Synthesis, antibacterial, antifungal and anti-HIV activities of Schiff and Mannich bases derived from isatin derivatives and N-[4-(4'-chlorophenyl)thiazol-2-yl] thiosemicarbazide.
Isatin, its 5-chloro and 5-bromo derivatives have been reacted with N-[4-(4'-chlorophenyl)thiazol-2-yl] thiosemicarbazide to form Schiff bases and the N-Mannich bases of these compounds were synthesized by reacting them with formaldehyde and three secondary amines. Their chemical structures have been confirmed by means of IR, 1H-NMR data and by elemental analysis. Investigation of antimicrobial activity of compounds was done by agar dilution method against 28 pathogenic bacteria, 8 pathogenic fungi and anti-HIV activity against replication of HIV-1 (IIIB) in MT-4 cells. Among the compounds tested 1-[N,N-dimethylaminomethyl]-5-bromo isatin-3-{1'-[4"-(p-chlorophenyl) thiazol-2"-yl] thio semicarbazone} 10 showed the most favourable antimicrobial activity.
Pandeya
S N
SN
Department Pharmaceutics, Institute of Technology, Banaras Hindu University, Varanasi, India. snpande@banaras.ernet.in
Sriram
D
D
Nath
G
G
DeClercq
E
E
D000900:Anti-Bacterial Agents; D019380:Anti-HIV Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D002478:Cells, Cultured; D003454:Cryptococcus / Q000187:drug effects; D015497:HIV-1 / Q000187:drug effects; D006801:Humans; D007510:Isatin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D008352:Mannich Bases / Q000138:chemical synthesis / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D012545:Schiff Bases / Q000138:chemical synthesis / Q000494:pharmacology*; D012663:Semicarbazides / Q000737:chemistry
D000900:Anti-Bacterial Agents; D019380:Anti-HIV Agents; D000890:Anti-Infective Agents; D000935:Antifungal Agents; D008352:Mannich Bases; D012545:Schiff Bases; D012663:Semicarbazides; C005151:thiosemicarbazide; D007510:Isatin