4.5 Article

Synthesis of L-(+)-3-(3-hydroxy-4-pivaloyloxybenzyl)-2,5-diketomorpholine as potential prodrug of L-dopa

Journal

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 10, Issue 12, Pages 1385-1388

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PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0960-894X(00)00249-3

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The synthesis and in vitro chemical and enzymatic stability of L-(+)-3-(3-hydroxy-4-pivaloyloxybenzyl)-2-5-diketomorpholine (9) as L-Dopa prodrug are described. Prodrug 9 possesses a good lipophilicity (log P = 2.153 +/- 0.017), is stable in aqueous buffer solutions (pH 1.3 and 7.4), and in 80% rat and human plasma it is turned into L-Dopa. (C) 2000 Elsevier Science Ltd. All rights reserved.

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