Synthesis and antiamoebic activities of 1-N-substituted cyclised pyrazoline analogues of thiosemicarbazones

A series of 21 new 1-N-substituted cyclised pyrazoline analogues of thiosemicarbazones were synthesised by cyclisation of Mannich bases with thiosemicarbazides of variegated nature. The chemical structures of the compounds were proved by UV, IR, 1H NMR, 13C NMR spectroscopic data and elemental analyses. The antiamoebic activities of these compounds were evaluated by microdilution method against HM1:1MSS strain of Entamoeba histolytica. It was found that 3-chloro and 3-bromo substituents on the phenyl ring at position 3 of the pyrazoline ring enhanced the antiamoebic activity as compared to unsubstituted phenyl ring. Compounds 15, 17, 18, 20 and 21 showed less IC50 value than metronidazole. Moreover, compound 21 have shown the most promising antiamoebic activity (IC50 = 0.6 μM vs IC50 = 1.8 μM of metronidazole).

A series of 21 new 1-N-substituted cyclised pyrazoline analogues of thiosemicarbazones were synthesised by cyclisation of Mannich bases with thiosemicarbazides of variegated nature. The antiamoebic activities of these compounds were evaluated by microdilution method against HM1:1MSS strain of Entamoeba histolytica. Compounds 15, 17, 18, 20 and 21 showed less IC50 value than metronidazole. Moreover, compound 21 have shown the most promising antiamoebic activity (IC50 = 0.6 μM vs IC50 = 1.8 μM of metronidazole).Figure optionsDownload as PowerPoint slide