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Microwave-Assisted Synthesis, Molecular Docking Studies and Biological Evaluation of Novel Thiazole, Imidazole-Indole Hybrids
Corresponding Author(s) : Mohd Afroz
Asian Journal of Chemistry,
Vol. 35 No. 3 (2023): Vol 35 Issue 3, 2023
Abstract
The present work deals with the synthesis of novel thiazole, imidazole-indole hybrids 3a-l using microwave assisted method as a green chemistry approach. The title compounds were synthesized in a good yield between 68-85%. All the synthesized structures were confirmed by FT-IR, LC-Mass, 1H NMR and 13C NMR analytical data. All the novel indole derivatives were screened for anticancer activity by MTT assay method against the MCF-7 and SKVO3 cell lines. Compound 3i (IC50 value of 26.98 μg, 36.12 μg) and 3j (IC50 value of 24.11 μg, 38.43 μg) exhibited good anticancer activity as compared to doxorubicin. Further, the synthesized compounds were also screened for antibacterial activity using agar diffusion method, where compounds 3c, 3d, 3f and 3j exhibited good antibacterial activity. Furthermore, the binding pattern and affinity of these new indole towards the active region of EGFR were studied using molecular docking studies and the results were in good agreement with the biological results.
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- M. Henary, C. Kananda, L. Rotolo, B. Savino, E.A. Owens and G. Cravotto, RSC Adv., 10, 14170 (2020); https://doi.org/10.1039/D0RA01378A
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- El-S.T. Ali, Eur. J. Chem., 1, 6 (2014).
- R. Soman, S. Sujatha and C. Arunkumar, J. Fluor. Chem., 163, 16 (2014); https://doi.org/10.1016/j.jfluchem.2014.04.002
- G. Chen, Y. Wang, X. Hao, S. Mu and Q. Sun, Chem. Cent. J., 5, 37 (2017); https://doi.org/10.1186/1752-153X-5-37
- K.P. Leena, M.Z. Subin and C.H. Deepthy, Asian J. Pharm. Clin. Res., 10, 50 (2017).
References
M. Henary, C. Kananda, L. Rotolo, B. Savino, E.A. Owens and G. Cravotto, RSC Adv., 10, 14170 (2020); https://doi.org/10.1039/D0RA01378A
Ö. Güngör and P. Gürkan, Arab. J. Chem., 12, 2244 (2019); https://doi.org/10.1016/j.arabjc.2015.02.009.
N.C. Desai, A.H. Makwana and K.M. Rajpara, J. Saudi Chem. Soc., 20, S334 (2016); https://doi.org/10.1016/j.jscs.2012.12.004
R. Kikkawa, I. Hatanaka, H. Yasuda, N. Kobayashi, Y. Shigeta, H. Terashima, T. Morimura and M. Tsuboshima, Diabetologia, 24, 290 (1983); https://doi.org/10.1007/BF00282716
M. Manimohan, S. Pugalmani and M.A. Sithique, J. Inorg. Organomet. Polym. Mater., 30, 3658 (2020); https://doi.org/10.1007/s10904-020-01487-9
I. Ali, M.N. Lone, Z.A. Al-Othman, A. Al-Warthan and M.M. Sanagi, Curr. Drug Targets, 16, 711 (2015); https://doi.org/10.2174/1389450116666150309115922
A. Alahdal, H. Asfour, S. Ahmed, A. Noor, A. Al-Abd, M. Elfaky and S. Elhady, Molecules, 23, 978 (2018); https://doi.org/10.3390/molecules23040978
P. Kavitha and K. Laxma Reddy, Arab. J. Chem., 9, 640 (2016); https://doi.org/10.1016/j.arabjc.2013.06.018
H. Keypour, M. Mahmoudabadi, A. Shooshtari, M. Bayat, E. Soltani, R. Karamian and S.H.M. Farida, Chem. Data Collect., 26, 100354 (2020); https://doi.org/10.1016/j.cdc.2020.100354
B. Tiperciuc, V. Zaharia, I. Colosi, C. Moldovan, O. Crisan, A. Pirnau, L. Vlase, M. Duma and O. Oniga, J. Heterocycl. Chem., 49, 1407 (2012); https://doi.org/10.1002/jhet.1060
El-S.T. Ali, Eur. J. Chem., 1, 6 (2014).
R. Soman, S. Sujatha and C. Arunkumar, J. Fluor. Chem., 163, 16 (2014); https://doi.org/10.1016/j.jfluchem.2014.04.002
G. Chen, Y. Wang, X. Hao, S. Mu and Q. Sun, Chem. Cent. J., 5, 37 (2017); https://doi.org/10.1186/1752-153X-5-37
K.P. Leena, M.Z. Subin and C.H. Deepthy, Asian J. Pharm. Clin. Res., 10, 50 (2017).