Stereospecific synthesis and anti-HIV activity of (Z)2'- and (E)3'- deoxy-2'(3')-C-(chloromethylene) pyrimidine nucleosides

Article abstract of DOI:10.1080/15257779508012420

Reaction of 1-[2,5(and 3,5)-di-O-trityl-β-D-erythro-pentofuran-3(and 2)- ulosyl]uracil derivatives 5 and 6 with (chloromethyl)triphenylphosphorane resulted in the stereoselective formation of (E)-3'- and (Z)-2'- chloromethylene derivatives 7 (69%) and 8 (53%), respectively, deprotection of which gave 9 and 10. Transformation of the uracil nucleoside 7 into cytosine one followed by deprotection yielded 12. The latter was convened into the arabinoside 14. The fully deprotected chloromethylene nucleosides were tested for their activity against HIV-1 and HIV-2.

Full text of DOI:10.1080/15257779508012420

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Stereospecific Synthesis and Anti-HIV
Activity of (Z)2′- and (E)3′-Deoxy-2′(3′)-
C-(chloromethylene) Pyrimidine
Nucleosides
Elena N. Kalinichenko a , Elena B. Rubinova a , Evgueny V. Borisov a
Jan Balzarini b , Erik De Clercq b & Igor A. Mikhailopulo a
a Institute of Bioorganic Chemistry, Byelorussian Academy of
Sciences , 220141, Minsk, Byelorussia
,
b Katholieke Universiteit Leuven, Rega Institute for Medical
Research , Minderbroedersstraat, 10, B-3000, Leuven, Belgium
Published online: 16 Feb 2007.
To cite this article: Elena N. Kalinichenko , Elena B. Rubinova , Evgueny V. Borisov , Jan Balzarini ,
Erik De Clercq & Igor A. Mikhailopulo (1995) Stereospecific Synthesis and Anti-HIV Activity of (Z)2′-
and (E)3′-Deoxy-2′(3′)-C-(chloromethylene) Pyrimidine Nucleosides, Nucleosides and Nucleotides,
14:3-5, 533-536
To link to this article: http://dx.doi.org/10.1080/15257779508012420
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