Collect. Czech. Chem. Commun. 1985, 50, 1498-1506

Synthesis of several compounds related to 1-(4-methylsulfonylphenacyl)-4-phenylpiperazine and their pharmacological screening

Zdeněk Vejdělek, Václav Bártl, Emil Svátek and Miroslav Protiva

Research Institute for Pharmacy and Biochemistry, 130 60 Prague 3


The title compound I was transformed to its oxime II, hydrazone III and semicarbazone IV. 1-(4-Methylsulfonylphenyl)-2-(4-phenylpiperazino)ethanol (V) was esterified by the corresponding acid chlorides in pyridine to give the acetate VI, propionate VII, benzoate VIII, and 4-nitrobenzoate IX. Reactions of 4-(methylsulfonyl)phenacyl bromide, its 4-(ethylsulfonyl), and 4-(2-methylpropylsulfonyl)analogues with diethanolamine afforded instead of the expected substitution products X the hemiacetals XI-XIII, i.e. 2-hydroxy-4-(2-hydroxyethyl)-2-(4-alkylsulfonylphenyl)morpholines. The products were subjected to the pharmacological and microbiological screening; compounds II-IV and VI-IX have more or less the character of tranquillizers, the hemiacetals XI-XIII have some antimicrobial activity in vitro. Compound XIII showed, surprisingly, a positively inotropic effect, and its methiodide XIV a peripheral myorelaxant effect.