Jr. Dimmock et al., SYNTHESIS AND CYTOTOXIC EVALUATION OF MESNA ADDUCTS OF SOME -ARYL-4,4-DIMETHYL-5-(1-PIPERIDINO)-1-PENTEN-3-ONE HYDROCHLORIDES, Die Pharmazie, 50(7), 1995, pp. 449-453
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.