Premium
Synthesis of 4‐Methylthio Analogues of FLT and AZT and their Evaluation against HIV
Author(s) -
AbdelRahman Adel A.H.,
AbdelBary Hamed M.,
Pedersen Erik B.,
Nielsen Claus
Publication year - 1995
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.19953280112
Subject(s) - human immunodeficiency virus (hiv) , chemistry , pharmacology , stereochemistry , virology , medicine
Silylated 4‐methylthiouracil and 4‐methylthiothymine were condensed in the presence of TMS triflate with methyl 2,3‐dideoxy‐3‐fluoro‐5‐ O ‐(4‐phenylbenzoyl)‐D‐ erythro ‐pentofuranoside ( 3 ) and methyl 3‐azido‐5‐ O ‐(tert‐butyldiphenylsilyl)‐2,3‐dideoxy‐D‐ erythro ‐pentofuroside ( 8 ), respectively, to give the corresponding nucleosides which were deprotected. The 3′‐azido nucleoside was reduced with triphenylphosphine to the corresponding 3′‐amino nucleoside. The 3′‐amino nucleoside was also obtained by condensation of 4‐methylthiothymidine with a 3‐phthalimido sugar 14 followed by deprotection. The 4‐methylthio analogue 11 of AZT showed moderate activity against HIV.