PMID: 2096797Dec 1, 1990Paper

Synthesis of 3'-(4-nitroimidazol-1-yl)-2',3'-dideoxynucleosides of pyrimidine analogues and their biological evaluation against HIV

Archiv der Pharmazie
M S MotawiaC Nielsen

Abstract

Reaction of 1,5-di-O-acetyl-2,3-dideoxy-3-phthalimido-beta-D-erythro-pento-fur anose (1) with silylated pyrimidinediones 2a-c using the Lewis acid trimethylsilyl triflate as catalyst afforded nucleosides 3a-c and 4a,c which were deprotected with 33% methylamine/ethanol to give the corresponding 3-aminonucleosides 5a-c and 6. These were reacted with 1,4-dinitroimidazoles 7a,b to give the 3-imidazolyldideoxynucleosides 8a,b and 9a-f. At sub-toxic concentrations these compounds were ineffective against HIV-1.

References

Feb 4, 1987·Nature·H Mitsuya, S Broder
May 1, 1987·Journal of Medicinal Chemistry·C H KimJ S Driscoll
Dec 18, 1986·The New England Journal of Medicine·R E ChaissonP A Volberding
Aug 1, 1987·Journal of Medicinal Chemistry·P HerdewijnH Vanderhaeghe
Jun 1, 1983·Journal of Medicinal Chemistry·T A KrenitskyJ W Selway

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