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^*

^*Corresponding author for this work

Hospital Pharmacy

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

41 Scopus citations

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.

Original language	English
Pages (from-to)	738-741
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	21
Issue number	2
DOIs	https://doi.org/10.1016/j.bmcl.2010.11.112
State	Published - 2011/01/15

Keywords

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

ASJC Scopus subject areas

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

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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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day = "15",

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

language = "英語",

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pages = "738--741",

journal = "Bioorganic and Medicinal Chemistry Letters",

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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

DO - 10.1016/j.bmcl.2010.11.112

M3 - 学術論文

C2 - 21185187

AN - SCOPUS:78651247063

SN - 0960-894X

VL - 21

SP - 738

EP - 741

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 2

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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