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Volume 79
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Article

Design, Synthesis and Biological Evaluation of New 5,5-Diarylhydantoin Derivatives as Selective Cyclooxygenase-2 Inhibitors

by
Afshin ZARGHI
1,*,
Farin SATTARY JAVID
1,
Razieh GHODSI
1,
Orkideh G. DADRASS
2,
Bahram DARAEI
3 and
Mehdi HEDAYATI
4
1
Department of Pharmaceutical Chemistry, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran
2
Department of Pharmaceutical Chemistry, School of Pharmacy, Azad University, Tehran, Iran
3
Department of Toxicology, Tarbiat Modarres University, Tehran, Iran
4
Research Institute for Endocrine Sciences, Shahid Beheshti University (M.C), Tehran, Iran
*
Author to whom correspondence should be addressed.
Sci. Pharm. 2011, 79(3), 449-460; https://doi.org/10.3797/scipharm.1104-20
Submission received: 25 April 2011 / Published: 25 July 2011
Versions Notes

Abstract

A new group of 5,5-diarylhydantoin derivatives bearing a methylsulfonyl COX-2 pharmacophore at the para position of the C-5 phenyl ring were designed and synthesized as selective COX-2 inhibitors. In vitro COX-1/COX-2 inhibition structure-activity relationships identified 5-[4-(methylsulfonyl)phenyl]-5-phenyl-hydantoin (4) as a highly potent and selective COX-2 inhibitor (COX-2 IC50 = 0.077 μM; selectivity index > 1298). It was more selective than the reference drug celecoxib (COX-2 IC50 = 0.060 μM; selectivity index = 405). A molecular modeling study where 4 was docked in the binding site of COX-2 indicated that the p-MeSO2 COX-2 pharmacophore group on the C-5 phenyl ring is oriented in the vicinity of the COX-2 secondary pocket. The results of this study showed that the type of substituent on the N-3 hydantoin ring substituent is important for COX-2 inhibitory activity.
Keywords: 5,5-Diarylhydantoin derivatives; COX-2 inhibition; Molecular modeling studies; SAR 5,5-Diarylhydantoin derivatives; COX-2 inhibition; Molecular modeling studies; SAR

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MDPI and ACS Style

ZARGHI, A.; SATTARY JAVID, F.; GHODSI, R.; DADRASS, O.G.; DARAEI, B.; HEDAYATI, M. Design, Synthesis and Biological Evaluation of New 5,5-Diarylhydantoin Derivatives as Selective Cyclooxygenase-2 Inhibitors. Sci. Pharm. 2011, 79, 449-460. https://doi.org/10.3797/scipharm.1104-20

AMA Style

ZARGHI A, SATTARY JAVID F, GHODSI R, DADRASS OG, DARAEI B, HEDAYATI M. Design, Synthesis and Biological Evaluation of New 5,5-Diarylhydantoin Derivatives as Selective Cyclooxygenase-2 Inhibitors. Scientia Pharmaceutica. 2011; 79(3):449-460. https://doi.org/10.3797/scipharm.1104-20

Chicago/Turabian Style

ZARGHI, Afshin, Farin SATTARY JAVID, Razieh GHODSI, Orkideh G. DADRASS, Bahram DARAEI, and Mehdi HEDAYATI. 2011. "Design, Synthesis and Biological Evaluation of New 5,5-Diarylhydantoin Derivatives as Selective Cyclooxygenase-2 Inhibitors" Scientia Pharmaceutica 79, no. 3: 449-460. https://doi.org/10.3797/scipharm.1104-20

APA Style

ZARGHI, A., SATTARY JAVID, F., GHODSI, R., DADRASS, O. G., DARAEI, B., & HEDAYATI, M. (2011). Design, Synthesis and Biological Evaluation of New 5,5-Diarylhydantoin Derivatives as Selective Cyclooxygenase-2 Inhibitors. Scientia Pharmaceutica, 79(3), 449-460. https://doi.org/10.3797/scipharm.1104-20

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