Synthesis and Biological Evaluation of Enantioenriched Phenols Having an Isobornyl Substituent

Title: Synthesis and Biological Evaluation of Enantioenriched Phenols Having an Isobornyl Substituent

Volume: 8 Issue: 5

Author(s): Evgeny V. Buravlev, Irina Y. Chukicheva, Kyrill Y. Suponitsky, Yurii B. Vikharev, Victoria V. Grishko and Aleksandr V. Kutchin

Affiliation:

Keywords: Aminomethylation, anti-inflammatory activity, chiral auxiliaries, cytotoxicity, enantiomers, terpenylphenols, X-ray diffraction analysis, sulfonyl, camphanic chloride

Abstract: The resolution of 2-isobornyl-4-methylphenol (±)-1 via diastereomers was carried out. The enantioenriched phenols (+)-1, ( – )-1 and morpholinomethyl derivatives (+)-6, ( – )-6 were tested for their cytotoxic and anti-inflammatory activities in comparison with their racemates. The anti-inflammatory activity comparable to that of indomethacin estimated for the racemic amine (±)-6 is due to the enantiomer (+)-6. The enantiomer ( – )-6 exhibits a moderate cytotoxicity against the human cancer cell line melanoma (MS) while enantiomer ( – )-1 demonstrates the inhibitory activity against the human cancer cell line lung carcinoma (A549). The absolute configuration of the diastereomeric intermediates and separated phenols were established by X-ray diffraction analysis.

Cite this article as:

V. Buravlev Evgeny, Y. Chukicheva Irina, Y. Suponitsky Kyrill, B. Vikharev Yurii, V. Grishko Victoria and V. Kutchin Aleksandr, Synthesis and Biological Evaluation of Enantioenriched Phenols Having an Isobornyl Substituent, Letters in Organic Chemistry 2011; 8 (5) . https://dx.doi.org/10.2174/157017811795685054