A new benzo[c]phenanthrene ketone has been synthesized through Heck coupling and oxidative photocyclization. The optical properties of the target tetracyclic system were also investigated by UV-visible absorption and photoluminescence spectroscopy and an emission in the visible region was observed. The tetracyclic ketone has been reacted with primary amines in the presence of Lewis acid followed by NaBH4 reduction to provide new polyaromatic secondary amines in good yields and purity. All the synthesized new compounds were identified and characterized through a combination of nuclear magnetic resonance spectroscopy and mass spectrometric methods. The cytotoxic activity of all pure benzo[c]phenanthrene derivatives has been evaluated against Hep-2 cell line using (MTT) colorimetric assay.
Synthetically, 1-(benzo[c]phenanthren-2-yl)ethanol and 1-(benzo[c]phenanthren-2-yl)-3phenylpropane-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)-2,5diphenyltetrazolium bromide (MTT) assay method. Consequently, the 1,3-diol derivative displayed the highest cytotoxicity against both cell lines (IC 50 ¼ 0.7 and 0.6 mg/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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