CHEMICAL MODIFICATION OF NAFTALINE-1-IL-BIS(SODIUM CARBAMODITHIOATE)

Abstract

Introduction. Interest in numerous naphthylamine derivatives is due to a wide range of their biological activity (growth-stimulating, antimicrobial, anticancer, antiviral, antihypertensive, antidiabetic, etc.). The aim of the workis the synthesis of biologically active N,S,O-containing substances in the series of acetylenic, alkoxy- and aroxyalkyl esters of naphthylamine. Study of acylation, propargylation and alkylation reactions of naphthalene-1-yl-bis(sodium carbamodiothioate). Methodology. New derivatives of naphthylbisdithiocarbamic acid were synthesized as a result of the modification of disubstituted α-naphthylaminedithiocarbamate. It was shown that the interaction of α-naphthylaminebisdithiocarbamate with benzoic acid chloride, propargyl bromide and alkyl halides (2-methoxyethyl, 2-ethoxyethyl, 2-phenoxyethyl, 3-phenoxypropyl) leads to the formation of the corresponding thioanhydride, dithioacetylenic, alkoxy- and aroxyalkyl esters of naphthylbisdithiocarbamic acid. Synthesis was carried out in acetone at room temperature for 1.5 – 3 h. Reaction coursewas monitored by TLC method. Results and discussion. It was established that propargylation, acylation and alkylation reactions of α-naphthylaminedithiocarbamine derivative proceed easily and with high yields (66 − 91%). The structure of the synthesized compounds was established based on the data of elemental analysis and ¹H and ¹³C NMR spectroscopy. Thus, were synthesized new potentially biologically active naphthylbisdithiocarbamic acid derivatives, combining pharmacophore groups in their structure.