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Synthesis and Antimicrobial Assay of Some Novel 4-Thiazolidinone Derivatives Possessing Benzofuran, Quinoline and Pyrazole Moieties
Corresponding Author(s) : M. Idrees
Asian Journal of Chemistry,
Vol. 30 No. 10 (2018): Vol 30 Issue 10, 2018
Abstract
In this study, simple, easy and convenient syntheses of six novel 4-thiazolidinone derivatives (3a-f) bearing benzofuran, quinoline and pyrazole moieties have been described. In the first step, six different carbohydrazides (2a-f) were synthesized by reacting 5-(benzofuran-2-yl)-1-phenyl-1H-pyrazole-3-carbohydrazide (2) with six different 2-(p-tolyloxy)quinoline-3-carbaldehyde (1a-f). Similarly, in second step, 5-(benzofuran-2-yl)-N¢-(2-(2-(p-tolyloxy) substituted quinolin-3-yl)-4-oxothiazolidin-3-yl)-1-phenyl-1H-pyrazole-3-carboxamide (3a-f) was prepared in excellent yield through the interaction of compounds 2a-f with thioglycolic acid in presence of anhydrous zinc chloride. Structural identifications of products 2a and 3a are reported on the basis of IR, 1H NMR, 13C NMR and mass spectra and the analytical data confirms the structure of title compounds. Further, these new products have been assayed for their antimicrobial screening against S. aureus and E. coli as the two selected bacterial strains and two fungi such as C. albicans and A. niger using paper disc diffusion method. Antimicrobial screening revealed that the compounds are good antibacterial agents but found to be inactive against fungi.
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- R. Singh and A. Srivastava, Med. Chem., 44, 1868 (2005).
- K. Kaur, M. Jain, R. Reddy and R. Jain, Eur. J. Med. Chem., 45, 3245 (2010); https://doi.org/10.1016/j.ejmech.2010.04.011.
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- A. Gupta, R. Singh, P. Sonar and S. Saraf, Biochem. Res. Int., Article ID 8086762 (2016); https://doi.org/10.1155/2016/8086762.
- A.P. Liesen, T.M. de Aquino, C.S. Carvalho, V.T. Lima, J.M. de Araújo, J.G. de Lima, A.R. de Faria, E.J.T. de Melo, A.J. Alves and E.W. Alves, Eur. J. Med. Chem., 45, 3685 (2010); https://doi.org/10.1016/j.ejmech.2010.05.017.
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References
R. Singh and A. Srivastava, Med. Chem., 44, 1868 (2005).
K. Kaur, M. Jain, R. Reddy and R. Jain, Eur. J. Med. Chem., 45, 3245 (2010); https://doi.org/10.1016/j.ejmech.2010.04.011.
S. Jain, V. Chandra, P.K. Jain, K. Pathak, D. Pathak and A. Vaidya, Arab. J. Chem.; https://doi.org/10.1016/j.arabjc.2016.10.009.
D.B. Yaakov, Y. Shadkchan, N.A. Dimitrios, P. Kontoyiannis and N. Osherov, J. Antimicrob. Chemother., 72, 2263 (2017); https://doi.org/10.1093/jac/dkx117.
X.-Z. Zou, J.-A. Zhang, L.-J. Zhang, Y.-J. Liu, N. Li, Y. Li, S.-C. Wei and M. Pan, Inorg. Chem. Commun., 54, 21 (2015); https://doi.org/10.1016/j.inoche.2015.01.029.
T. Elavarasan, D. Bhakiarajand and M. Gopalakrishnan, Der Pharma Chem., 6, 391 (2014).
A.K. Jain, A. Vaidya, V. Ravichandran, S.K. Kashaw and R.K. Agrawal, Bioorg. Med. Chem., 20, 3378 (2012); https://doi.org/10.1016/j.bmc.2012.03.069.
P. Samadhiya, R. Sharma, S. Srivastava and S.D. Srivastava, Arab. J. Chem., 7, 657 (2014); https://doi.org/10.1016/j.arabjc.2010.11.015.
D. Kaminskyy, B. Bednarczyk-Cwynar, O. Vasylenko, O. Kazakova, R. Lesyk, B. Zimenkovsky and L. Zaprutko, Med. Chem. Res., 21, 3568 (2012); https://doi.org/10.1007/s00044-011-9893-9.
S. Avdieiev, L. Gera, D. Havrylyuk, R.S. Hodges, R. Lesyk, V. Ribrag, Y. Vassetzky and V. Kavsana, Bioorg. Med. Chem., 22, 3815 (2014); https://doi.org/10.1016/j.bmc.2014.06.046.
P.-C. Lv, C.-F. Zhou, J. Chen, P.-G. Liu, K.-R. Wang, W.-J. Mao, H.-Q. Li, Y. Yang, J. Xiong and H.-L. Zhu, Bioorg. Med. Chem., 18, 314 (2010); https://doi.org/10.1016/j.bmc.2009.10.051.
V. Kumar, A. Sharma and P.C. Sharma, J. Enzym. Inhib. Med. Chem., 26, 198 (2011); https://doi.org/10.3109/14756366.2010.489897.
A. Aly, A. Brown and M. Abdel-Aziz, G. El-Din A.A. Abuo-Rahma, M.F. Radwan, M. Ramadan and A.M. Gamal-Eldeen, J. Heterocycl. Chem., 47, 547 (2010); https://doi.org/10.1002/jhet.290.
S. Riyaz, A. Naidu, P. Dubey, Indian J. Chem., 51B, 1396 (2012).
R. Patel and S. Park, Chem. Biol. Drug Des., 84, 123 (2014); https://doi.org/10.1111/cbdd.12299.
N.B. Patel, V.N. Patel, H.K.R. Patel and J. Patel, Acta Pol. Pharm., 67, 267 (2010).
V. Kumar, A. Kumar, S. Sharma and N.P. Singh, Indian J. Chem., 50B, 1496 (2011).
K. Mistry and K. Desai, E-J. Chem., 1, 189 (2004); https://doi.org/10.1155/2004/590439.
A. Saundane and P. Walmik, J. Chem., Article ID 543815 (2013); https://doi.org/10.1155/2013/543815.
R. George, Eur. J. Med. Chem., 47, 377 (2012); https://doi.org/10.1016/j.ejmech.2011.11.006.
V. Ravichandran, A. Jain, K. Kumar, H. Rajak and R. Agrawal, Chem. Biol. Drug Des., 78, 464 (2011); https://doi.org/10.1111/j.1747-0285.2011.01149.x.
S. Kumar, H. Kaur and A. Kumar, Arab. J. Chem., 5, 475 (2012); https://doi.org/10.1016/j.arabjc.2010.09.014.
A. Gupta, R. Singh, P. Sonar and S. Saraf, Biochem. Res. Int., Article ID 8086762 (2016); https://doi.org/10.1155/2016/8086762.
A.P. Liesen, T.M. de Aquino, C.S. Carvalho, V.T. Lima, J.M. de Araújo, J.G. de Lima, A.R. de Faria, E.J.T. de Melo, A.J. Alves and E.W. Alves, Eur. J. Med. Chem., 45, 3685 (2010); https://doi.org/10.1016/j.ejmech.2010.05.017.
M. Idrees, R.D. Nasare, N.J. Siddiqui, Chem. Sci. Transac., 5, 1090 (2016); https://doi.org/10.7598/cst2016.1323.