Synthetic Studies of Vitamin D Analogues. XI. Synthesis and Differentiation-Inducing Activity of 1α, 25-Dihydroxy-22-oxavitamin D3 Analogues

Noboru KUBODERA; Hiroyoshi WATANABE; Takehiko KAWANISHI; Masahiko MATSUMOTO

doi:10.1248/cpb.40.1494

Synthetic Studies of Vitamin D Analogues. XI. Synthesis and Differentiation-Inducing Activity of 1α, 25-Dihydroxy-22-oxavitamin D₃ Analogues

Noboru KUBODERA, Hiroyoshi WATANABE, Takehiko KAWANISHI, Masahiko MATSUMOTO

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Keywords: 1α, 25-dihydroxyvitamin D₃, 1α, 25-dihydroxy-22-oxavitamin D₃, irradiation, thermal isomerization, differentiation-inducing activity, calcium phosphorous metabolism

JOURNAL FREE ACCESS

1992 Volume 40 Issue 6 Pages 1494-1499

DOI https://doi.org/10.1248/cpb.40.1494

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Abstract

Six analogues of 1α, 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 1α, 25-dihydroxyvitamin D₃ (1) receptor are also described.

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