Synthesis and reactions of some delta beta,gamma-butenolides with a study of their biological activity

Pharmazie. 1988 Feb;43(2):80-1.

Abstract

alpha-(2-Thienylidene)-gamma-aryl-delta beta,gamma-butenolides 1 are prepared by condensing thiophene-2-aldehyde with beta-aroylpropionic acids in sodium acetate-acetic anhydride mixture. The butenolides react with ammonia in ethanol to give the corresponding 5-oxo-2-pyrrolines 2. Hydrazine hydrate reacts with the butenolides 1 with the formation of the corresponding acrylic acid hydrazides 3. Ring closure of the latter hydrazides with hydrochloric/acetic acid mixture gives the pyridazinones 4. The biological activity of the synthesized compounds is tested against bacterial and yeast strains. The butenolides 1 and the oxopyrrolines 2 inhibit the growth of yeast and gram-negative strain. The hydrazides 3 and the pyridazinones 4 are effective on gram-positive strains.

MeSH terms

  • 4-Butyrolactone / analogs & derivatives
  • Anti-Bacterial Agents
  • Anti-Infective Agents / chemical synthesis*
  • Anti-Infective Agents / pharmacology
  • Bacteria / drug effects
  • Chemical Phenomena
  • Chemistry
  • Furans / chemical synthesis*
  • Furans / pharmacology
  • Microbial Sensitivity Tests
  • Yeasts / drug effects

Substances

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Furans
  • butenolide
  • 4-Butyrolactone