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

Year: 2016
Type: article
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.
DOI: 10.3109/14756366.2016.1151015
Authors: Pramod K. Sharma, Sakshi Balwani, Divya Mathur, Shashwat Malhotra, Brajendra K. Singh, Ashok K. Prasad, Christophe Len, Erik V. Van der Eycken, Balaram Ghosh, Nigel G. J. Richards, Virinder S. Parmar
Institutions: University of Delhi, Wockhardt (India), Institute of Genomics and Integrative Biology, Université de Technologie de Compiègne, University of Hull, École Supérieure de Chimie Organique et Minérale, KU Leuven, Indiana University – Purdue University Indianapolis, Cardiff University
Language: English
Field: Chemistry
Open Access status: bronze
OpenAlex ID: W2346633429
FWCI: 1.375
Cites: 41
Cited by: 83
Related to: 10