Subscribe to our Newsletter and get informed about new publication regulary and special discounts for subscribers!

ILCPA > Volume 66 > Optimized Synthesis of Novel Pyrazole Based...
< Back to Volume

Optimized Synthesis of Novel Pyrazole Based Thiazole Derivatives and their Antimicrobial Evaluation

Full Text PDF


A series of nitro pyrazole based thiazole derivatives compounds were synthesized by using solid base catalyst. The process was further optimized by setting up the solvent and catalyst ratio. The structures of these compounds were elucidated by spectral (IR, 1H NMR, 13C NMR, mass spectra) analysis. Synthesized compounds were screened for their in vitro antibacterial activity against the representative panel of Gram-positive (Staphylococcus aureus, Streptococcus pyogenes) and Gram-negative (Escherichia coli, Pseudomonas aeruginosa) bacteria. These compounds were tested for their inhibitory action against strains of fungi (Candida albicans, Aspergillus niger, Aspergillus clavatus).


International Letters of Chemistry, Physics and Astronomy (Volume 66)
N. C. Desai and M. J. Bhatt, "Optimized Synthesis of Novel Pyrazole Based Thiazole Derivatives and their Antimicrobial Evaluation", International Letters of Chemistry, Physics and Astronomy, Vol. 66, pp. 109-118, 2016
Online since:
May 2016

[1] E. Akbas, I. Berber, Antibacterial and antifungal activities of new pyrazolo[3, 4-d]pyridazin derivatives, Eur. J. Med. Chem. 40 (2005) 401-405.

DOI: 10.1016/j.ejmech.2004.12.001

[2] S. Manfredini, R. Bazzanini, P.G. Baraldi, M. Guarneri, D. Simoni, M.E. Marongiu, A. Pani, P.L. Colla, E. Tramontano, Pyrazole-related nucleosides. Synthesis and antiviral/antitumor activity of some substituted pyrazole and pyrazolo[4, 3-d]-1, 2, 3-triazin-4-one nucleosides, J. Med. Chem. 35 (1992).

DOI: 10.1021/jm00083a017

[3] C.W. Noell, C.C. Cheng, Pyrazoles. 4. Analogs of 3-(3, 3-dimethyl-1-triazeno)pyrazole-4-carboxamide, J. Med. Chem. 14 (1971) 1245-1246.

DOI: 10.1021/jm00294a037

[4] M. Abdel-Aziz, G.A. Abuo-Rahma, A.A. Hassan, Synthesis of novel pyrazole derivatives and evaluation of their antidepressant and anticonvulsant activities, Eur. J. Med. Chem. 44 (2009) 3480-3487.

DOI: 10.1002/chin.200948129

[5] Z. Ozdemir, H.B. Kandilici, B. Gumusel, U. Calis, A. Bilgin, Synthesis and studies on antidepressant and anticonvulsant activities of some 3-(2-furyl)-pyrazoline derivatives, Eur. J. Med. Chem. 42 (2007) 373-379.

DOI: 10.1016/j.ejmech.2006.09.006

[6] S.Y. Hassan, Synthesis, antibacterial and antifungal activity of some new pyrazoline and pyrazole derivatives, Molecules. 3 (2013) 2683-2711.

DOI: 10.3390/molecules18032683

[7] R.B. Pathak, P.T. Chovatia, H.H. Parekh, Synthesis, antitubercular and antimicrobial evaluation of 3-(4-chlorophenyl)-4-substituted pyrazole derivatives, Bioorg Med Chem Lett. 22 (2012) 5129-5133.

DOI: 10.1016/j.bmcl.2012.05.063

[8] A. Palomer, F. Cabre, J. Pascual, J. Campos, M.A. Trujillo, A. Entrena, M.A. Gallo, L. Garcia, D. Mauleon, A. Espinosa, dentification of novel cyclooxygenase-2 selective inhibitors using pharmacophore models, J. Med. Chem. 45 (2002) 1402-1411.

DOI: 10.1021/jm010458r

[9] D.J. Wustrow, T. Capiris, R. Rubin, J.A. Knobelsdorf, H. Akunne, M.D. Davis, R. MacKenzie, T.A. Pugsley, K.T. Zoski, T.G. Heffner, L.D. Wise, Pyrazolo[1, 5-a]pyrimidine CRF-1 receptor antagonists, Bioorg. Med. Chem. Lett. 18 (1998) 2067-(2070).

