Synthesis and anti-inflammatory structure-activity relationships of thiazine-quinoline-quinones: inhibitors of the neutrophil respiratory burst in a model of acute gouty arthritis

Bioorg Med Chem. 2008 Nov 1;16(21):9432-42. doi: 10.1016/j.bmc.2008.09.052. Epub 2008 Sep 20.

Abstract

Sixteen new thiazine-quinoline-quinones have been synthesised, plus one bicyclic analogue. These compounds inhibited neutrophil superoxide production in vitro with IC(50)s as low 60 nM. Compounds with high in vitro anti-inflammatory activity were also tested in a mouse model of acute inflammation. The most active compounds inhibited both neutrophil infiltration and superoxide production at doses 2.5 micromol/kg, highlighting their potential for development as novel NSAIDs.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis*
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
  • Arthritis, Gouty / drug therapy*
  • Arthritis, Gouty / metabolism
  • Cell Proliferation / drug effects
  • Disease Models, Animal*
  • HL-60 Cells
  • Humans
  • Inflammation / drug therapy*
  • Inflammation / metabolism
  • Male
  • Mice
  • Mice, Inbred C57BL
  • Neutrophils / drug effects*
  • Quinolines / chemistry
  • Quinones / chemistry
  • Respiratory Burst / drug effects*
  • Structure-Activity Relationship
  • Superoxides / metabolism
  • Thiazines / chemistry

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Quinolines
  • Quinones
  • Thiazines
  • Superoxides
  • quinoline