Synthesis and biological evaluation of α-1-C-4′-arylbutyl-l- arabinoiminofuranoses, a new class of α-glucosidase inhibitors

Yoshihiro Natori; Toshihiro Sakuma; Yuichi Yoshimura; Kyoko Kinami; Yuki Hirokami; Kasumi Sato; Isao Adachi; Atsushi Kato; Hiroki Takahata

doi:10.1016/j.bmcl.2014.06.001

Synthesis and biological evaluation of α-1-C-4′-arylbutyl-l- arabinoiminofuranoses, a new class of α-glucosidase inhibitors

Yoshihiro Natori, Toshihiro Sakuma, Yuichi Yoshimura^*, Kyoko Kinami, Yuki Hirokami, Kasumi Sato, Isao Adachi, Atsushi Kato, Hiroki Takahata

^*Corresponding author for this work

Hospital Pharmacy

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

9 Scopus citations

Abstract

A series of α-1-C-4′-arylbutyl-l-arabinoiminofuranoses 3 with functional groups attached to the phenyl ring, which are potential α-glycosidase inhibitors, was designed and synthesized by using a Negishi cross-coupling reaction as the key reaction. Arylbutyl derivatives 3a-e showed potent inhibitory activities against intestinal maltase. Among them, difluorophenylbutyl derivative 3e showed good inhibition activities against intestinal isomaltase and sucrase as compared to those of 1 and commercial drugs.

Original language	English
Pages (from-to)	3298-3301
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	24
Issue number	15
DOIs	https://doi.org/10.1016/j.bmcl.2014.06.001
State	Published - 2014/08/01

Keywords

1-C-4′-Arylbutyl-l-arabinoiminofuranoses
Iminosugars
Structure-activity relationship
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.2014.06.001

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title = "Synthesis and biological evaluation of α-1-C-4′-arylbutyl-l- arabinoiminofuranoses, a new class of α-glucosidase inhibitors",

abstract = "A series of α-1-C-4′-arylbutyl-l-arabinoiminofuranoses 3 with functional groups attached to the phenyl ring, which are potential α-glycosidase inhibitors, was designed and synthesized by using a Negishi cross-coupling reaction as the key reaction. Arylbutyl derivatives 3a-e showed potent inhibitory activities against intestinal maltase. Among them, difluorophenylbutyl derivative 3e showed good inhibition activities against intestinal isomaltase and sucrase as compared to those of 1 and commercial drugs.",

keywords = "1-C-4′-Arylbutyl-l-arabinoiminofuranoses, Iminosugars, Structure-activity relationship, Type-2 diabetes, α-Glucosidase inhibitor",

author = "Yoshihiro Natori and Toshihiro Sakuma and Yuichi Yoshimura and Kyoko Kinami and Yuki Hirokami and Kasumi Sato and Isao Adachi and Atsushi Kato and Hiroki Takahata",

note = "Funding Information: This work was supported in part by a Grant-in-Aid for Young Scientists (B) (No. 23790138 ) (Y.N.) from JSPS and by a Grant of Strategic Research Foundation Grant-aided Project for Private Universities from Ministry of Education, Culture, Sport, Science, and Technology, Japan ( MEXT ), 2010–2014. ",

year = "2014",

month = aug,

day = "1",

doi = "10.1016/j.bmcl.2014.06.001",

language = "英語",

volume = "24",

pages = "3298--3301",

journal = "Bioorganic and Medicinal Chemistry Letters",

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TY - JOUR

T1 - Synthesis and biological evaluation of α-1-C-4′-arylbutyl-l- arabinoiminofuranoses, a new class of α-glucosidase inhibitors

AU - Natori, Yoshihiro

AU - Sakuma, Toshihiro

AU - Yoshimura, Yuichi

AU - Kinami, Kyoko

AU - Hirokami, Yuki

AU - Sato, Kasumi

AU - Adachi, Isao

AU - Kato, Atsushi

AU - Takahata, Hiroki

N1 - Funding Information: This work was supported in part by a Grant-in-Aid for Young Scientists (B) (No. 23790138 ) (Y.N.) from JSPS and by a Grant of Strategic Research Foundation Grant-aided Project for Private Universities from Ministry of Education, Culture, Sport, Science, and Technology, Japan ( MEXT ), 2010–2014.

PY - 2014/8/1

Y1 - 2014/8/1

N2 - A series of α-1-C-4′-arylbutyl-l-arabinoiminofuranoses 3 with functional groups attached to the phenyl ring, which are potential α-glycosidase inhibitors, was designed and synthesized by using a Negishi cross-coupling reaction as the key reaction. Arylbutyl derivatives 3a-e showed potent inhibitory activities against intestinal maltase. Among them, difluorophenylbutyl derivative 3e showed good inhibition activities against intestinal isomaltase and sucrase as compared to those of 1 and commercial drugs.

AB - A series of α-1-C-4′-arylbutyl-l-arabinoiminofuranoses 3 with functional groups attached to the phenyl ring, which are potential α-glycosidase inhibitors, was designed and synthesized by using a Negishi cross-coupling reaction as the key reaction. Arylbutyl derivatives 3a-e showed potent inhibitory activities against intestinal maltase. Among them, difluorophenylbutyl derivative 3e showed good inhibition activities against intestinal isomaltase and sucrase as compared to those of 1 and commercial drugs.

KW - 1-C-4′-Arylbutyl-l-arabinoiminofuranoses

KW - Iminosugars

KW - Structure-activity relationship

KW - Type-2 diabetes

KW - α-Glucosidase inhibitor

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U2 - 10.1016/j.bmcl.2014.06.001

DO - 10.1016/j.bmcl.2014.06.001

M3 - 学術論文

C2 - 24973028

AN - SCOPUS:84904070409

SN - 0960-894X

VL - 24

SP - 3298

EP - 3301

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 15

ER -

Synthesis and biological evaluation of α-1-C-4′-arylbutyl-l- arabinoiminofuranoses, a new class of α-glucosidase inhibitors

Abstract

Keywords

ASJC Scopus subject areas

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