Metabolites of felbamate; synthesis of 2-(4-hydroxyphenyl)-1,3-propanediol dicarbamate, 2-phenyl-2-hydroxy-1,3-propanediol dicarbamate,and 2-phenyl-1,3-propanediol monocarbamate |
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Affiliation: | 1. Department of Anatomy, Physiology, and Pharmacology (APP), 107 Wiggins Road, University of Saskatchewan, Saskatoon, S7N 5E5, SK, Canada;2. Deptament of Anatomy, Physiology, and Pharmacology (APP), University of Saskatchewan, & Cameco MS Neuroscience Research Centre, 701 Queen St., Saskatoon, S7K 0M7, SK, Canada;3. Department of Biochemistry and Molecular Vascular Biology, Kanazawa University Graduate School of Medical Science, Kanazawa, 920-8640, Japan |
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Abstract: | Three major metabolites of felbamate, namely 2-(4-hydroxyphyenyl)-1, 3-propanediol dicarbamate. [4], 2-hydroxy-2-phenyl-1,3-propanediol dicarbamat [12], and 2-phenyl-1,3-propanediol monocarbamate [17] were prepared. The first metabolite, 4, was synthesised from p-methoxy-phenylacetic acid [1] via five steps involving carboxylation, reduction, phosgenation, demethylation, and carbonation. The second one, 12, was prepared from 2-phenyl-1,3-propanediol [7] by the following five steps; phosgenation, halogenation, carbonation, dehalogenation, and ammonolysis. The synthesis of the third metabolite, 17, started with 7, via the following five steps: methylation, phosgenation, carbonation, and demethylation. |
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