Next Article in Journal
Topological Models for Prediction of Pharmacokinetic Parameters of Cephalosporins using Random Forest, Decision Tree and Moving Average Analysis
Previous Article in Journal
Virtual Screening: A Fast Tool for Drug Design
Article Menu

Article Versions

Export Article

Scientia Pharmaceutica is published by MDPI from Volume 84 Issue 3 (2016). Articles in this Issue were published by another publisher in Open Access under a CC-BY (or CC-BY-NC-ND) licence. Articles are hosted by MDPI on as a courtesy and upon agreement with Austrian Pharmaceutical Society (Österreichische Pharmazeutische Gesellschaft, ÖPhG).
Open AccessArticle
Sci. Pharm. 2008, 76(3), 361-376; (registering DOI)

Design and Synthesis of Some 5-Substituted-2-(4-(azido or methylsulfonyl)phenyl)-1H-indole Derivatives as Selective Cyclooxygenase (COX-2) Inhibitors

Department of Medicinal Chemistry, School of Pharmacy, Shahid Beheshti University (M.C), P.O. Box: 14155-6153,Tehran, Iran
Department of Toxicology, School of Medical Sciences, Tarbiat Modares University, Tehran, Iran
School of Pharmacy, Azad University, Tehran, Iran
Endocrine research center, Shahid Beheshti University (M.C),Tehran, Iran
Author to whom correspondence should be addressed.
Received: 27 May 2008 / Accepted: 7 July 2008 / Published: 8 July 2008
PDF [204 KB, uploaded 28 December 2016]


A group of 5-substituted-2-(4-azido or (methylsulfonyl)phenyl)-1H-indoles were designed and synthesized as selective cyclooxygenase (COX-2) inhibitors. In vitro COX-1 and COX-2 isozyme inhibition studies were carried out to investigate the effect of different substituents (H, F, Cl, Me, OMe) at C-5 position and different pharmacophore groups (azido or methylsulfonyl) at para position of phenyl ring at C-2 position of the 1H-indole ring on COX-2 selectivity and potency. The structure-activity relationship study of these compounds indicated that the introduction of a methoxy substituent at C-5 position and 4-(methylsulfonyl) phenyl group at C-2 position of the 1H-indole ring (compound 4e) had the best COX-2 selectivity (S.I= 291.2). A molecular modeling study where 4e was docked in the binding site of COX-2 showed that the methylsulfonyl group at para position of phenyl ring is oriented in the vicinity of the COX-2 secondary pocket.
Keywords: 2-Phenyl-1H-indoles; COX-2 inhibitors; SAR 2-Phenyl-1H-indoles; COX-2 inhibitors; SAR
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

Share & Cite This Article

MDPI and ACS Style

ZARGHI, A.; TAHGHIGHI, A.; SOLEIMANI, Z.; DARAIE, B.; DADRASS, O.G.; HEDAYATI, M. Design and Synthesis of Some 5-Substituted-2-(4-(azido or methylsulfonyl)phenyl)-1H-indole Derivatives as Selective Cyclooxygenase (COX-2) Inhibitors. Sci. Pharm. 2008, 76, 361-376.

Show more citation formats Show less citations formats

Article Metrics

Article Access Statistics



[Return to top]
Sci. Pharm. EISSN 2218-0532 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top