Synthesis and antiproliferative evaluation of some 1,4-naphthoquinone derivatives against human cervical cancer cells

Abstract

In the course of biological properties of quinone derivatives, the N(H)-, S- and S,S-substituted-1,4-naphthoquinones were synthesized by reactions of 2,3-dichloro-1,4-naphthoquinone with different amines (2-morpholinoaniline, tert-butyl 4-aminobenzoate, 4-tert-butylbenzylamine, N-(3-aminopropyl)-2-pipecoline, 2-amino-5,6-dimethylbenzothiazole, N,N'-diphenyl-p-phenylenediamine) and thiolat (sodium 2-methyl-2-propanethiolate). All new products were characterized by MS-ESI, UV-Vis, FT-IR, 1H NMR, 13C NMR. The antiproliferative activities of these compounds on human cervical cancer (HeLa) cells were evaluated by MTT (3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyl tetrazolium bromide) assay. Although all derivatives inhibited cell growth, the most active compound was 2-(tert-butylthio)-3-chloronaphthalene-1,4-dione 5 (IC50=10.16 μM) against the HeLa cells.

Keywords

• quinones
• amines
• thiols
• antiproliferative activity
• hela cell