Synthesis and Biological Evaluation of Enantioenriched Phenols Having an Isobornyl Substituent

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

Journal Name: Letters in Organic Chemistry

Volume 8 , Issue 5 , 2011

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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.

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

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Article Details

Year: 2011
Page: [301 - 308]
Pages: 8
DOI: 10.2174/157017811795685054
Price: $65

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