Synthesis, characterisation, and antineoplastic cytotoxicity of hybrid naphthohydroquinone–nucleic base mimic derivatives

Abstract

From a partially degraded Diels–Alder adduct of α-myrcene and 1,4-benzoquinone, several model compounds belonging to a new series of 1,4-naphthohydroquinone derivatives have been prepared. Phenyl, pyridyl, imidazolyl and some nucleic base mimic heterocycles have been attached to the naphthohydroquinone system through linkers of different size and type, leading to potentially antineoplastic hybrid structures. The new compounds have been evaluated in vitro for their cytotoxicity against cultured human cancer cells of A-549 lung carcinoma, HT-29 colon adenocarcinoma and MDA-MB-231 breast carcinoma. GI50 values ranged in the μM level.