Concise synthesis and biological activities of 2α-alkyl- and 2α-(ω-hydroxyalkyl)-20-epi-1α,25-dihydroxyvitamin D 3

Shinobu Honzawa, Yoshitomo Suhara, Ken Ichi Nihei, Nozomi Saito, Seishi Kishimoto, Toshie Fujishima, Masaaki Kurihara, Takayuki Sugiura, Keizo Waku, Hiroaki Takayama, Atsushi Kittaka

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

We found a concise route to the Trost A-ring precursor enyne for synthesizing 2α-alkylated 1α,25-dihydroxyvitamin D3 (1) from D-glucose. The enynes were coupled with the 20-epi-CD ring part to study the effect of the double modification of 2α-substitution and 20-epimerization upon biological activities of 1. The novel three analogues of 2α-alkyl- and four analogues of 2α-(ω -hydroxyalkyl)-20-epi-1α,25-dihydroxyvitamin D3 (5b-d and 6a-d) showed higher binding affinity for vitamin D receptor (VDR) and more potent activity in induction of HL-60 cell differentiation than those of the natural hormone 1.

Original languageEnglish
Pages (from-to)3503-3506
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume13
Issue number20
DOIs
Publication statusPublished - 2003 Oct 20
Externally publishedYes

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Calcitriol
Bioactivity
Calcitriol Receptors
Substitution reactions
Hormones
Glucose
1,25-dihydroxyvitamin D

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

Concise synthesis and biological activities of 2α-alkyl- and 2α-(ω-hydroxyalkyl)-20-epi-1α,25-dihydroxyvitamin D 3. / Honzawa, Shinobu; Suhara, Yoshitomo; Nihei, Ken Ichi; Saito, Nozomi; Kishimoto, Seishi; Fujishima, Toshie; Kurihara, Masaaki; Sugiura, Takayuki; Waku, Keizo; Takayama, Hiroaki; Kittaka, Atsushi.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 13, No. 20, 20.10.2003, p. 3503-3506.

Research output: Contribution to journalArticle

Honzawa, S, Suhara, Y, Nihei, KI, Saito, N, Kishimoto, S, Fujishima, T, Kurihara, M, Sugiura, T, Waku, K, Takayama, H & Kittaka, A 2003, 'Concise synthesis and biological activities of 2α-alkyl- and 2α-(ω-hydroxyalkyl)-20-epi-1α,25-dihydroxyvitamin D 3', Bioorganic and Medicinal Chemistry Letters, vol. 13, no. 20, pp. 3503-3506. https://doi.org/10.1016/S0960-894X(03)00739-X
Honzawa, Shinobu ; Suhara, Yoshitomo ; Nihei, Ken Ichi ; Saito, Nozomi ; Kishimoto, Seishi ; Fujishima, Toshie ; Kurihara, Masaaki ; Sugiura, Takayuki ; Waku, Keizo ; Takayama, Hiroaki ; Kittaka, Atsushi. / Concise synthesis and biological activities of 2α-alkyl- and 2α-(ω-hydroxyalkyl)-20-epi-1α,25-dihydroxyvitamin D 3. In: Bioorganic and Medicinal Chemistry Letters. 2003 ; Vol. 13, No. 20. pp. 3503-3506.
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AU - Saito, Nozomi

AU - Kishimoto, Seishi

AU - Fujishima, Toshie

AU - Kurihara, Masaaki

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AU - Waku, Keizo

AU - Takayama, Hiroaki

AU - Kittaka, Atsushi

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