STEREOSPECIFIC SYNTHESIS AND ANTI-HIV ACTIVITY OF (Z)2'-DEOXY-2'(3')-C-(CHLOROMETHYLENE) AND (E)3'-DEOXY-2'(3')-C-(CHLOROMETHYLENE) PYRIMIDINE NUCLEOSIDES

Authors
KALINICHENKO EN RUBINOVA EB BORISOV EV BALZARINI J DECLERCQ E MIKHAILOPULO IA
Citation
En. Kalinichenko et al., STEREOSPECIFIC SYNTHESIS AND ANTI-HIV ACTIVITY OF (Z)2'-DEOXY-2'(3')-C-(CHLOROMETHYLENE) AND (E)3'-DEOXY-2'(3')-C-(CHLOROMETHYLENE) PYRIMIDINE NUCLEOSIDES, Nucleosides & nucleotides, 14(3-5), 1995, pp. 533-536
Citations number
11
Categorie Soggetti
Biology
Journal title
Nucleosides & nucleotides → ACNP
ISSN journal
07328311
Volume
14
Issue
3-5
Year of publication
1995
Pages
533 - 536
Database
ISI
SICI code
0732-8311(1995)14:3-5<533:SSAAAO>2.0.ZU;2-M
Abstract
Reaction of 1-[2,5(and 3,5)-di-O-trityl-beta-D-erythro-pentofuran-3(an d 2)-ulosyl]uracil derivatives 5 and 6 with (chloromethyl)triphenylpho sphorane resulted in the stereoselective formation of (E)-3'- and (Z)- 2'-chloromethylene derivatives 7 (69%) and 8 (53%), respectively, depr otection of which gave 9 and 10. Transformation of the uracil nucleosi de 7 into cytosine one followed by deprotection yielded 12. The latter was converted into the arabinoside 14. The fully deprotected chlorome thylene nucleosides were tested for their activity against HIV-1 and H IV-2.