Synthesis of 3,5-disubstituted pyridines as antimicrobial agents.
3,5-Diacetylpyridine (1) reacted with hydroxylamine hydrochloride, thiourea or phenylhydrazine affording the corresponding carbaldoximo- (2) aminothiazolyl-(3) and phenylhydrazono- (4) derivatives, respectively. Cyclization of 4 by the action of PPA or thionyl chloride afforded the corresponding indolyl- (5) and thiadiazolyl-(6) derivatives. Condensation of 1 with aldehydes yielded bis-(beta-acryloyl) derivatives 7, which on further treatment with malononitrile or ethyl cyanoacetate afforded cyanopyridines of the types 8 and 9. The latter was successfully utilized in the synthesis of thieno[2,3-b]pyridines 13. Some of the obtained compounds showed remarkable antimicrobial activity comparable to oxytetracycline.
Attia
A
A
Department of Applied Organic Chemistry, National Research Centre, Dokki, Cairo, Egypt.
Abo-Ghalia
M H
MH
Abd el-Salam
O I
OI
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D005658:Fungi / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D010118:Oxytetracycline / Q000494:pharmacology; D011725:Pyridines / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D015003:Yeasts / Q000187:drug effects
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D011725:Pyridines; D010118:Oxytetracycline