Abstract
Synthetically, 1-(benzo[ c ]phenanthren-2-yl)ethanol and 1-(benzo[ c ]phenanthren-2-yl)-3-phenylpropane-1,3-diol were successfully obtained from 2-acetylbenzo[ c ]phenanthrene and methyl benzo[ c ]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, 1 H NMR, 13 C 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 (IC 50 = 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.
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