Design and synthesis of new 1,3-benzthiazinan-4-one derivatives as selective cyclooxygenase (COX-2) inhibitors

Afshin Zarghi; Tannaz Zebardast; Bahram Daraie; Mehdi Hedayati

doi:10.1016/j.bmc.2009.06.056

Design and synthesis of new 1,3-benzthiazinan-4-one derivatives as selective cyclooxygenase (COX-2) inhibitors

Bioorg Med Chem. 2009 Aug 1;17(15):5369-73. doi: 10.1016/j.bmc.2009.06.056. Epub 2009 Jun 27.

Authors

Afshin Zarghi¹, Tannaz Zebardast, Bahram Daraie, Mehdi Hedayati

Affiliation

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

PMID: 19596198
DOI: 10.1016/j.bmc.2009.06.056

Abstract

A new group of 1, 3-benthiazinan-4-ones, possessing a methyl sulfonyl 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-(p-fluoropheny)-2-(4-methylsulfonylphenyl)-1,3-benzthiazinan-4-one (7b) as a potent (IC(50)=0.05 microM) and selective (selectivity index=259) COX-2 inhibitor.

Publication types

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

MeSH terms

Animals
Catalytic Domain
Cyclooxygenase 2 / chemistry
Cyclooxygenase 2 / metabolism*
Cyclooxygenase Inhibitors / chemical synthesis
Cyclooxygenase Inhibitors / chemistry*
Cyclooxygenase Inhibitors / pharmacology*
Drug Design
Models, Molecular
Molecular Structure
Murinae
Protein Binding
Structure-Activity Relationship
Thiazines / chemical synthesis
Thiazines / chemistry*
Thiazines / pharmacology*

Substances

1,3-benzthiazinan-4-one
Cyclooxygenase Inhibitors
Thiazines
Cyclooxygenase 2