Synthesis and antifilarial evaluation of 7-O-acetamidyl-4-alkyl-2H-1-benzopyran-2-ones

Arzneimittelforschung. 2003;53(12):857-63. doi: 10.1055/s-0031-1299841.

Abstract

A series of 7-O-acetamidyl-4-alkyl-2H-1-benzopyran-2-ones (5-23) has been synthesized by amidation of 7-O-(carbethoxymethyl)-4-alkyl-2H-1-benzopyran-2-ones (2a, 2b) with different primary and secondary amines in fair to good yield. The resulting compounds were screened for their filarial DNA topoisomerase inhibitory activity under in vivo condition in Setaria cervi. The compounds were tested in vitro against Brugia malayi. A few of the compounds possess promising antifilarial activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetamides / chemical synthesis*
  • Acetamides / therapeutic use*
  • Animals
  • Benzopyrans / chemical synthesis*
  • Benzopyrans / therapeutic use*
  • Brugia malayi / drug effects
  • Chemical Phenomena
  • Chemistry, Physical
  • Enzyme Inhibitors / pharmacology
  • Female
  • Filaricides / chemical synthesis*
  • Filaricides / therapeutic use*
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Setaria Nematode / drug effects
  • Spectrometry, Mass, Fast Atom Bombardment
  • Spectrophotometry, Infrared
  • Structure-Activity Relationship
  • Topoisomerase II Inhibitors

Substances

  • Acetamides
  • Benzopyrans
  • Enzyme Inhibitors
  • Filaricides
  • Indicators and Reagents
  • Topoisomerase II Inhibitors