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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