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Volume 76
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Article

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

by
Afshin ZARGHI
1,*,
Azar TAHGHIGHI
1,
Zohreh SOLEIMANI
1,
Bahram DARAIE
2,
Orkideh Gorban DADRASS
3 and
Mehdi HEDAYATI
4
1
Department of Medicinal Chemistry, School of Pharmacy, Shahid Beheshti University (M.C), P.O. Box: 14155-6153,Tehran, Iran
2
Department of Toxicology, School of Medical Sciences, Tarbiat Modares University, Tehran, Iran
3
School of Pharmacy, Azad University, Tehran, Iran
4
Endocrine research center, Shahid Beheshti University (M.C),Tehran, Iran
*
Author to whom correspondence should be addressed.
Sci. Pharm. 2008, 76(3), 361-376; https://doi.org/10.3797/scipharm.0805-20
Submission received: 27 May 2008 / Accepted: 7 July 2008 / Published: 8 July 2008
Versions Notes

Abstract

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

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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. https://doi.org/10.3797/scipharm.0805-20

AMA Style

ZARGHI A, TAHGHIGHI A, SOLEIMANI Z, DARAIE B, DADRASS OG, HEDAYATI M. Design and Synthesis of Some 5-Substituted-2-(4-(azido or methylsulfonyl)phenyl)-1H-indole Derivatives as Selective Cyclooxygenase (COX-2) Inhibitors. Scientia Pharmaceutica. 2008; 76(3):361-376. https://doi.org/10.3797/scipharm.0805-20

Chicago/Turabian Style

ZARGHI, Afshin, Azar TAHGHIGHI, Zohreh SOLEIMANI, Bahram DARAIE, Orkideh Gorban DADRASS, and Mehdi HEDAYATI. 2008. "Design and Synthesis of Some 5-Substituted-2-(4-(azido or methylsulfonyl)phenyl)-1H-indole Derivatives as Selective Cyclooxygenase (COX-2) Inhibitors" Scientia Pharmaceutica 76, no. 3: 361-376. https://doi.org/10.3797/scipharm.0805-20

APA Style

ZARGHI, A., TAHGHIGHI, A., SOLEIMANI, Z., DARAIE, B., DADRASS, O. G., & HEDAYATI, M. (2008). Design and Synthesis of Some 5-Substituted-2-(4-(azido or methylsulfonyl)phenyl)-1H-indole Derivatives as Selective Cyclooxygenase (COX-2) Inhibitors. Scientia Pharmaceutica, 76(3), 361-376. https://doi.org/10.3797/scipharm.0805-20

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