Evaluation of some thiosemicarbazones of arylidene ketones and analogues for anticonvulsant activities

Article abstract of DOI:10.1016/0223-5234(90)90182-3

A number of thiosemicarbazones of arylidene and aryl ketones were prepared as candidate anticonvulsant agents.X-Ray crystallography of 4-(4-methylphenyl)-3-buten-2-one thiosemicarbazone (1a) revealed that it had the E configuration with respect to both olefinic and carbimino double bonds.Other structural features of this anticonvulsant compound were noted.Most of the compounds displayed activity in the MES and/or scMET tests and of particular interest was acetophenone thiosemicarbazone (4b) which had good activity when administered by the intraperitoneal and oral routes.High resolution 1H NMR spectroscopy of selected compounds in dimethylsulphoxide-d6 revealed that in most cases equilibrium was attained of mixtures of E and Z isomers pertaining to the stereochemistry of the carbimino group.In general this isomeric ratio was dependent on the size of the R group attached to the carbimino function.