CHIRAL RESOLUTION OF THE ENANTIOMERS OF TETRAHYDRONAPHTHALENIC DERIVATIVES, NEW AGONIST AND ANTAGONIST LIGANDS FOR MELATONIN RECEPTORS, USING HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY ON CELLULOSE CHIRAL STATIONARY PHASES

Analytical HPLC methods using derivatized cellulose chiral stationary phases were developed for the separation of the enantiomers of methoxy and ethyl tetrahydronaphthalenic derivatives, new agonist and antagon ist ligands for melatonin receptors. The resolution were made using no rmal-phase methodology with a mobile phase consisting of n-hexane-alco hol (methanol, ethanol, 1-propanol or 2-propanol) in various percentag e, and a silica-based cellulose tris-3,5-dimethylphenylcarbamate (Chir alcel OD-H), or tris-methylbenzoate (Chiralcel OJ). The mobile phase a nd the chiral stationary phase were varied to achieve the best resolut ion. The effects of concentration of alcohol, various aliphatic alcoho ls in the mobile phase were studied. The effects of substitution were analysed. Baseline separation (R-s>1.5) was easily obtained in many ca ses. The resolution results were complementary between the two columns . (C) 1998 Elsevier Science B.V. All rights reserved.