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Synthesis of Thieno[2,3-d]oxazines and Thieno[2,3-d]thiazines as Subtype Specific Kainate Receptor Antagonists

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For the development of new antiepileptics the kainate receptors, GluR6 and GluR5, are important targets. Based on the anticonvulsant effects of chinazolines and thieno[2,3-d]pyrimidines that are known from the literature, thieno[2,3-d][1.3]oxazines were synthesized and studied for their inhibitory properties at GluR6 and GluR5 receptors. The strongest inhibitor activity was observed with 5-methyl-6-phenyl-thieno[2,3-d][1.3]oxazines with C1 or C3-substituents in position 2 (3b-f). The 2-trihalide-methyl-substituted compounds 3c and 3d were the most active inhibitors at the GluR5- receptor (IC50=23.4 μmol, 16 μl). The 2-isopropyl-substituted compound 3f displayed the strongest activity at the GluR6- receptor (IC50=8.7 μmol). A number of thieno[2,3-d][1.3]thiazines and thieno[2,3-d]pyrimidines that were synthesized from the thieno[2,3][1.3]oxazines did not show any activity.

Keywords: Glutamate receptor antagonists; anticonvulsives; kainate receptor antagonists; thieno[2,3-d]-pyrimidines; thieno[2,3-d][1.3]oxazines; thieno[2,3-d][1.3]thiazines

Document Type: Research Article


Affiliations: Institute of Pharmacy, Faculty of Biosciences, Pharmacy and Psychology, University of Leipzig, Bruderstra├če 34, 04103 Leipzig, Germany.

Publication date: December 1, 2009

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