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

16 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

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ASJC Scopus subject areas

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

Cite this

Suhara, Y., Kittaka, A., Ono, K., Kurihara, M., Fujishima, T., Yoshida, A., & Takayama, H. (2002). Design and efficient synthesis of new stable 1α,25-dihydroxy-19-norvitamin D₃ analogues containing amide bond. Bioorganic and Medicinal Chemistry Letters, 12(24), 3533-3536. https://doi.org/10.1016/S0960-894X(02)00800-4

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

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