Synthesis and reactions of some delta beta,gamma-butenolides with a study of their biological activity.
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.
el-Kousy
S M
SM
Chemistry Department, Faculty of Science, Menoufia University, Shebin El-Kom, A.R.E.
el-Torgoman
A M
AM
el-Basiouny
A A
AA
Hashem
A I
AI
D015107:4-Butyrolactone / Q000031:analogs & derivatives; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D055598:Chemical Phenomena; D002621:Chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D015003:Yeasts / Q000187:drug effects
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D005663:Furans; C004511:butenolide; D015107:4-Butyrolactone