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Lipophilic 5′,5′‐ O ‐Dinucleoside‐α‐hydroxybenzylphosphonic Acid Esters as Potential Prodrugs of 2′,3′‐Dideoxythymidine (ddT)
Author(s) -
Meier Chris
Publication year - 1993
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.199317041
Subject(s) - prodrug , phosphonate , chemistry , aryl , nucleoside , cleavage (geology) , phosphate , nucleic acid , stereochemistry , organic chemistry , biochemistry , biology , alkyl , paleontology , fracture (geology)
Phosphonylated and phosphonylated derivatives of the antiviral active nucleoside analogue 2′,3′‐dideoxythymidine (ddT) can be released from the dinucleoside‐α‐hydroxybenzylphosphonic acid esters ( 1 ). Depending on the substituents at the aryl group, phosphonate–phosphate rearrangement or direct cleavage was observed. Consequently, compounds of type 1 can, in principle, serve as prodrugs of phosphorylated or phosphonylated nucleosides. Araryl.