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

Authors
Cingolani, GM Di Stefano, A Mosciatti, B Napolitani, F Giorgioni, G Ricciutelli, M Claudi, F
Citation
Gm. Cingolani et al., Synthesis of L-(+)-3-(3-hydroxy-4-pivaloyloxybenzyl)-2,5-diketomorpholine as potential prodrug of L-dopa, BIOORG MED, 10(12), 2000, pp. 1385-1388
Citations number
11
Categorie Soggetti
Chemistry & Analysis
Journal title
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
ISSN journal
0960894X → ACNP
Volume
10
Issue
12
Year of publication
2000
Pages
1385 - 1388
Database
ISI
SICI code
0960-894X(20000619)10:12<1385:SOLA>2.0.ZU;2-4
Abstract
The synthesis and in vitro chemical and enzymatic stability of L-(+)-3-(3-h ydroxy-4-pivaloyloxybenzyl)-2-5-diketomorpholine (9) as L-Dopa prodrug are described. Prodrug 9 possesses a good lipophilicity (log P = 2.153 +/- 0.01 7), 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. A ll rights reserved.