ArticleBioorganic & medicinal chemistry2010
Improved synthesis and in vitro/in vivo activities of natural product-inspired, artificial glutamate analogs.
Article in Bioorganic & medicinal chemistry, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Oxa-Michael-based divergent synthesis of artificial glutamate analogs.RSC advances · 2022Article
- Menthyl esterification allows chiral resolution for the synthesis of artificial glutamate analogs.Beilstein journal of organic chemistry · 2021Article
- Recent progress in neuroactive marine natural products.Natural product reports · 2014Review
- Studies on an (S)-2-amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionic acid (AMPA) receptor antagonist IKM-159: asymmetric synthesis, neuroactivity, and structural characterization.Journal of medicinal chemistry · 2013Article
- A series of structurally novel heterotricyclic alpha-amino-3-hydroxyl-5-methyl-4-isoxazole-propionate receptor-selective antagonists.British journal of pharmacology · 2010Article
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Authors and funding
7 authors.
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Abstract
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.
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