Novel 6-methanesulfonamide-3,4-methylenedioxyphenyl-N-acylhydrazones: orally effective anti-inflammatory drug candidates

Bioorg Med Chem. 2009 Feb 1;17(3):1125-31. doi: 10.1016/j.bmc.2008.12.045. Epub 2008 Dec 25.

Abstract

We described herein the molecular design of novel in vivo anti-inflammatory 6-methanesulfonamide-3,4-methylenedioxyphenyl-N-acylhydrazone derivatives (1) planned by applying the molecular hybridization approach. This work also points out to the discovery of LASSBio-930 (1c) as a novel anti-inflammatory and anti-hyperalgesic prototype, which was able to reduce carrageenan-induced rat paw edema with an ED(50) of 97.8 micromol/kg, acting mainly as a non-selective COX inhibitor.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Administration, Oral
  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry*
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
  • Benzodioxoles / chemical synthesis
  • Benzodioxoles / chemistry*
  • Benzodioxoles / pharmacology*
  • Carrageenan / chemistry
  • Computer Simulation
  • Crystallography, X-Ray
  • Cyclooxygenase Inhibitors / metabolism
  • Disease Models, Animal
  • Edema / chemically induced
  • Edema / drug therapy
  • Edema / prevention & control
  • Female
  • Hydrazones / chemical synthesis
  • Hydrazones / chemistry*
  • Hydrazones / pharmacology*
  • Male
  • Rats
  • Rats, Wistar
  • Thermodynamics

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Benzodioxoles
  • Cyclooxygenase Inhibitors
  • Hydrazones
  • N-(6-((2-benzylidenehydrazinyl)carbonyl)-1,3-benzodioxol-5-yl)methanesulfonamide
  • Carrageenan