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Improved synthesis and in vitro/in vivo activities of natural product-inspired, artificial glutamate analogs

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タイトル: Improved synthesis and in vitro/in vivo activities of natural product-inspired, artificial glutamate analogs
著者: Oikawa, Masato 著作を一覧する
Ikoma, Minoru 著作を一覧する
Sasaki, Makoto 著作を一覧する
Gill, Martin B. 著作を一覧する
Swanson, Geoffrey T. 著作を一覧する
Shimamoto, Keiko 著作を一覧する
Sakai, Ryuichi 著作を一覧する
キーワード: Diversity-oriented synthesis
Glutamate receptor
Hypoactivity
Deoxygenation of amide
発行日: 2010年 6月 1日
出版者: Elsevier
誌名: Bioorganic & Medicinal Chemistry
巻: 18
号: 11
開始ページ: 3795
終了ページ: 3804
出版社 DOI: 10.1016/j.bmc.2010.04.044
抄録: Here, we report our second-generation synthesis of 12 artificial glutamate analogs, starting from heterotricycle intermediates 3a-3d, readily prepared in three steps including tandem Ugi/Diels-Alder reactions. The new synthesis employs imidate intermediates for the deoxygenation of pyrrolidones (10a-10d to 6a-6d), and each advanced intermediate 6a-6d was diversified into three glutamate analogs (1a-1d, 5a-5d, 7a-7d) in 1-2 steps. In vitro electrophysiological assays revealed that the new piperidine-type analog 7c alters neuronal function with lower potency than 1a. Conversely, intracranial injection of 7c into mice produced a greater degree of hypoactivity than 1a. Our recent investigation has revealed that this series of compounds antagonizes AMPA-type glutamate receptor-mediated currents in a subtype selective manner. The more efficient syntheses of this novel set of neuroactive molecules will facilitate their pharmacological characterization.
資料タイプ: article (author version)
URI: http://hdl.handle.net/2115/43115
出現コレクション:雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

提供者: 酒井 隆一

 

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