P-26 C1位アルキルL-アラビノイミノフラノース誘導体の触媒的不斉合成とその生物活性評価(ポスター発表の部)
書誌事項
- タイトル別名
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- P-26 Catalytic Enantioselective Synthesis and Biological Evaluation of 1-C-Alkyl-L-arabinoiminofuranose derivatives(Poster Presentation)
抄録
Iminosugars have emerged as potent inhibitors of glucosidases and glucosyltransferases, due to their transition state analogues in the enzymatic reactions. Therefore, many enantioselective syntheses of iminosugars have been reported in recent years. However, up to now, much attention has been focused on the synthesis of their D-forms. There were few reports of systematic studies of the biological properties of the L-forms of iminosugars. Herein, we report both catalytic enantioselective synthesis and biological evaluation of 1-C-alkyl-L-arabinoiminofuranose derivatives 2. We prepared iodoalkane 8 as the key intermediate for the synthesis of desired iminofuranose derivatives via asymmetric allylic aminations and ring-closing metathesis. Ni-catalyzed Negishi cross-coupling of 8 with many alkyl zinc halides proceed to give the desired products 9 in moderate yields. With 9 in hand, we have converted from coupling products into various 1-C-alkyl L-arabino-iminofuranose derivatives 2 in 3 steps (Scheme 2). Some of the synthesized iminofuranoses were found to be potent inhibitors of a-glucosidases, and their inhibitions were comparable to those of commercially available drugs such as acarbose, voglibose, and miglitol for the treatment of type 2 diabetes. Especially, 1-C-butyl-L-arabinoiminofuranose 2c showed much powerful inhibitory activity for rat intestinal sucrase. Additionally, we prepared iminosugar 12 having 1-hydroxybutyl group as 1-C-alkyl units and their inhibitory activities toward a-glucosidase were measured.
収録刊行物
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- 天然有機化合物討論会講演要旨集
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天然有機化合物討論会講演要旨集 53 (0), 559-564, 2011
天然有機化合物討論会実行委員会
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詳細情報 詳細情報について
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- CRID
- 1390282681056742528
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- NII論文ID
- 110009986595
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- ISSN
- 24331856
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- 本文言語コード
- ja
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- データソース種別
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- JaLC
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可
