Design, synthesis and anticonvulsant activity of some new 5,7-dibromoisatin semicarbazone derivatives

Abstract

A series of 5,7-dibromoisatin semicarbazones have been synthesized in good yield, involving aryl urea and aryl semicarbazide formation. The structures of the synthesized compounds were confirmed on the basis of their spectral data. All the compounds were evaluated for anticonvulsant and CNS depressant activities. Anticonvulsant activity was determined after intraperitoneal (i.p.) administration to mice by maximal electroshock (MES) induced seizure method and minimal motor impairment was determined by rotarod test. A computational study was carried out for prediction of pharmacokinetic properties and making them potentially promising agents for the treatment of epilepsy. Compounds (Z)-1-(5,7-dibromo-2-oxoindolin-3-ylidene)-4-(4-chlorophenyl)semicarbazide (DH-05), (Z)-1-(5,7-dibromo-2-oxoindolin-3-ylidene)-4-(3-chloro-4-fluorophenyl)semicarbazide (DH-11) and (Z)-1-(5,7-dibromo-1-methyl-2-oxoindolin-3-ylidene)-4-(3-chloro-4-fluorophenyl)semicarbazide (DH-12) exhibited prominent anticonvulsant effect in the series with little or no neurotoxicity and little CNS depressant effect as compared to standard drug.