Successive paired electrochemical synthesis as a green strategy for late-stage modification of flutamide an anti-cancer drug. Gram-scale synthesis and antibacterial activity

•Late-stage modification of drugs.•Electrochemical synthesis of flutamide derivatives.•Successive paired electrochemical synthesis.•Gram-scale synthesis.•Antibacterial activity of flutamide derivatives. The late-stage modification of drugs (LSMD) has always been of interest due to their more promising activity than the original drug. Therefore, in this research, new flutamide derivatives have been synthesized through the electrolysis of flutamide in the presence of arylsulfinic acids or barbituric acids as nucleophiles, via a successive paired electrochemical method. The results indicate that flutamide is converted to the desired product after successive reduction and oxidation at electrodes and reaction with a nucleophile. This strategy led to the successful synthesis of new flutamide derivatives under facile conditions, without the need for catalyst or oxidant/reductant agents, in gram-scale quantity. The synthesized compounds were tested for antibacterial activity. The results confirmed that some flutamide derivatives show promising antibacterial activity. The late-stage modification (LSM) of flutamide was performed in the presence of arylsulfinic acids or barbituric acids as nucleophiles through a successive paired electrochemical strategy. This strategy led to the successful synthesis of new flutamide derivatives under facile conditions, without the need for catalyst or oxidant/reductant agents, in gram-scale quantity. [Display omitted]