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

被引：65

作者：

Sharma, Pramod K. ^{[1
,2
]}

Balwani, Sakshi ^{[3
]}

Mathur, Divya ^{[1
,4
]}

Malhotra, Shashwat ^{[1
]}

Singh, Brajendra K. ^{[1
]}

Prasad, Ashok K. ^{[1
]}

Len, Christophe ^{[5
,6
]}

Van der Eycken, Erik V. ^{[7
]}

Ghosh, Balaram ^{[3
]}

Richards, Nigel G. J. ^{[8
,9
]}

Parmar, Virinder S. ^{[1
,5
,8
]}

机构：

[1] Univ Delhi, Dept Chem, Bioorgan Lab, Delhi 110007, India

[2] Wockhardt Res Ctr, Chem Res Lab, Aurangabad, Maharashtra, India

[3] CSIR, Immunogenet Lab, Inst Genom & Integrat Biol, Delhi, India

[4] Univ Delhi, Dept Chem, Daulat Ram Coll, Delhi, India

[5] UTC, ESCOM, Sorbonne Univ, Compiegne, France

[6] Univ Hull, Dept Chem, Kingston Upon Hull, N Humberside, England

[7] Univ Leuven KU Leuven, Dept Chem, LOMAC, Leuven, Belgium

[8] Indiana Univ Purdue Univ, Dept Chem & Chem Biol, Indianapolis, IN 46202 USA

[9] Cardiff Univ, Sch Chem, Coll Phys Sci & Engn, Cardiff, S Glam, Wales

来源：

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY | 2016年 / 31卷 / 06期

关键词：

1,2,4-Triazole; anti-inflammatory activity; ICAM-1; isatin; triazolylisatins; MANNICH-BASES; SCHIFF; DERIVATIVES; HYDRAZONES; DESIGN; ANTIBACTERIAL; ANTIFUNGAL; EXPRESSION; ANALOGS;

D O I：

10.3109/14756366.2016.1151015

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

New isatin-triazole based hybrids have been synthesized and evaluated for their inhibitory activity of TNF-alpha 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 mu M and 89% ICAM-1 inhibition with MTD at 200 mu M 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.

引用

页码：1520 / 1526

页数：7

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