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Synthesis and Antimicrobial Evaluation of Pyrazole-4-carboxamide Derivatives
Corresponding Author(s) : Shameem Sultana
Asian Journal of Chemistry,
Vol. 34 No. 9 (2022): Vol 34 Issue 9
Abstract
Microbial resistance to the clinically employed antibiotics becomes a threat to the treatment protocols of microbial infectious diseases. Current work aims to synthesize a novel series of pyrazole-4-carboxamide derivatives (6a-j) in a multicomponent reaction between 1H-pyrazole-4-cabaldehyde and various substituted anilines in the presence of 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene (iPr)/TEMPO/phenol under oxidative amidation condition. All the synthesized derivatives (6a-j) were examined for their antifungal and antibacterial activities. All compounds (6a-j) showed significant antimicrobial potential against Gram-positive bacteria (B. subtilis and S. aureus), Gram-negative bacteria (E. coli and P. seruginosa) and fungal strains (A. niger and C. albicans). Compounds 6a, 6f and 6g exhibited better antimicrobial activities.
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References
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E. Peterson and P. Kaur, Front. Microbiol., 9, 2928 (2018); https://doi.org/10.3389/fmicb.2018.02928
J. Jampilek, Molecules, 24, 3839 (2019); https://doi.org/10.3390/molecules24213839
S. Mert, R. Kasimogullari, T. Ica, F. Colak, A. Altun and S. Ok, Eur. J. Med. Chem., 78, 86 (2014); https://doi.org/10.1016/j.ejmech.2014.03.033
T. Nasr, S. Bondock and S. Eid, Eur. J. Med. Chem., 84, 491 (2014); https://doi.org/10.1016/j.ejmech.2014.07.052
D. Manvar, S. Pelliccia, G. La Regina, V. Famiglini, A. Coluccia, A. Ruggieri, S. Anticoli, J.-C. Lee, A. Basu, O. Cevik, L. Nencioni, A.T. Palamara, C. Zamperini, M. Botta, J. Neyts, P. Leyssen, N. KaushikBasu and R. Silvestri, Eur. J. Med. Chem., 90, 497 (2015); https://doi.org/10.1016/j.ejmech.2014.11.042
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A.A. Bekhit, H.M.A. Ashour, Y.S. Abdel-Ghany, A.D.A. Bekhit and A. Baraka, Eur. J. Med. Chem., 43, 456 (2008); https://doi.org/10.1016/j.ejmech.2007.03.030
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I.M. Kompis, K. Islam and R.L. Then, Chem. Rev., 105, 593 (2005); https://doi.org/10.1021/cr0301144
D.Q. Shi and H. Yao, J. Heterocycl. Chem., 46, 1335 (2009); https://doi.org/10.1002/jhet.224
Z. Liu, X. Guo and G. Liu, Bioorg. Med. Chem. Lett., 25, 1297 (2015); https://doi.org/10.1016/j.bmcl.2015.01.046
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P. Singh, R. Raj, P. Singh, J. Gut, P.J. Rosenthal and V. Kumar, Eur. J. Med. Chem., 71, 128 (2014); https://doi.org/10.1016/j.ejmech.2013.10.079
M. Nivsarkar, D. Thavaselvam, S. Prasanna, M. Sharma and M.P. Kaushik, Bioorg. Med. Chem. Lett., 15, 1371 (2005); https://doi.org/10.1016/j.bmcl.2005.01.011
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F. Kavanagh, Analytical Microbiology, Academic Press: New York & London, vol. II (1972).