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Synthesis and antiviral evaluation of quinazoline, thieno-[2,3-d]pyrimidine, and lumazine analogues of 3′-fluoro-3′-deoxythymidine (FLT)

✍ Scribed by El-Barbary, Ahmed A. ;El-Brollosy, Nasser R. ;Abdel-Bary, Hamed M. ;Pedersen, Erik B. ;Stein, Paul ;Nielsen, Claus

Publisher
John Wiley and Sons
Year
1995
Tongue
English
Weight
539 KB
Volume
1995
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

2,4(1__H__,3__H__)‐Quinazolinediones 3a–c, lumazine (3d) and thieno[2,3‐d]pyrimidine‐2,4(1__H__,3__H__)‐dione (8) were silylated and condensed with methyl 2,3‐dideoxy‐3‐fluoro‐5‐O‐(4‐phenylbenzoyl)‐β‐D‐erythro‐pentofuranoside (2) by using trimethylsilyl triflate as a catalyst to afford the corresponding cyclic nucleosides 4 and 9 and acyclic nucleosides 5 and 10. Removal of the protecting group from the glycon moiety was achieved in good yields by treatment with sodium methoxide in methanol at room temperature. The new FLT analogues were devoid of activity against HIV‐1 and HSV‐1.

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