Copyright (c) 2024 Ranajit Sutradhar
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Characterization, Molecular Docking Studies and Biological Evaluation of Thiazole Schiff Base Analogs
Corresponding Author(s) : Ranajit Kumar Sutradhar
Asian Journal of Chemistry,
Vol. 36 No. 3 (2024): Vol 36 Issue 3, 2024
Abstract
In this work, potentially safe few Schiff base compounds containing a thiazole moiety were synthesized and characterized. Three thiazole derivatives (2a-c) were successfully synthesized through a two-step reaction involving substituted benzaldehyde, thiosemicarbazide and 1,3-dichloroacetone. The elucidation of the synthesized compounds was accomplished by using spectral studies. Antimicrobial activities demonstrated that some compounds exhibited moderate effectiveness against microbes, compared to the standard antibiotic’s ceftriaxone and amphotericin B, using the disc diffusion technique. In the DPPH free radical scavenging assay, all compounds displayed promising antioxidant effectiveness. Moreover, the molecular docking studies showed that thiazole Schiff base analogs effectively bind to potential receptor binding sites.
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References
R.N. Sharma, F.P. Xavier, K.K. Vasu, S.C. Chaturvedi and S.S. Pancholi, J. Enzyme Inhib. Med. Chem., 24, 890 (2009); https://doi.org/10.1080/14756360802519558
W. Hussein and G. Turan-Zitouni, MOJ Bioorganic Org. Chem., 2, 52 (2018); https://doi.org/10.15406/mojboc.2018.02.0056
S. Eryilmaz, E.T. Çelikoglu, Ö. Idil, E. Inkaya, Z. Kozak, E. Misir and M. Gül, Bioorg. Chem., 95, 103476 (2020); https://doi.org/10.1016/j.bioorg.2019.103476
T. Al-Qirim, G. Shattat, K. Sweidan, W. El-Huneidi, G.A. Sheikha, R.A. Khalaf and S. Hikmat, Arch. Pharm., 345, 401 (2012); https://doi.org/10.1002/ardp.201100225
M.V.N. de Souza and M.V. de Almeida, Quim. Nova.,26, 366-372, (2003); https://doi.org/10.1590/s0100-40422003000300014
L.M. Fox and L.D. Saravolatz, Clin. Infect. Dis., 40, 1173 (2005); https://doi.org/10.1086/428839
G.M. Reddy, J.R. Garcia, V.H. Reddy, A.M. de Andrade, A. Camilo Jr., R.A. Pontes Ribeiro and S.R. de Lazaro, Eur. J. Med. Chem., 123, 508 (2016); https://doi.org/10.1016/j.ejmech.2016.07.062
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V. Jaishree, N. Ramdas, J. Sachin and B. Ramesh, J. Saudi Chem. Soc., 16, 371 (2012); https://doi.org/10.1016/j.jscs.2011.02.007
J.F.W. Chan, S. Yuan, K.H. Kok, K.K.W. To, H. Chu, J. Yang, F. Xing, J. Liu, C.C.Y. Yip, R.W.S. Poon, H.W. Tsoi, S.K.F. Lo, K.H. Chan, V.K.M. Poon, W.M. Chan, J.D. Ip, J.P. Cai, V.C.C. Cheng, H. Chen, C.K.M. Hui and K.Y. Yuen, Lancet, 395, 514 (2020); https://doi.org/10.1016/S0140-6736(20)30154-9
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S.M. Sondhi, N. Singh, A. Kumar, O. Lozach and L. Meijer, Bioorg. Med. Chem., 14, 3758 (2006); https://doi.org/10.1016/j.bmc.2006.01.054
A. Kajal, S. Bala, S. Kamboj, N. Sharma and V. Saini, J. Catal., 2013, 893512 (2013); https://doi.org/10.1155/2013/893512
F. Sonmez, Z. Gunesli, B.Z. Kurt, I. Gazioglu, D. Avci and M. Kucukislamoglu, Mol. Divers., 23, 829 (2019); https://doi.org/10.1007/s11030-018-09910-7
M.P. Murphy, A. Holmgren, N.G. Larsson, B. Halliwell, C.J. Chang, B. Kalyanaraman, S.G. Rhee, P.J. Thornalley, L. Partridge, D. Gems, T. Nyström, V. Belousov, P.T. Schumacker and C.C. Winterbourn, Cell Metab. 13, 361 (2011); https://doi.org/10.1016/j.cmet.2011.03.010
R.P. Mason, Redox Biol., 8, 422 (2016); https://doi.org/10.1016/j.redox.2016.04.003
Z. Jin, X. Du, Y. Xu, Y. Deng, M. Liu, Y. Zhao, B. Zhang, X. Li, L. Zhang, C. Peng, Y. Duan, J. Yu, L. Wang, K. Yang, F. Liu, R. Jiang, X. Yang, T. You, X. Liu, X. Yang, F. Bai, H. Liu, X. Liu, L.W. Guddat, W. Xu, G. Xiao, C. Qin, Z. Shi, H. Jiang, Z. Rao and H. Yang, Nature, 582, 289 (2020); https://doi.org/10.1038/s41586-020-2223-y
E.N. Bentz, A.B. Pomilio and R.M. Lobayan, Comput. Theor. Chem., 1110, 14 (2017); https://doi.org/10.1016/j.comptc.2017.03.028
M.S. Shah, M.M. Rahman, M.D. Islam, A. Al-Macktuf, J.U. Ahmed, H. Nishino and M.A. Haque, J. Mol. Struct., 1248, 131465 (2022); https://doi.org/10.1016/j.molstruc.2021.131465
V. Jaishree, N. Ramdas, J. Sachin and B. Ramesh, J. Saudi Chem. Soc., 16, 371 (2012); https://doi.org/10.1016/j.jscs.2011.02.007