Synthetic Studies of Vitamin D Analogues. XVII.Synthesis and Differentiation-Inducing Activity of 1α, 24-Dihydroxy-22-oxavitamin D3 Analogues and Their 20(R)-Epimers

1 January 1993

journal article
Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN

Vol. 41 (9) , 1659-1663
https://doi.org/10.1248/cpb.41.1659

Abstract

Four vitamin D3 analogues, 1 alpha,24(S)- and 1 alpha,24(R)-dihydroxy-22-oxavitamin D3 (5 and 6) and their 20(R)-epimers (7 and 8) were synthesized from the 20(S)-alcohol (10). In tests of activity to induce differentiation of human myeloid leukemia cells (HL-60) to macrophages, 5 showed comparable activity to 1 alpha,25-dihydroxy-22-oxavitamin D3 (OCT) (2), and the other three analogues (6, 7 and 8) were less active than OCT (2). The binding properties of these analogues to the chick embryonic intestinal 1 alpha,25-dihydroxyvitamin D3 (1) receptor were evaluated. Furthermore, 20(R)-OCT (9) was synthesized and its biological properties were compared with those of OCT(2) and the 20(R)-epimers (7 and 8).

Keywords

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