Synthesis and cytotoxicity evaluation of naphthalenecarboxamide derivatives

Abstract

The core structure ethyl 4-acetoxy-6,8-dimethoxynaphthalene-2-carboxylate was successfully synthesized via a two step sequence including Stobbe condensation followed by cyclisation from 2,4-dimethoxybenzaldehyde as the starting material. The ethyl ester moiety was then hydrolyzed to form the corresponding carboxylic acid which was subsequently in situ converted to carboxyl chorides by reacting with thionyl chloride and then to carboxamides derivatives by treating with  4-methylbenzylamine and 3-morpholinopropylamine. The structures of the synthesized compounds were fully confirmed based on MS, 1H-NMR, 13C-NMR and DEPT spectroscopy data. Cytotoxicity evaluation showed that the two prepared napthalenecarboxamide derivatives had weak cytotoxicity against Lu cells and moderate cytotoxicity against Hep-G2 cell lines.