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.
authors: Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, Sendai 981-8558, Japan.
authors: Yoshihiro
authors: Y
authors: Natori
authors: Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, Sendai 981-8558, Japan.
authors: Toshihiro
authors: T
authors: Sakuma
authors: Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, Sendai 981-8558, Japan. Electronic address: yoshimura@tohoku-pharm.ac.jp.
authors: Yuichi
authors: Y
authors: Yoshimura
authors: Department of Hospital Pharmacy, University of Toyama, Toyama 930-0194, Japan.
authors: Kyoko
authors: K
authors: Kinami
authors: Department of Hospital Pharmacy, University of Toyama, Toyama 930-0194, Japan.
authors: Yuki
authors: Y
authors: Hirokami
authors: Department of Hospital Pharmacy, University of Toyama, Toyama 930-0194, Japan.
authors: Kasumi
authors: K
authors: Sato
authors: Department of Hospital Pharmacy, University of Toyama, Toyama 930-0194, Japan.
authors: Isao
authors: I
authors: Adachi
authors: Department of Hospital Pharmacy, University of Toyama, Toyama 930-0194, Japan. Electronic address: kato@med.u-toyama.ac.jp.
authors: Atsushi
authors: A
authors: Kato
authors: Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, Sendai 981-8558, Japan.
authors: Hiroki
authors: H
authors: Takahata
mesh_terms: D004305:Dose-Response Relationship, Drug; D065089:Glycoside Hydrolase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D050111:Imino Sugars / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D007422:Intestines / Q000201:enzymology; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D000520:alpha-Glucosidases / Q000378:metabolism*
chemical_list: C000595738:1-(4-(3,5-difluorophenyl)butyl)iminofuranose; D065089:Glycoside Hydrolase Inhibitors; D050111:Imino Sugars; D000520:alpha-Glucosidases
keywords: 1-C-4′-Arylbutyl-l-arabinoiminofuranoses; Iminosugars; Structure–activity relationship; Type-2 diabetes; α-Glucosidase inhibitor