Synthetic Studies of Vitamin D Analogues. IX. Synthesis and Differentiation-Inducing Activity of 1α, 25-Dihydroxy-23-oxa-, thia-, and azavitamin D3

Noboru KUBODERA; Katsuhito MIYAMOTO; Masashi AKIYAMA; Masahiko MATUMOTO; Takashi MORI

doi:10.1248/cpb.39.3221

Synthetic Studies of Vitamin D Analogues. IX. Synthesis and Differentiation-Inducing Activity of 1α, 25-Dihydroxy-23-oxa-, thia-, and azavitamin D₃

Noboru KUBODERA, Katsuhito MIYAMOTO, Masashi AKIYAMA, Masahiko MATUMOTO, Takashi MORI

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Keywords: vitamin D₃ analogue, 1α, 25-dihydroxy-23-oxavitamin D₃, 1α, 25-dihydroxy-23-thiavitamin D₃, 1α, 25-dihydroxy-23-azavitamin D₃, differentiation-inducing activity, 1α, 25-dihydroxyvitamin D₃, 1α, 25-dihydroxy-22-oxavitamin D₃, vitamin D₃ synthesis

JOURNAL FREE ACCESS

1991 Volume 39 Issue 12 Pages 3221-3224

DOI https://doi.org/10.1248/cpb.39.3221

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Abstract

Three vitamin D₃ analogues, 1α, 25-dihydroxy-23-oxavitamin D₃ (3), 1α, 25-dihydroxy-23-thiavitamin D₃ (4) and 1α, 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 1α, 25-dihydroxyvitamin D₃ (1).

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