Synthetic studies of vitamin D analogues. IX. Synthesis and differentiation-inducing activity of 1 alpha,25-dihydroxy-23-oxa-, thia-, and azavitamin D3.
Three vitamin D3 analogues, 1 alpha,25-dihydroxy-23-oxavitamin D3 (3), 1 alpha,25-dihydroxy-23-thiavitamin D3 (4) and 1 alpha,25-dihydroxy-23-azavitamin D3 (5) were synthesized. In the differentiation-inducing activity of human myeloid leukemia cells into macrophages in vitro, the 23-aza analogue (5) showed the least activity, while no remarkable differences were observed between the 23-oxa analogue (3) and the 23-thia analogue (4), which were less active than 1 alpha,25-dihydroxyvitamin D3 (1).
Kubodera
N
N
Exploratory Research Laboratories, Chugai Pharmaceutical Co., Ltd., Shizuoka, Japan.
Miyamoto
K
K
Akiyama
M
M
Matsumoto
M
M
Mori
T
T
D002117:Calcitriol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D002454:Cell Differentiation / Q000187:drug effects*; D013268:Stimulation, Chemical; D014407:Tumor Cells, Cultured; D014807:Vitamin D / Q000031:analogs & derivatives*
C074473:1,25-dihydroxy-23-oxavitamin D3; D014807:Vitamin D; C074477:1,25-dihydroxy-23-azavitamin D3; C074474:1,25-dihydroxy-23-thiavitamin D3; D002117:Calcitriol