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

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Abstrakt

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.

OriginalsprogEngelsk
TidsskriftLiebigs Annalen
Vol/bind1995
Udgave nummer7
Sider (fra-til)1371-1375
Antal sider5
ISSN0947-3440
DOI
StatusUdgivet - 23. jun. 1995

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