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Synthesis, Characterization and Molecular Docking Studies of Novel Mannich Bases of Indole Analogs as Potent Antibacterial and Anticancer Agents
Corresponding Author(s) : V. Padmaja
Asian Journal of Chemistry,
Vol. 35 No. 1 (2023): Vol 35 Issue 1
Abstract
A series of a novel indole analogs (5-substituted-1-methyl/ethyl-3-((5-methyl-1-(morpholino/piperazinmethyl)-1H-pyrazol-3-yl)-imino)indolin-2-one (5a-l) were synthesized via Schiff base and Mannich base mechanism. The structures of synthesized compounds were confirmed by IR, 1H NMR and mass spectral data. The antibacterial activity by was measured by agar diffusion method. Some of the analogs (5b, 5c, 5h, 5i and 5j) showed excellent antibacterial recreation against Staphylococcus aureus, Bacillus subtilis and Escherichia coli, Salmonella paratyphi, Pseudomonas and compounds 5f, 5g, 5i showed good activity against MCF-7 cell line through MTT assay method. The molecular docking studies of novel indole analogs revealed that compound 5i suggests perfect dock rating of -5.826 with glide binding strength of -38.76 Kcal/mol. Dock results of all the compounds were ranged from -5.826 (compound 5i) to -2.792 (compound 5d).
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- T.P. Singh and O.M. Singh, Mini Rev. Med. Chem., 18, 9 (2018); https://doi.org/10.2174/1389557517666170807123201
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References
T.P. Singh and O.M. Singh, Mini Rev. Med. Chem., 18, 9 (2018); https://doi.org/10.2174/1389557517666170807123201
Y. Ouyang, J. Li, X. Chen, X. Fu, S. Sun and Q. Wu, Biomolecules, 11, 894 (2021); https://doi.org/10.3390/biom11060894
B. Salehi, C. Quispe, I. Chamkhi, N. El-Omari, A. Balahbib, J. SharifiRad, A. Bouyahya, M. Akram, M. Iqbal, A.O. Docea, C. Caruntu, G. Leyva-Gómez, A. Dey, M. Martorell, D. Calina, V. López and F. Les, Front. Pharmacol., 11, 592654 (2021); https://doi.org/10.3389/fphar.2020.592654
M. Kucerova-Chlupacova, V. Vyskovska-Tyllova, L. Richterova-Finkova, J. Kunes, V. Buchta, M. Vejsova, P. Paterova, L. Semelkova, O. Jandourek and V. Opletalova, Molecules, 21, 1421 (2016); https://doi.org/10.3390/molecules21111421
M. Bhat, G.K. Nagaraja, P. Divyaraj, N. Harikrishna, K.S.R. Pai, S. Biswas and S.K. Peethamber, RSC Adv., 6, 99794 (2016); https://doi.org/10.1039/c6ra22705h
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
D.-H. He, Y.-C. Zhu, Z.-R. Yang and A.-X. Hu, J. Chin. Chem. Soc., 56, 268 (2009); https://doi.org/10.1002/jccs.200900039
W.R. Tully, C.R. Gardner, R.J. Gillespie and R. Westwood, J. Med. Chem., 34, 2060 (1991); https://doi.org/10.1021/jm00111a021
S. Bala, N. Sharma, A. Kajal, S. Kamboj and V. Saini, Int. J. Med. Chem., 2014, 191072 (2014); https://doi.org/10.1155/2014/191072
R. Gudipati, R.N. Reddy Anreddy and S. Manda, J. Enzyme Inhib. Med. Chem., 26, 813 (2011); https://doi.org/10.3109/14756366.2011.556630
P. Saluja, J.M. Khurana, K. Nikhil and P. Roy, RSC Adv., 4, 34594 (2014); https://doi.org/10.1039/C4RA02917H
R. Soman, S. Sujatha and C. Arunkumar, J. Fluor. Chem., 163, 16 (2014); https://doi.org/10.1016/j.jfluchem.2014.04.002
L.M. Aroua, Asian J. Chem., 32, 1266 (2020); https://doi.org/10.14233/ajchem.2020.22472
A. Padmaja, T. Payani, G.D. Reddy and V. Padmavathi, Eur. J. Med. Chem., 44, 4557 (2009); https://doi.org/10.1016/j.ejmech.2009.06.024
M. Prabhaharan, A.R. Prabakaran, S. Gunasekaran and S. Srinivasan, Spectrochim. Acta A Mol. Biomol. Spectrosc., 123, 392 (2014); https://doi.org/10.1016/j.saa.2013.12.056
J.B. Foresman and M. Frisch, Exploring Chemistry with Electronic Structure Methods, Gaussian Inc., Pittsburgh, edn 2 (1996).
W.S. Hamama, M.A. Gouda, M.H. Badr and H.H. Zoorob, Med. Chem. Res., 22, 3556 (2013); https://doi.org/10.1007/s00044-012-0336-z
B.V. Subrahmanya, L.Y.R. Prasad and A.B. Shaik, Indian J. Pharm. Educ. Res., 51(4S), S679 (2017); https://doi.org/10.5530/ijper.51.4s.99
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