 30017319]
[108]
Liu, H.; Ren, Z.L.; Wang, W.; Gong, J.X.; Chu, M.J.; Ma, Q.W.; Wang, J.C.; Lv, X.H. Novel coumarin-pyrazole carboxamide derivatives as potential topoisomerase II inhibitors: Design, synthesis and antibacterial activity. Eur. J. Med. Chem., 2018, 157, 81-87.
[http://dx.doi.org/10.1016/j.ejmech.2018.07.059] [PMID: 30075404]
[109]
Sayed, G.H.; Azab, M.E.; Anwer, K.E.; Raouf, M.A.; Negm, N.A. Pyrazole, pyrazolone and enaminonitrile pyrazole derivatives: Synthesis, characterization and potential in corrosion inhibition and antimicrobial applications. J. Mol. Liq., 2018, 252, 329-338.
[http://dx.doi.org/10.1016/j.molliq.2017.12.156]

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