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• W2027503277 abstract "(RS)-2-Amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionic acid (AMPA, 5) and the selective AMPA receptor antagonist (RS)-2-amino-3-[3-(carboxymethoxy)-5-methyl-4-isoxazolyl]propionic acid (AMOA, 7) have been used as leads for the design and synthesis of a number of potential AMPA receptor antagonists. Two parallel series of AMOA analogs were synthesized, containing either a distal carboxylic acid (compounds 8b−g and 11b) or a phosphonic acid (compounds 9a−g, 10c, and 11c). Pharmacological characterization of the synthesized compounds was carried out using a series of receptor binding assays and by in vitro electrophysiological experiments using the rat cortical slice model. The two analogs with a tert-butyl substituent, (RS)-2-amino-3-[5-tert-butyl-3-(carboxymethoxy)-4-isoxazolyl]propionic acid (ATOA, 8b) and the corresponding phosphonic acid analog ATPO (9b), were the most potent and selective AMPA antagonists within each series. ATOA and ATPO showed IC50 values of 150 and 28 μM, respectively, toward AMPA-induced depolarizations in the cortical slice model compared to IC50 = 320 μM for the parent compound, AMOA. These two new competitive AMPA antagonists were significantly more selective than AMOA, showing no antagonism (up to 1 mM) toward NMDA-induced responses, whereas AMOA (at 1 mM) showed weak (19%) inhibition toward NMDA-induced responses. The structure−activity relationships for the two series of compounds revealed considerable differences with respect to the substituents effects, and the phosphonic acid analogs generally exhibited significantly higher potencies compared to the carboxylic acid analogs." @default.
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• W2027503277 date "1996-01-01" @default.
• W2027503277 modified "2023-10-06" @default.
• W2027503277 title "Synthesis and Pharmacology of Highly Selective Carboxy and Phosphono Isoxazole Amino Acid AMPA Receptor Antagonists" @default.
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• W2027503277 doi "https://doi.org/10.1021/jm950826p" @default.
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