Synthesis and cytotoxicity of two novel alcohols based on a benzo[c]phenanthrene moiety

Synthetically, 1-(benzoc]phenanthren-2-yl)ethanol and 1-(benzoc]phenanthren-2-yl)-3-phenylpropane-1,3-diol were successfully obtained from 2-acetylbenzoc]phenanthrene and methyl benzoc]phenanthrene-2-carboxylate, respectively, and fully characterized. The desired compounds were purified by silica gel column chromatography, and their structures were characterized by melting points, ¹H NMR, ¹³C NMR, and mass spectroscopy. Next, the in vitro cytotoxicity of the new polyaromatic alcohols was evaluated against two human carcinoma cell lines (Hep-2 and Caco-2) using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay method. Consequently, the 1,3-diol derivative displayed the highest cytotoxicity against both cell lines (IC₅₀ = 0.7 and 0.6 μg/mL). This allowed us to infer that the effect of intramolecular hydrogen bond seems to be important for the cytotoxic activity.