Synthesis, antibacterial, antifungal and anti-HIV activities of Schiff andMannich 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 bee n confirmed by means of IR:H-1-NMR data and by elemental analysis. Investig ation of antimicrobial activity of compounds was done by agar dilution meth od against 28 pathogenic bacteria, 8 pathogenic fungi and anti-HIV activity against replication of HIV-I (IIIB) in MT-4 cells. Among the compounds tes ted 1-[N,N-dimethylaminomethyl]-5-bromo-isatin-3-{1'-[4 "-(p-chlorophenyl) thiazol-2 "-yl] thio semicarbazone} 10 showed the most favourable antimicro bial activity. (C) 1999 Elsevier Science B.V. All rights reserved.