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Synthetic studies of vitamin D analogues. XVII. Synthesis and differentiation-inducing activity of 1 alpha,24-dihydroxy-22-oxavitamin D3 analogues and their 20 (R) -epimers

Kubodera, N.; Watanabe, H.; Miyamoto, K.; Matsumoto, M.; Matsuoka, S.; Kawanishi, T.

Chemical and Pharmaceutical Bulletin 41(9): 1659-1663

1993

ISSN/ISBN: 0009-2363
PMID: 8221979
DOI: 10.1248/cpb.41.1659
Accession: 047517907
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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).

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