SYNTHESIS AND ANTI-HIV ACTIVITY OF 2-SUBSTITUTED 2'-DEOXY-2'-FLUOROADENOSINES

Authors
MARUYAMA T UTSUMI K SATO Y RICHMAN DD
Citation
T. Maruyama et al., SYNTHESIS AND ANTI-HIV ACTIVITY OF 2-SUBSTITUTED 2'-DEOXY-2'-FLUOROADENOSINES, Nucleosides & nucleotides, 13(6-7), 1994, pp. 1219-1230
Citations number
8
Categorie Soggetti
Biology
Journal title
Nucleosides & nucleotides → ACNP
ISSN journal
07328311
Volume
13
Issue
6-7
Year of publication
1994
Pages
1219 - 1230
Database
ISI
SICI code
0732-8311(1994)13:6-7<1219:SAAAO2>2.0.ZU;2-A
Abstract
2-Iodo-6-methoxypurine 2'-deoxy-2'-fluororiboside 8 was prepared from 2-iodo-6-methoxypurine riboside 1 in 8 steps. Reaction of 8 with ammon ia in methanol gave the 2-iodoadenosine derivative 9 in 69% yield. Tre atment of 9 with various nucleophiles gave 2-substituted analogues of 2'-deoxy-2'-fluoroadenosine 10-12. 2'-Deoxy-2,2'-difluoroadenosine 14 was also prepared by the treatment of the quaternary salt 13 with fluo ride ion, but similar reactions of 13 with chloride or bromide ion gav e the corresponding piperidine congeners 15a,b.