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Synthetic studies of vitamin D analogues. XI. Synthesis and differentiation-inducing activity of 1 alpha,25-dihydroxy-22-oxavitamin D3 analogues

Kubodera, N.; Watanabe, H.; Kawanishi, T.; Matsumoto, M.

Chemical and Pharmaceutical Bulletin 40(6): 1494-1499

1992

ISSN/ISBN: 0009-2363
PMID: 1327561
DOI: 10.1248/cpb.40.1494
Accession: 041524555
Six analogues of 1 alpha,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 1 alpha,25-dihydroxyvitamin D3 (1) receptor are also described.

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Related References

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