Abstract
The synthesis and pharmacological properties of 7-chloro-5-(2-chlorophenyl)-2-(2-dimethylaminoethylthio)-3H-1, 4-benzodiazepine (III-1) and related compounds are described. Compound III-1 was prepared from the thiolactam (II-1) by treatment with 2-dimethylaminoethyl chloride in the presence of base in aqueous methanol and 7-chloro-5-(2-ohlorophenyl)-2-methoxy-3H-1, 4-benzodiazepine (IV) was obtained as a by-product. The latter (IV) was hydrolyzed in acid medium to give methyl (E)-[2-amino-5-chloro-α-(2-chlorophenyl) benzylidene] aminoacetate (syn-form) (XIX), which was converted into the 1, 4-benzodiazepine (I-1) by further acid treatment. Compound XIX isomerized to the corresponding anti-form (XXII) on heating. Most of the compounds prepared had an effect similar to that of diazepam in causing taming and anticonvulsant effects in mice.
