Chemical and Pharmaceutical Bulletin · 1992 · 41 citations · 0 references
MedicineMedicinal ChemistryPharmacologyBiochemical PharmacologyMolecular PharmacologyStructure-activity RelationshipsLigand BindingStructure-activity Relationship AnalysisVitamin ChemistryVitamin DVitamin D MetabolismActivitiesVitamin AnaloguesVitamin D AnalogsVitamin D AnaloguesVitamin D MetabolitesVitamin D PhysiologyVitamin D ReceptorsVitamin D Synthesis
Six analogues of 1 alpha,25-dihydroxy-22-oxavitamin D3 (OCT) (2), 26,27-dimethyl OCT (5), 26,27-diethyl OCT (6), 24-norOCT (7), 24-homoOCT (8), 24-dihomoOCT (9), and 24-trihomoOCT (10) were synthesized from the 20(S)-alcohol (11) as the common starting material. In the activity inducing differentiation of human myeloid leukemia cells (HL-60) into macrophages, 26,27-dimethyl OCT (5) and 24-homoOCT (8) showed the highest activities. The binding properties of these analogues to the chick embryonic intestinal 1 alpha,25-dihydroxyvitamin D3 (1) receptor are also described.