Design and efficient synthesis of new stable 1α,25-dihydroxy-19-norvitamin D3 analogues containing amide bond

Yoshitomo Suhara, Atsushi Kittaka, Keiichiro Ono, Masaaki Kurihara, Toshie Fujishima, Akihiro Yoshida, Hiroaki Takayama

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

The design and synthesis of new 1α,25-dihydroxy-19-norvitamin D3 analogues 3a-c, which have an amide bond in the molecule instead of the diene, are described. The A-ring moiety was constructed by a (3S,5S)-3,5-dihydroxypiperidine derivative (9, 11, or 13) prepared from D-mannose, and a CD-ring carboxylic acid 16 was synthesized from Grundmann's ketone. Coupling those parts gave desired 3a-c in good yield. This strategy can be applied in combinatorial chemistry; therefore, those compounds would be applicable as useful tools in the development of new drugs.

Original languageEnglish
Pages (from-to)3533-3536
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume12
Issue number24
DOIs
Publication statusPublished - 2002 Dec
Externally publishedYes

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Mannose
Carboxylic Acids
Ketones
Amides
Derivatives
Molecules
Pharmaceutical Preparations
1,25-dihydroxy-19-norvitamin D3

ASJC Scopus subject areas

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

Cite this

Design and efficient synthesis of new stable 1α,25-dihydroxy-19-norvitamin D3 analogues containing amide bond. / Suhara, Yoshitomo; Kittaka, Atsushi; Ono, Keiichiro; Kurihara, Masaaki; Fujishima, Toshie; Yoshida, Akihiro; Takayama, Hiroaki.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 12, No. 24, 12.2002, p. 3533-3536.

Research output: Contribution to journalArticle

Suhara, Yoshitomo ; Kittaka, Atsushi ; Ono, Keiichiro ; Kurihara, Masaaki ; Fujishima, Toshie ; Yoshida, Akihiro ; Takayama, Hiroaki. / Design and efficient synthesis of new stable 1α,25-dihydroxy-19-norvitamin D3 analogues containing amide bond. In: Bioorganic and Medicinal Chemistry Letters. 2002 ; Vol. 12, No. 24. pp. 3533-3536.
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