Synthesis and AMPA receptor antagonistic activity of a novel 7-imidazolyl-6-trifluoromethyl quinoxalinecarboxylic acid with a substituted phenyl group and improved its good physicochemical properties by introduced CF3 group

Bioorganic & Medicinal Chemistry Letters
Yasuo TakanoTakashi Uno

Abstract

We describe the synthesis, physicochemical, and biological properties of a novel series of 7-imidazolyl-6-trifluoromethyl quinoxalinecarboxylic acids with a substituted phenyl group attached through a urethane linkage at the C-7 position. We found that the introduction of trifluoromethyl group at the C-6 position brought about good biological activity and physicochemical properties. Among them, compound 9k (KRP-199), which has a 4-carboxyphenyl group, was found to possess high potency and selectivity for the AMPA-R in vitro and to exhibit good neuroprotective effects in vivo. Furthermore, the compound showed good physicochemical properties such as stability to light and good solubility in aqueous solutions.

References

Jan 1, 1981·Journal of Cerebral Blood Flow and Metabolism : Official Journal of the International Society of Cerebral Blood Flow and Metabolism·A TamuraG M Teasdale

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Citations

Aug 8, 2006·Medicinal Research Reviews·Daniela CatarziFlavia Varano
Apr 21, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Muhammad TahaZainul Amiruddin Zakaria

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