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

doi:10.1016/S0960-894X(02)00800-4

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 journal › Article › peer-review

17 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 language	English
Pages (from-to)	3533-3536
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	12
Issue number	24
DOIs	https://doi.org/10.1016/S0960-894X(02)00800-4
Publication status	Published - 2002 Dec 1
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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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, 01.12.2002, p. 3533-3536.

Research output: Contribution to journal › Article › peer-review

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