Synthesis and anti-inflammatory activity evaluation of novel triazolyl-isatin hybrids

Sharma, Pramod K., Balwani, Sakshi, Mathur, Divya, Malhotra, Shashwat, Singh, Brajendra K., Prasad, Ashok K., Len, Christophe, Van der Eycken, Erik V., Ghosh, Balaram, Richards, Nigel G. J. ORCID: https://orcid.org/0000-0002-0375-0881 and Parmar, Virinder S. 2016. Synthesis and anti-inflammatory activity evaluation of novel triazolyl-isatin hybrids. Journal of Enzyme Inhibition and Medicinal Chemistry 31 (6) , pp. 1520-1526. 10.3109/14756366.2016.1151015

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Abstract

New isatin-triazole based hybrids have been synthesized and evaluated for their inhibitory activity of TNF-α induced expression of Intercellular Adhesion Molecule-1 (ICAM-1) on the surface of human endothelial cells. Structure-activity relationship (SAR) studies revealed that the presence of the electron-attracting bromo substituent at position-5 of the isatin moiety played an important role in enhancing the anti-inflammatory potential of the synthesized compounds. Z-1-[3-(1H-1,2,4-Triazol-1-yl)propyl]-5-bromo-3-[2-(4-methoxyphenyl)hydrazono]indolin-2-one (19) with an IC50 = 20 μM and 89% ICAM-1 inhibition with MTD at 200 μM was found to be the most potent of all the synthesized derivatives. Introduction of 1,2,4-triazole ring and electron-donating methoxy group on the phenylhydrazone moiety resulted in four-fold increase of the anti-inflammatory activity

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Subjects:	Q Science > QD Chemistry
Uncontrolled Keywords:	1,2,4-Triazole, anti-inflammatory activity, ICAM-1, isatin, triazolylisatins
Publisher:	Informa Healthcare
ISSN:	1475-6366
Date of Acceptance:	28 January 2016
Last Modified:	01 Nov 2022 10:17
URI:	https://orca.cardiff.ac.uk/id/eprint/90950

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