The synthesis and biological evaluation of 1-C-alkyl-l- arabinoiminofuranoses, a novel class of α-glucosidase inhibitors

Yoshihiro Natori; Tatsushi Imahori; Keiichi Murakami; Yuichi Yoshimura; Shinpei Nakagawa; Atsushi Kato; Isao Adachi; Hiroki Takahata

doi:10.1016/j.bmcl.2010.11.112

The synthesis and biological evaluation of 1-C-alkyl-l- arabinoiminofuranoses, a novel class of α-glucosidase inhibitors

Yoshihiro Natori, Tatsushi Imahori, Keiichi Murakami, Yuichi Yoshimura, Shinpei Nakagawa, Atsushi Kato, Isao Adachi, Hiroki Takahata^*

^*この論文の責任著者

薬剤部

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

41 被引用数 (Scopus)

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The asymmetric synthesis of 1-C-alkyl-l-arabinoiminofuranoses 1 was achieved by asymmetric allylic alkylation (AAA), ring closing metathesis (RCM), and Negishi cross coupling as key reactions. Some of the prepared compounds showed potent inhibitory activities towards intestinal maltase, with IC ₅₀ values comparable to those of commercial drugs such as acarbose, voglibose, and miglitol, which are used in the treatment of type 2 diabetes. Among them, the inhibitory activity (IC ₅₀ = 0.032 μM) towards intestinal sucrase of 1c was quite strong compared to the above commercial drugs.

本文言語	英語
ページ（範囲）	738-741
ページ数	4
ジャーナル	Bioorganic and Medicinal Chemistry Letters
巻	21
号	2
DOI	https://doi.org/10.1016/j.bmcl.2010.11.112
出版ステータス	出版済み - 2011/01/15

ASJC Scopus 主題領域

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

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10.1016/j.bmcl.2010.11.112

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title = "The synthesis and biological evaluation of 1-C-alkyl-l- arabinoiminofuranoses, a novel class of α-glucosidase inhibitors",

abstract = "The asymmetric synthesis of 1-C-alkyl-l-arabinoiminofuranoses 1 was achieved by asymmetric allylic alkylation (AAA), ring closing metathesis (RCM), and Negishi cross coupling as key reactions. Some of the prepared compounds showed potent inhibitory activities towards intestinal maltase, with IC 50 values comparable to those of commercial drugs such as acarbose, voglibose, and miglitol, which are used in the treatment of type 2 diabetes. Among them, the inhibitory activity (IC 50 = 0.032 μM) towards intestinal sucrase of 1c was quite strong compared to the above commercial drugs.",

keywords = "1-C-Alkyl-l-arabinoiminofuranose, Asymmetric allylic alkylation, Negishi cross coupling, Type 2 diabetes, α-Glucosidase inhibitor",

author = "Yoshihiro Natori and Tatsushi Imahori and Keiichi Murakami and Yuichi Yoshimura and Shinpei Nakagawa and Atsushi Kato and Isao Adachi and Hiroki Takahata",

note = "Funding Information: This study was financially supported by a Grant-in-Aid for Scientific Research from the Japan Society for the Promotion of Science (JSPS) . ",

year = "2011",

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doi = "10.1016/j.bmcl.2010.11.112",

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T1 - The synthesis and biological evaluation of 1-C-alkyl-l- arabinoiminofuranoses, a novel class of α-glucosidase inhibitors

AU - Natori, Yoshihiro

AU - Imahori, Tatsushi

AU - Murakami, Keiichi

AU - Yoshimura, Yuichi

AU - Nakagawa, Shinpei

AU - Kato, Atsushi

AU - Adachi, Isao

AU - Takahata, Hiroki

N1 - Funding Information: This study was financially supported by a Grant-in-Aid for Scientific Research from the Japan Society for the Promotion of Science (JSPS) .

PY - 2011/1/15

Y1 - 2011/1/15

N2 - The asymmetric synthesis of 1-C-alkyl-l-arabinoiminofuranoses 1 was achieved by asymmetric allylic alkylation (AAA), ring closing metathesis (RCM), and Negishi cross coupling as key reactions. Some of the prepared compounds showed potent inhibitory activities towards intestinal maltase, with IC 50 values comparable to those of commercial drugs such as acarbose, voglibose, and miglitol, which are used in the treatment of type 2 diabetes. Among them, the inhibitory activity (IC 50 = 0.032 μM) towards intestinal sucrase of 1c was quite strong compared to the above commercial drugs.

AB - The asymmetric synthesis of 1-C-alkyl-l-arabinoiminofuranoses 1 was achieved by asymmetric allylic alkylation (AAA), ring closing metathesis (RCM), and Negishi cross coupling as key reactions. Some of the prepared compounds showed potent inhibitory activities towards intestinal maltase, with IC 50 values comparable to those of commercial drugs such as acarbose, voglibose, and miglitol, which are used in the treatment of type 2 diabetes. Among them, the inhibitory activity (IC 50 = 0.032 μM) towards intestinal sucrase of 1c was quite strong compared to the above commercial drugs.

KW - 1-C-Alkyl-l-arabinoiminofuranose

KW - Asymmetric allylic alkylation

KW - Negishi cross coupling

KW - Type 2 diabetes

KW - α-Glucosidase inhibitor

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U2 - 10.1016/j.bmcl.2010.11.112

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SN - 0960-894X

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SP - 738

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JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

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The synthesis and biological evaluation of 1-C-alkyl-l- arabinoiminofuranoses, a novel class of α-glucosidase inhibitors

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