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

研究成果: Article › 査読

18 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	3533-3536
ページ数	4
ジャーナル	Bioorganic and Medicinal Chemistry Letters
巻	12
号	24
DOI	https://doi.org/10.1016/S0960-894X(02)00800-4
出版ステータス	Published - 2002 12月
外部発表	はい

ASJC Scopus subject areas

生化学
分子医療
分子生物学
薬科学
創薬
臨床生化学
有機化学

文献へのアクセス

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

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引用スタイル

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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.",

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AU - Kittaka, Atsushi

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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.

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