DOI: 10.1016/s0960-894x(98)00372-2

[10] T.D. Penning, J. J Talley, S.R. Bertenshaw, J.S. Carter, P.W. Collins, S. Docter, M.J. Graneto, L.F. Lee, J.W. Malecha, J.M. Miyashiro, R.S. Rogers, D.J. Rogier, S.S. Yu, G.D. Anderson, E.G. Burton, J.N. Cogburn, S.A. Gregory, C.M. Koboldt, W.E. Perkins, K. Seibert, A.W. Veenhuizen, Y.Y. Zhang, P.C. Isakson, Pyrazolo[1, 5-a]pyrimidine CRF-1 receptor antagonists , J. Med. Chem. 40 (1997).

DOI: 10.1021/jm960803q

[11] S.R. Joshi, P.G. Mandhane, S.D. Diwakar, S.K. Dabhade, C.H. Gill, Synthesis, analgesic and anti-inflammatory activities of some novel pyrazolines derivatives, Bioorg. Med. Chem. Lett. 20 (2010) 3721-3725.

DOI: 10.1016/j.bmcl.2010.04.082

[12] A.R. Bhat, F. Athar, A. Azam, New derivatives of 3, 5-substituted-1, 4, 2-dioxazoles: synthesis and activity against Entamoeba histolytica, Eur. J. Med. Chem. 44 (2009) 926-936.

DOI: 10.1016/j.ejmech.2008.02.001

[13] Z. Ozdemir, H.B. KandilcI, B. Gümüşel, U. Caliş, A.A. Bilgin, Synthesis and studies on antidepressant and anticonvulsant activities of some 3-(2-furyl)-pyrazoline derivatives, Eur J Med Chem. 42 (2007) 373-379.

DOI: 10.1016/j.ejmech.2006.09.006

[14] K. Manna, Y.K. Agrawal, Microwave assisted synthesis of new indophenazine 1, 3, 5-trisubstruted pyrazoline derivatives of benzofuran and their antimicrobial activity, Bioorg. Med. Chem. Lett. 19 (2009) 2688-2692.

DOI: 10.1016/j.bmcl.2009.03.161

[15] Z.A. Kaplancikli, G. Turan-Zitouni, A. Ozdemir, O.D. Can, P. Chevallet, Synthesis and antinociceptive activities of some pyrazoline derivatives, Eur. J. Med. Chem. 44 (2009) 2606-2610.

DOI: 10.1016/j.ejmech.2008.09.002

[16] A. Marella, M. Shaquiquzzaman, M. Akhter, G. Verma, M.M. Alam, Novel pyrazole-pyrazoline hybrids endowed with thioamide as antimalarial agents: their synthesis and 3D-QSAR studies , J Enzyme Inhib Med Chem, 30 (2015) 597-606.

DOI: 10.3109/14756366.2014.958081

[17] I. Braulio, T. Alexis, O. Fabian, Q. Jairo, A. Rodrigo, N. Manuel, S. Adolfo, C. Justo, Synthesis of novel pyrazolic analogues of chalcones and their 3-aryl-4-(3-aryl-4, 5-dihydro-1H-pyrazol-5-yl)-1-phenyl-1H-pyrazole derivatives as potential antitumor agents, Bioorg. Med. Chem. 18 (2010).

DOI: 10.1016/j.bmc.2010.06.013

[18] T.S. Jeong, K.S. Kim, J.R. Kim, K.Y. Cho, S. Lee, W.S. Lee, Novel 3, 5-diaryl pyrazolines and pyrazole as low-density lipoprotein (LDL) oxidation inhibitor, Bioorg. Med. Chem. Lett. 14 (2004) 2719-2723.

DOI: 10.1002/chin.200438126

[19] A. Budakoti, A.R. Bhat, A. Azam, Synthesis of new 2-(5-substituted-3-phenyl-2-pyrazolinyl)-1, 3-thiazolino[5, 4-b]quinoxaline derivatives and evaluation of their antiamoebic activity, Eur. J. Med. Chem. 44 (2009) 1317-1325.

DOI: 10.1016/j.ejmech.2008.02.002

[20] H. Faisal, S. Attar, U. Sadiq, A. Amir, Synthesis, characterization, antiamoebic activity and cytotoxicity of novel 2-(quinolin-8-yloxy) acetohydrazones and their cyclized products (1, 2, 3-thiadiazole and 1, 2, 3-selenadiazole derivatives), Eur. J. Med. Chem. 45 (2010).

DOI: 10.1016/j.ejmech.2010.09.066

[21] Z. Ratkovic, Z.D. Juranic, T. Stanojkovic, D. Manojlovic, R.D. Vukicevic, N. Radulovic, M.D. Joksović, Synthesis, characterization, electrochemical studies and antitumor activity of some new chalcone analogues containing ferrocenyl pyrazole moiety, Bioorg. Chem. 38 (2010).

