Synthetic studies of vitamin D analogues. XI. Synthesis and differentiation-inducing activity of 1 alpha,25-dihydroxy-22-oxavitamin D3 analogues.
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.
Kubodera
N
N
Exploratory Research Laboratories, Chugai Pharmaceutical Co., Ltd., Shizuoka, Japan.
Watanabe
H
H
Kawanishi
T
T
Matsumoto
M
M
D000818:Animals; D002117:Calcitriol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D002454:Cell Differentiation / Q000187:drug effects; D002642:Chick Embryo; D002762:Cholecalciferol / Q000138:chemical synthesis* / Q000494:pharmacology; D007422:Intestines / Q000187:drug effects; D013481:Superoxides / Q000032:analysis; D014407:Tumor Cells, Cultured
D013481:Superoxides; D002762:Cholecalciferol; D002117:Calcitriol; C051883:maxacalcitol