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

Become EABM
Become Reviewer

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.

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

Rights & PermissionsPrintExport Cite as

Article Details

VOLUME: 8
ISSUE: 5
Year: 2011
Page: [301 - 308]
Pages: 8
DOI: 10.2174/157017811795685054
Price: $58

Article Metrics

PDF: 3