Synthesis and testing of 2α-Modified 1α,25-Dihydroxyvitamin D3 analogues with a double side chain

Marked cell differentiation activity

Yoshitomo Suhara, Atsushi Kittaka, Seishi Kishimoto, Martin J. Calverley, Toshie Fujishima, Nozomi Saito, Takayuki Sugiura, Keizo Waku, Hiroaki Takayama

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

The 2α-methyl-, 2α-(3-hydroxypropyl)-, and 2α-(3-hydroxypropoxy)-derivatives of the 'double side chain' analogue of 1α,25-dihydroxyvitamin D3 were synthesized using Trost A-ring/CD-ring connective strategy. Regarding the requisite A-ring building blocks, a new, high yield and stereoselective route to the 2α-methyl compound starting from D-glucose was developed. All three new analogues showed potent HL-60 cancer cell differentiation activity.

Original languageEnglish
Pages (from-to)3255-3258
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume12
Issue number22
DOIs
Publication statusPublished - 2002 Nov 18
Externally publishedYes

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Calcitriol
Cells
Derivatives
Glucose
Testing

ASJC Scopus subject areas

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

Cite this

Synthesis and testing of 2α-Modified 1α,25-Dihydroxyvitamin D3 analogues with a double side chain : Marked cell differentiation activity. / Suhara, Yoshitomo; Kittaka, Atsushi; Kishimoto, Seishi; Calverley, Martin J.; Fujishima, Toshie; Saito, Nozomi; Sugiura, Takayuki; Waku, Keizo; Takayama, Hiroaki.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 12, No. 22, 18.11.2002, p. 3255-3258.

Research output: Contribution to journalArticle

Suhara, Yoshitomo ; Kittaka, Atsushi ; Kishimoto, Seishi ; Calverley, Martin J. ; Fujishima, Toshie ; Saito, Nozomi ; Sugiura, Takayuki ; Waku, Keizo ; Takayama, Hiroaki. / Synthesis and testing of 2α-Modified 1α,25-Dihydroxyvitamin D3 analogues with a double side chain : Marked cell differentiation activity. In: Bioorganic and Medicinal Chemistry Letters. 2002 ; Vol. 12, No. 22. pp. 3255-3258.
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