Synthesis and antimicrobial activity of thiosemicarbazides, s-triazoles and their Mannich bases bearing 3-chlorophenyl moiety.
A fast and efficient synthesis of some 1,4-disubstituted thiosemicarbazide derivatives is described. The reaction of 3-chlorobenzoic acid hydrazide with various aryl isothiocyanates gave thiosemicarbazide derivatives (1-11) in good yield. The cyclization of compounds (1-11) in the presence of 2% NaOH resulted in the formation of compounds (12-22) containing the 1,2,4-triazole ring. A series of new Mannich bases (23-33) related to the structure of 1,2,4-triazole has been also synthesized. All of these compounds were tested for their in vitro antibacterial activity against the reference strains of aerobic bacteria - 6 Gram-positive and 3 Gram-negative ones; 12 Staphylococcus aureus clinical isolates were also examined. An attempt was made to clarify the influence of the nature/position of substituents on antibacterial activity of compounds described.
Department of Organic Chemistry, Faculty of Pharmacy, Medical University, Staszica 6, 20-081 Lublin, Poland. tomasz.plech@umlub.pl
Tomasz
T
Plech
Monika
M
Wujec
Agata
A
Siwek
Urszula
U
Kosikowska
Anna
A
Malm
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D006801:Humans; D008352:Mannich Bases / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D012663:Semicarbazides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
D000900:Anti-Bacterial Agents; D008352:Mannich Bases; D012663:Semicarbazides; D014230:Triazoles; C005151:thiosemicarbazide