Synthesis and anticonvulsant activities of (R)-(O)-methylserine derivatives |
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| Affiliation: | 1. Department of Chemistry, University of Houston, Houston, TX 77204-5641, USA;2. Epilepsy Branch, National Institute of Neurological Disorders and Stroke, National Institutes of Health, Federal Building, Room 114, Bethesda, MD 20892-9020, USA;1. Department of Organic Chemistry, Faculty of Science, Institute of Molecular and Translational Medicine, University of Palacky, 771 46 Olomouc, Czech Republic;2. Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Center, Notre Dame, IN 46556, USA;1. Department of Civil Engineering, Collage of Engineering, Qassim University, P. O. Box 6677, Buraidah 51452, Saudi Arabia;2. Department of Civil Engineering, College of Engineering, King Saud University, P.O. Box 800, Riyadh 11421, Saudi Arabia;3. Department of Chemical and Environmental Engineering, Masdar Institute of Science and Technology, P.O. Box 54224, Abu Dhabi, United Arab Emirates;1. Inorganic Chemistry Department, National Taras Shevchenko University of Kyiv, Volodymyrska Street 64, Kyiv 01033, Ukraine;2. Institute of Organic Chemistry, Murmanska Str. 5, Kyiv 02660, Ukraine |
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| Abstract: | Efficient procedures for the synthesis of (R)-N-benzyl-2-amino-3-methoxypropionamide ((R)-3), 2-acetamido-3-methoxypropionic acid (4), and O-methylserine (5) are described beginning from (R)-Cbz-serine ((R)-7). The reactions proceeded with little or no racemization and permitted the synthesis of the potent anticonvulsant (R)-N-benzyl-2-acetamido-3-methoxypropionamide ((R)-2). The anticonvulsant activities of 2–4 were determined revealing the surprising activity of (R)-2. |
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