6-Alkyl, alkoxy, or alkylthio-substituted 3-(4-methanesulfonylphenyl)-4-phenylpyran-2-ones: a novel class of diarylheterocyclic selective cyclooxygenase-2 inhibitors

Bioorg Med Chem Lett. 2003 Jul 7;13(13):2205-9. doi: 10.1016/s0960-894x(03)00391-3.

Abstract

A novel class of 3-(4-methanesulfonylphenyl)-4-phenylpyran-2-ones possessing a central six-membered lactone (pyran-2-one) ring system, in conjunction with C-6 alkyl (Me, Et or i-Pr), alkoxy (OMe, OEt or O-i-Pr), and alkylthio (SMe, SEt or S-i-Pr) substituents, were designed for evaluation as selective COX-2 inhibitors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkanes / chemical synthesis*
  • Alkanes / pharmacology*
  • Binding Sites / drug effects
  • Cyclooxygenase 1
  • Cyclooxygenase 2
  • Cyclooxygenase 2 Inhibitors
  • Cyclooxygenase Inhibitors / chemical synthesis*
  • Cyclooxygenase Inhibitors / pharmacology*
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / pharmacology*
  • Hydrogen Bonding
  • Indicators and Reagents
  • Isoenzymes / metabolism*
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Prostaglandin-Endoperoxide Synthases / metabolism*
  • Pyrones / chemical synthesis*
  • Pyrones / pharmacology*
  • Structure-Activity Relationship
  • Sulfones / chemical synthesis*
  • Sulfones / pharmacology*

Substances

  • Alkanes
  • Cyclooxygenase 2 Inhibitors
  • Cyclooxygenase Inhibitors
  • Heterocyclic Compounds
  • Indicators and Reagents
  • Isoenzymes
  • Pyrones
  • Sulfones
  • Cyclooxygenase 1
  • Cyclooxygenase 2
  • Prostaglandin-Endoperoxide Synthases