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

Ahmed A. El‐Barbary, Nasser R. El‐Brollosy, Hamed M. Abdel‐Bary, Erik B. Pedersen*, Paul Stein, Claus Nielsen

*Corresponding author for this work

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

2,4(1H,3H)‐Quinazolinediones 3a–c, lumazine (3d) and thieno[2,3‐d]pyrimidine‐2,4(1H,3H)‐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.

Original languageEnglish
JournalLiebigs Annalen
Volume1995
Issue number7
Pages (from-to)1371-1375
Number of pages5
ISSN0947-3440
DOIs
Publication statusPublished - 23. Jun 1995

Keywords

  • 3′‐Fluoronucleosides
  • FLT analogues
  • HIV
  • Nucleosides

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