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

18 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
Externally published	Yes

ASJC Scopus subject areas

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

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

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

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.",

author = "Yoshitomo Suhara and Atsushi Kittaka and Keiichiro Ono and Masaaki Kurihara and Toshie Fujishima and Akihiro Yoshida and Hiroaki Takayama",

note = "Funding Information: We are grateful to Miss Junko Shimode and Miss Maroka Kitsukawa for the spectroscopic measurements. This work was supported in part by Kanagawa Academy of Science and Technology Research Grants, which we gratefully acknowledge. Copyright: Copyright 2008 Elsevier B.V., All rights reserved.",

year = "2002",

month = dec,

doi = "10.1016/S0960-894X(02)00800-4",

language = "English",

volume = "12",

pages = "3533--3536",

journal = "Bioorganic and Medicinal Chemistry Letters",

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TY - JOUR

T1 - Design and efficient synthesis of new stable 1α,25-dihydroxy-19-norvitamin D3 analogues containing amide bond

AU - Suhara, Yoshitomo

AU - Kittaka, Atsushi

AU - Ono, Keiichiro

AU - Kurihara, Masaaki

AU - Fujishima, Toshie

AU - Yoshida, Akihiro

AU - Takayama, Hiroaki

N1 - Funding Information: We are grateful to Miss Junko Shimode and Miss Maroka Kitsukawa for the spectroscopic measurements. This work was supported in part by Kanagawa Academy of Science and Technology Research Grants, which we gratefully acknowledge. Copyright: Copyright 2008 Elsevier B.V., All rights reserved.

PY - 2002/12

Y1 - 2002/12

N2 - 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.

AB - 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.

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JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

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ER -

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

Abstract

ASJC Scopus subject areas

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