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Highly potent cell differentiation-inducing analogues of 1α,25-dihydroxyvitamin D3: synthesis and biological activity of 2-methyl-1,25-dihydroxyvitamin D3 with side-chain modifications by Toshie Fujishima; Liu Zhaopeng; Katsuhiro Konno; Kimie Nakagawa; Toshio Okano; Kentaro Yamaguchi; Hiroaki Takayama is a Biochemistry, Genetics and Molecular Biology article available to read on EtoBox.

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AbstractÐEight 2-methyl substituted analogues of 20-epi-22R-methyl-1a,25-dihydroxyvitamin D 3 (5) and 20-epi-24,26,27-trihomo-22-oxa-1a,25-dihydroxyvitamin D 3 (6: KH-1060) were convergently synthesized. Preparation of the CD-ring portions with modi®ed side chains of 5 and 6, followed by palladium-catalyzed cross-coupling with the A-ring enyne synthons (20a±d), (3S,4S,5R)-, (3S,4R,5R)-, (3S,4S,5S)-and (3R,4R,5S)-3,5-bis[(tert-butyldimethylsilyl)oxy]-4-methyloct-1-en-7-yne, aorded two sets of four A-ring stereoisomers of 20-epi-2,22-dimethyl-1,25-dihydroxyvitamin D 3 (7a±d) and 20-epi-24,26,27-trihomo-2-methyl-22-oxa-1,25dihydroxyvitamin D 3 (8a±d). The biological pro®les of the hybrid analogues were assessed in terms of anity for vitamin D receptor (VDR) and HL-60 cell dierentiation-inducing activity in comparison with the natural hormone. The combined modi®cations of the A-ring at the 2-position and the side chain yielded analogues with high potency.

Who reads Highly potent cell differentiation-inducing analogues of 1α,25-dihydroxyvitamin D3: synthesis and biological activity of 2-methyl-1,25-dihydroxyvitamin D3 with side-chain modifications?

Author

Toshie Fujishima; Liu Zhaopeng; Katsuhiro Konno; Kimie Nakagawa; Toshio Okano; Kentaro Yamaguchi; Hiroaki Takayama

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0968-0896)

Published

2001

Language

EN

Field

Biochemistry, Genetics and Molecular Biology (Life Sciences)