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

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• 作者：Yoshihiro Natori^a ; Tatsushi Imahori^a ; Keiichi Murakami^a ; Yuichi Yoshimura^a ; Shinpei Nakagawa^b ; Atsushi Kato^b ; Isao Adachi^b ; Hiroki Takahata^a ; ^{takahata@tohoku-pharm.ac.jp}
• 关键词：1-C-Alkyl-l-arabinoiminofuranose ; α ; -Glucosidase inhibitor ; Asymmetric allylic alkylation ; Negishi cross coupling ; Type 2 diabetes
• 刊名：Bioorganic and Medicinal Chemistry Letters
• 出版年：2011
• 出版时间：15 January 2011
• 年：2011
• 卷：21
• 期：2
• 页码：738-741
• 全文大小：310 K

文摘

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 IC₅₀ 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 (IC₅₀ = 0.032 μM) towards intestinal sucrase of 1c was quite strong compared to the above commercial drugs.