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The Potential of Aspirin in Prodrug Synthesis: A New Potential Delivery System of AZT and FLT
Author(s) -
Zahran Magdy A.,
Kovács Lajos,
Sakka Ibrahim El,
Pedersen Erik B.,
Nielsen Claus
Publication year - 1996
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.19963290809
Subject(s) - prodrug , chemistry , aspirin , trifluoroacetic acid , hydrolysis , trifluoroacetic anhydride , acetylation , human immunodeficiency virus (hiv) , pharmacology , combinatorial chemistry , stereochemistry , biochemistry , organic chemistry , medicine , virology , gene
Abstract Aspirin ( O ‐acetylsalicylic acid) has been used to synthesize prodrugs of 3′‐azido‐3′‐deoxythymidine (AZT) and 3′‐deoxy‐3′‐fluorothymidine (FLT). The mixed anhydride between aspirin and trifluoroacetic acid was synthesized and reacted with AZT and FLT to give the blocked nucleosides attached through the 5′‐ O position to the 2‐position of 2‐methyl‐4 H ‐1,3‐benzodioxin‐4‐one. The prodrugs showed the same activities against HIV‐1 in MT‐4 cells as the original drugs. Hydrolysis of the synthesized prodrugs in the growth medium, used for anti‐HIV investigations, resulted in formation of 5‐ O acetylated drugs which were subsequently hydrolyzed into the original drugs.