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

Add time:07/22/2019    Source:sciencedirect.com

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, 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.

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