Design and synthesis of 3-alkyl-2-aryl-1,3-thiazinan-4-one derivatives as selective cyclooxygenase (COX-2) inhibitors

Tannaz Zebardast; Afshin Zarghi; Bahram Daraie; Mehdi Hedayati; Orkideh G Dadrass

doi:10.1016/j.bmcl.2009.04.125

Design and synthesis of 3-alkyl-2-aryl-1,3-thiazinan-4-one derivatives as selective cyclooxygenase (COX-2) inhibitors

Bioorg Med Chem Lett. 2009 Jun 15;19(12):3162-5. doi: 10.1016/j.bmcl.2009.04.125. Epub 2009 May 3.

Authors

Tannaz Zebardast¹, Afshin Zarghi, Bahram Daraie, Mehdi Hedayati, Orkideh G Dadrass

Affiliation

¹ Department of Pharmaceutical Chemistry, School of Pharmacy, Shahid Beheshti University (M.C), Tehran, Iran.

PMID: 19447036
DOI: 10.1016/j.bmcl.2009.04.125

Abstract

A new group of 3-alkyl-2-aryl-1,3-thiazinan-4-ones, possessing a methylsulfonyl pharmacophore, were synthesized and their biological activities were evaluated for cyclooxygenase-2 (COX-2) inhibitory activity. In vitro COX-1/COX-2 inhibition studies identified 3-benzyl-2-(4-methylsulfonylphenyl)-1,3-thiazinan-4-one (11a) as a potent (IC(50)=0.06 microM) and selective (selectivity index >285) COX-2 inhibitor.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Anti-Inflammatory Agents, Non-Steroidal / adverse effects
Anti-Inflammatory Agents, Non-Steroidal / chemistry
Cyclooxygenase 2 Inhibitors / chemical synthesis
Cyclooxygenase 2 Inhibitors / chemistry*
Cyclooxygenase 2 Inhibitors / pharmacology
Drug Design
Inhibitory Concentration 50
Mice
Structure-Activity Relationship
Thiazines / chemical synthesis
Thiazines / chemistry*
Thiazines / pharmacology

Substances

Anti-Inflammatory Agents, Non-Steroidal
Cyclooxygenase 2 Inhibitors
Thiazines