A powerful analgesic, anti-inflammatory and antimicrobial drug was developed by synthesizing a set of new indole-2,3-dione derivatives. The chemical structures of the synthesized derivatives were confirmed by spectroscopic and elemental analyses. Tail flick method, carrageenan-induced foot paw edema technique and agar streak dilution methods were employed to evaluate analgesic, anti-inflammatory and antimicrobial activities (in vitro) of drugs, respectively. In addition, ulcerogenicity of potent derivatives was also estimated. Most of the synthesized derivatives displayed low-to-reasonable ulcer index, with mild-togoodanalgesic, anti-inflammatory and antimicrobial potency. The SARs between the biological activity and differences in the functional group of the title compounds have been explained. 1-(4-Chlorobenzylidene)-4-(4-(1-((dimethylamino)methyl)-5-nitro-2-oxoindolin-3-ylideneamino)phenyl)thiosemicarbazide VIc has beenfound as the potent derivative of this series.