✦ LIBER ✦

Synthesis of 4-Methylthio Analogues of FLT and AZT and their Evaluation against HIV

✍ Scribed by Adel A.-H. Abdel-Rahman; Hamed M. Abdel-Bary; Erik B. Pedersen; Claus Nielsen

Publisher: John Wiley and Sons
Year: 1995
Tongue: English
Weight: 392 KB
Volume: 328
Category: Article
ISSN: 0365-6233
DOI: 10.1002/ardp.19953280112

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

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.

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