Synthesis and characterization of thiosemicarbazones derived from enantiomers of 1-(2-NAPHTHYL) ethylamine

Thiosemicarbazones are compounds with a broad spectrum of antitumor action. In this study, twentysix novel chiral thiosemicarbazones, which are thought to have biologically positive lung cancer activities, were synthesized and their structures were characterized. The amine group in the structure of the 2-naphthylethylamine selected as the starting material was reacted with the 4-acetylbenzene sulfonyl chloride derivative in the presence of triethylamine in dichloromethane and converted to the amide group and chiral sulfonamides [S1, S2] were synthesized. Then, 4- substitutedphenyl thiosemicarbazide derivatives [T1-T13] obtained by the treatment of 4-substitutedphenyl isothiocyanates with hydrazine hydrate were reacted with the sulfonamide compound in methanolic medium to obtain thiosemicarbazone derivatives [1-26]. All reactions were monitored by TLC, and the products obtained are purified by crystallized from the appropriate solvent. Elemental analysis (CHNS), UV, IR, 1H NMR, 13C NMR, and mass spectroscopy were used to elucidate the structures of the new thiosemicarbazone derivatives.