DOI: 10.1016/j.bioorg.2009.09.003

[22] A.A. Bekhit, T. Abdel-Aziem, Design, synthesis and biological evaluation of some pyrazole derivatives as anti-inflammatory-antimicrobial agents, Bioorg. Med. Chem. 12 (2004) 1935-(1945).

DOI: 10.1016/j.bmc.2004.01.037

[23] A. Kaplancikli, G. Turan-Zitouni, A. Ozdemir, Synthesis and antinociceptive activities of some pyrazoline derivatives, Eur. J. Med. Chem. 44 (2009) 2606-2610.

DOI: 10.1016/j.ejmech.2008.09.002

[24] M.G. Mamolo, D. Zampieri, V. Falagiani, L. Vio, E. Banfi. Synthesis and antimycobacterial activity of 5-aryl-1-isonicotinoyl-3-(pyridin-2-yl)-4, 5-dihydro-1H-pyrazole derivatives, Farmaco 56 (2001) 593-599.

DOI: 10.1016/s0014-827x(01)01098-9

[25] H. Khalilullah, S. Khan, M.J. Ahsan, B. Ahmed, Synthesis and antihepatotoxic activity of 5-(2, 3-dihydro-1, 4-benzodioxane-6-yl)-3-substituted-phenyl-4, 5-dihydro-1H-pyrazole derivatives, Bioorg. Med. Chem. Lett, 21 (2011) 7251-7254.

DOI: 10.1016/j.bmcl.2011.10.056

[26] M.A. Berghot, E.B. Moawad, Convergent synthesis and antibacterial activity of pyrazole and pyrazoline derivatives of diazepam, Eur. J. Pharm. Sci. 20 (2003) 173-179.

DOI: 10.1016/s0928-0987(03)00162-3

[27] L. Gomez, M.D. Hack, J. Wu J.J.M. Wiener, H. Venkatesan, Jr. A. Santillan, D.J. Pippel, N. Mani, B.J. Morrow, S.T. Motley, K.J. Shaw, R. Wolin, C.A. Grice, T.K. Jones, Novel pyrazole derivatives as potent inhibitors of type II topoisomerases. Part 1: synthesis and preliminary SAR analysis, Bioorg. Med. Chem. Lett. 17 (2007).

DOI: 10.1016/j.bmcl.2007.03.003

[28] A. Tanitame,Y. Oyamada, K. Ofuji, M. Fujimoto, N. Iwai, Y. Hiyama, K Suzuki, H. Ito, K. Nagai, M. Wachi, J.I. Yamagishi, Synthesis and antibacterial activity of a novel series of potent DNA gyrase inhibitors. Pyrazole derivatives, J. Med. Chem. 47 (2004).

DOI: 10.1021/jm030394f

[29] B.J. Bradbury, M.J. Pucci , Recent advances in bacterial topoisomerase inhibitors , Curr. Opin. Pharmacol. 8 (2008) 574-581.

[30] N. Siddiqui, S.K. Arya, W. Ahsan, B. Azad, Diverse biological activities of Thiazoles: A Retrospect, Int. j. drug dev. Res, 3 (2001) 55-67.

[31] R. Lesyk, B. S. Zimenkovsky, 4-Thiazolidones: centenarian history, current status and perspectives for modern organic and medicinal chemistry, Curr. Org. Chem. 8 (2004) 1547-1577.

DOI: 10.2174/1385272043369773

[32] N. C. Desai, N. Shihory, M. Bhatt, B. Patel, T. Karkar, Studies on Antimicrobial Evaluation of Some 1-(1-(1H-Benzo[d]imidazol-2-yl)ethylidene)amino)-6-(arylidene)amino)-2-oxo-4-phenyl-1, 2-dihydropyridine-3, 5-dicarbonitriles , Synth Commun, 45 (2015).

DOI: 10.1080/00397911.2015.1102286

[33] N. C. Desai, N. Bhatt, A. Dodiya, T. Karkar, B. Patel, M. Bhatt, Synthesis, characterization and antimicrobial screening of thiazole based 1, 3, 4-oxadiazoles heterocycles, Res. Chem. Intermed. (2016) 3039 -3053.

DOI: 10.1007/s11164-015-2196-x

[34] N. C. Desai V. V. Joshi, K. M. Rajpara, H. V. Vaghani, H.M. Satodiya, Facile synthesis of novel fluorine containing pyrazole based thiazole derivatives and evaluation of antimicrobial activity, J. Fluorine Chem. 142 (2012) 67–78.

DOI: 10.1016/j.jfluchem.2012.06.021
Show More Hide