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Synthesis, in silico Biological Profile and MMP-9 Inhibitory Activity of Some Isonicotinic Acid Hydrazide Incorporated Novel Indazoles
Corresponding Author(s) : Rajasekhar Komarla Kumarachari
Asian Journal of Chemistry,
Vol. 35 No. 5 (2023): Vol 35 Issue 5, 2023
Abstract
The present study reports the synthesis of isonicotinic acid hydrazide incorporated 7-(substituted benzylidine)-3-aryl-1-(pyridin-4-yl)-methanone)-2,3,4,5,6,7-hexahydro-1H-indazoles from substituted chalcones. The chalcones were synthesized by reacting cyclohexanone with a substituted aromatic aldehydes via the Claisen-Schmidt method. The IR, 1H NMR and mass spectral studies were used to characterize the synthesized compounds. In silico analysis was used to anticipate the biological activities of the synthezised compounds. PASS computer program predicted all title compounds to be anti-inflammatory in nature. All the synthesized compounds were screened for MMP-9 inhibitory activity by the gelatin zymography method. Among all the synthesized compounds B1, B3, B4 and B9 exhibited significant activity whereas rest of the synthesized compounds B2, B5, B6, B7 and B8 exhibited mild to moderate anti-inflammatory activity.
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References
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https://www.who.int/news-room/fact-sheets/detail/cancer
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C. Miao, J. Ma, Y. Zhang, Y. Chu, J. Li, R. Kuai, S. Wang and H. Peng, Int. J. Clin. Exp. Pathol., 8, 10512 (2015).
V. Sivaramakrishnan and S. Niranjali Devaraj, Chem. Biol. Interact., 180, 353 (2009); https://doi.org/10.1016/j.cbi.2009.02.004
R. Hassanzadeh-Makoui, B. Razi, S. Aslani, D. Imani and S.S. Tabaee, BMC Cardiovasc. Disord., 20, 232 (2020); https://doi.org/10.1186/s12872-020-01510-4
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S. Jonsson, A.K. Lundberg and L. Jonasson, PLoS One, 9, e105572 (2014); https://doi.org/10.1371/journal.pone.0105572
A. Yabluchanskiy, Y. Ma, R.P. Iyer, M.E. Hall and M.L. Lindsey, Physiology, 28, 391 (2013); https://doi.org/10.1152/physiol.00029.2013
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P. Little, BMJ, 368, m1185 (2020); https://doi.org/10.1136/bmj.m1185
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A. Capuano, C. Scavone, G. Racagni and F. Scaglione, Pharmacol. Res., 157, 104849 (2020); https://doi.org/10.1016/j.phrs.2020.104849
S. Wongrakpanich, A. Wongrakpanich, K. Melhado and J. Rangaswami, Aging Dis., 9, 143 (2018); https://doi.org/10.14336/AD.2017.0306
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Y. Wan, S. He, W. Li and Z. Tang, Anticancer Agents Med. Chem., 18, 1228 (2018); https://doi.org/10.2174/1871520618666180510113822
I. Denya, S.F. Malan and J. Joubert, Expert Opin. Ther. Pat., 28, 441 (2018); https://doi.org/10.1080/13543776.2018.1472240
H. Cerecetto, A. Gerpe, M. González, V.J. Arán and C.O. de Ocáriz, Mini Rev. Med. Chem., 5, 869 (2005); https://doi.org/10.2174/138955705774329564
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