Letters in Organic Chemistry · 2011 · 24 citations · 0 references
Pharmaceutical ScienceChemoprevention StrategyOrganic ChemistryPharmacotherapyPharmaceutical ChemistryMolecular PharmacologyMedicinal ChemistryBiological EvaluationAnti-cancer AgentStereoselective SynthesisRadiation OncologyX-ray Diffraction AnalysisInhibitory ActivityBiochemistryEnantioenriched PhenolsSeparated PhenolsDrug DevelopmentNatural Product SynthesisPharmacologyAsymmetric CatalysisEnantioselective SynthesisBiomolecular EngineeringIsobornyl SubstituentNatural SciencesMedicineDrug Discovery
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.