Synthesis and evaluation of pyrazolines bearing benzothiazole as anti-inflammatory agents

被引：82

作者：

Kharbanda, Chetna ^{[1
]}

Alam, Mohammad Sarwar ^{[1
]}

Hamid, Hinna ^{[1
]}

Javed, Kalim ^{[1
]}

Bano, Sameena ^{[1
]}

Dhulap, Abhijeet ^{[2
]}

Ali, Yakub ^{[1
]}

Nazreen, Syed ^{[1
]}

Haider, Saqlain ^{[1
]}

机构：

[1] Hamdard Univ, Fac Sci, Dept Chem, New Delhi 110062, India

[2] CSIR, Unit Res & Dev Informat Prod, Pune 411038, Maharashtra, India

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2014年 / 22卷 / 21期

关键词：

Pyrazolines; Anti-inflammatory; COX-2; TNF-alpha; Molecular docking; BIOLOGICAL EVALUATION; BENZENE SULFONAMIDE; INVOLVEMENT; DERIVATIVES; ANTICANCER;

D O I：

10.1016/j.bmc.2014.09.028

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：

The present study aims at the synthesis of pyrazolines bearing benzothiazole and their evaluation as anti-inflammatory agents. The synthesized compounds were evaluated for their anti-inflammatory potential using carrageenan induced paw edema model. Two compounds 5a and 5d alleviated inflammation more than the standard drug celecoxib. Eight compounds 5b, 5c, 5e, 5g, 5h, 6b, 6e and 6f showed anti-inflammatory activity comparable to celecoxib. To understand the mode of action, COX-2 enzyme assay and TNF-alpha assay were carried out. All the active compounds were assessed for their cytotoxicity. The ulcerogenic risk evaluation was performed on the active compounds that were not found to be cytotoxic. Out of ten active compounds, two compounds (5d and 6f) were finally found to be the most potent anti-inflammatory agents attributing to the suppression of the COX-2 enzyme activity and TNF-alpha production without being either cytotoxic or ulcerogenic. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：5804 / 5812

页数：9

共 46 条

[1]

[Anonymous], 2011, LIGPREP VERS 2 5

[2] Synthesis and biological evaluation of some new 2-pyrazolines bearing benzene sulfonamide moiety as potential anti-inflammatory and anti-cancer agents [J].

Bano, Sameena ;

Javed, Kalim ;

Ahmad, Shamim ;

Rathish, I. G. ;

Singh, Surender ;

Alam, M. S. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (12) :5763-5768

[3] Synthesis of some new 1,3,5-trisubstituted pyrazolines bearing benzene sulfonamide as anticancer and anti-inflammatory agents [J].

Bashir, Rafia ;

Ovais, Syed ;

Yaseen, Shafiya ;

Hamid, Hinna ;

Alam, M. S. ;

Samim, Mohammad ;

Singh, Surender ;

Javed, Kalim .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (14) :4301-4305

[4] Synthesis and Biological Evaluation of Novel Pyrazole Derivatives as Anti-Inflammatory Antimicrobial Agents [J].

Bekhit, Adnan A. ;

Ashour, Hayam M. A. ;

Bekhit, Alaa El-Din A. ;

Bekhit, Salma A. .

MEDICINAL CHEMISTRY, 2009, 5 (02) :103-117

[5] SULFONYLUREA RECEPTORS, ION CHANNELS, AND FRUIT-FLIES [J].

BOYD, AE .

DIABETES, 1988, 37 (07) :847-850

[6] Drug-like Bioactive Structures and Conformational Coverage with the LigPrep/ConfGen Suite: Comparison to Programs MOE and Catalyst [J].

Chen, I-Jen ;

Foloppe, Nicolas .

JOURNAL OF CHEMICAL INFORMATION AND MODELING, 2010, 50 (05) :822-839

[7] MECHANISM OF SELECTIVE-INHIBITION OF THE INDUCIBLE ISOFORM OF PROSTAGLANDIN G/H SYNTHASE [J].

COPELAND, RA ;

WILLIAMS, JM ;

GIANNARAS, J ;

NURNBERG, S ;

COVINGTON, M ;

PINTO, D ;

PICK, S ;

TRZASKOS, JM .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1994, 91 (23) :11202-11206

[8] Cyclooxygenase inhibitors - current status and future prospects [J].

Dannhardt, G ;

Kiefer, W .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2001, 36 (02) :109-126

[9] Drug discovery: A historical perspective [J].

Drews, J .

SCIENCE, 2000, 287 (5460) :1960-1964

[10] Role of cytokines in rheumatoid arthritis [J].

Feldmann, M ;

Brennan, FM ;

Maini, RN .

ANNUAL REVIEW OF IMMUNOLOGY, 1996, 14 :397-440

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