A concise and efficient route to 2α-(ω-hydroxyalkoxy)-1α,25-dihydroxyvitamin D3: Remarkably high affinity to vitamin D receptor

Atsushi Kittaka, Yoshitomo Suhara, Hitoshi Takayanagi, Toshie Fujishima, Masaaki Kurihara, Hiroaki Takayama

Research output: Contribution to journalArticle

78 Citations (Scopus)

Abstract

(equation presented) A convenient and potentially valuable synthetic approach to the novel 2α-functionalized 1α,25-dihydroxyvitamin D3 [1α,25(OH)2D3] derivatives (1a-c), which are the C2-epimer of ED-71 and its analogues, has been developed. The C2α-modified ring A precursors (1,7-enynes 16, n = 0, 1, and 2) were constructed stereoselectively starting from D-glucose in high yield. In the synthesized 2α-(ω-hydroxyalkoxy)-1α,25(OH)2D3 derivatives, 1a and 1b showed a greater binding affinity to vitamin D receptor (VDR), up to 1.8 times that of the native hormone.

Original languageEnglish
Pages (from-to)2619-2622
Number of pages4
JournalOrganic Letters
Volume2
Issue number17
Publication statusPublished - 2000 Aug 24
Externally publishedYes

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calciferol
Calcitriol Receptors
hormones
Calcitriol
glucose
affinity
routes
analogs
Derivatives
rings
Hormones
Glucose

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

A concise and efficient route to 2α-(ω-hydroxyalkoxy)-1α,25-dihydroxyvitamin D3 : Remarkably high affinity to vitamin D receptor. / Kittaka, Atsushi; Suhara, Yoshitomo; Takayanagi, Hitoshi; Fujishima, Toshie; Kurihara, Masaaki; Takayama, Hiroaki.

In: Organic Letters, Vol. 2, No. 17, 24.08.2000, p. 2619-2622.

Research output: Contribution to journalArticle

Kittaka, A, Suhara, Y, Takayanagi, H, Fujishima, T, Kurihara, M & Takayama, H 2000, 'A concise and efficient route to 2α-(ω-hydroxyalkoxy)-1α,25-dihydroxyvitamin D3: Remarkably high affinity to vitamin D receptor', Organic Letters, vol. 2, no. 17, pp. 2619-2622.
Kittaka, Atsushi ; Suhara, Yoshitomo ; Takayanagi, Hitoshi ; Fujishima, Toshie ; Kurihara, Masaaki ; Takayama, Hiroaki. / A concise and efficient route to 2α-(ω-hydroxyalkoxy)-1α,25-dihydroxyvitamin D3 : Remarkably high affinity to vitamin D receptor. In: Organic Letters. 2000 ; Vol. 2, No. 17. pp. 2619-2622.
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