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Prodrugs nichtsteroidaler antirheumatika, 3. mitt.: Synthese und hydrolyse von acyloxy‐2‐oxopropanen
Author(s) -
Schwenker Gerhard,
Stiefvater Karlheinz
Publication year - 1991
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.2503240905
Subject(s) - chemistry , prodrug , hydrolysis , steric effects , chemical synthesis , stereochemistry , lability , chemical stability , lactone , medicinal chemistry , organic chemistry , in vitro , biochemistry
Synthesis and Hydrolysis of Acyloxy‐2‐oxopropanes 2‐Oxopropylesters are examined as potential prodrugs of acidic non‐steroidal anti‐inflammatory drugs. The esters are characterized by a high degree of chemical lability at pH 7.4 (37°C) while exhibiting a higher stability at pH < 7. The rate of the non‐enzymatic hydrolysis at pH 7.4 is dependent on steric and electronic effects which can be contributed to the particular acyloxy‐rest.