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2‐Nucleos‐5′‐ O ‐yl‐4 H ‐1,3,2‐benzodioxaphos‐phinin‐2‐oxides—A New Concept for Lipophilic, Potential Prodrugs of Biologically Active Nucleoside Monophosphates
Author(s) -
Meier Chris
Publication year - 1996
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199600701
Subject(s) - prodrug , nucleoside , chemistry , hydrolysis , nucleoside analogue , stereochemistry , combinatorial chemistry , biochemistry
A nonenzymatic, hydrolytic tandem reaction selectively releases the 5′‐phosphorylated derivatives of the antiviral active nucleoside analogues ddT and d4T from the nucleoside phosphotriesters 1 and 2 . The hydrolysis of 1 and 2 can be controlled by varying the substituents X . Consequently, compounds of type 1 and 2 should, in principle, be suitable prodrugs of phosphorylated nucleosides.