Bridged bis(4-thiazolidinones) and related compounds with antibacterial activity.
Condensation of 4,4'-diaminobiphenyl ether (1) and 4,4'-diaminobiphenyl methane (6) with various aldehydes gave diarylidenebiphenyl ethers 2a-d and diarylidenebiphenyl methanes 7a-c, respectively, which on cyclocondensation with merceptoacetic acid yielded 3,3'-[oxy-bis(4,1-phenylene)]-bis[(2-substituted phenyl)-4- thiazolidinones] 3a-d and 3,3'-[methylene-bis(4,1-phneylene)]-bis[2-substituted phenyl)-4-thiazolidinones] 8a-c. A series of 2,2'-[oxy-bis(4,1-phenylenenitrilo)]-bis[3- (substituted)-4-thiazolidinones] 5a and b and 2,2'-[methylene-bis(4,1-phnylenenitrilo)]-bis[3-(substituted)-4- thiazolidinones] 10a and b were synthesized from 4,4'-diaminobiphenyl ether (1) and 4,4'-diaminobiphenyl methane (6) via the corresponding dithiocarbamide biphenyl ethers 4a and b and dithiocarbamide biphenyl methanes 9a and b by cyclocondensation with monochloroacetic acid. The structures of compounds 2-10 are supported by elemental analysis and spectral data (IR, 1H NMR, 13C NMR). The specific rotation of compounds 3c, 8b and 8c was measured.
Pandya
D
D
Department of Chemistry, Faculty of Science, M.S. University of Baroda, India.
Nair
K B
KB
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000995:Antitubercular Agents / Q000138:chemical synthesis / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects*; D001952:Bridged-Ring Compounds / Q000737:chemistry* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D013844:Thiazoles / Q000737:chemistry* / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D000995:Antitubercular Agents; D001952:Bridged-Ring Compounds; D013844:Thiazoles