SYNTHESIS AND CYTOTOXIC EVALUATION OF MESNA ADDUCTS OF SOME -ARYL-4,4-DIMETHYL-5-(1-PIPERIDINO)-1-PENTEN-3-ONE HYDROCHLORIDES

Reaction of enyl)-4,4-dimethyl-5-(1-piperidino)-1-penten-3-one hydroch loride (1f) with sodium 2-mercaptoethanesulphonate (mesna) gave rise t o the thiol adduct 3. Recrystallization of this compound led to the fo rmation of the corresponding zwitterion 4f. A series of analogues of 4 f were prepared and the structure of a representative compound was con firmed by X-ray crystallography. In general, the thiol adducts had sim ilar activity towards P388 cells and human tumour cell lines as the pr ecursor enones 1 although greater selectivity to malignant diseases wa s found with the thiol adducts. A stability study of representative co mpounds conducted by H-1 NMR spectroscopy revealed that the thiol addu cts decomposed in solution. In one case regeneration of the ketone was noted while for the other compounds, the decomposition products were not identified.