Synthesis and biologic activity of purine 2'-deoxy-2’-fluoro-ni&>nucleosides

Academic Article

Abstract

  • The synthesis of 3,5-di-0-benzoyl-2-deoxy-2-fluoro-D-ribofuranosyl bromide (8) and its reaction with 2,6-dichloropurine by fusion and with mercuric cyanide catalysis is described. The resulting 2,6-dichloro-9-(3,5-di-0-benzoyl-2-deoxy-2-fluoro-j3-D-ribofuranosyl)purine (13) was converted to the 2-fluoroadenine (16), the 2-chloroadenine (17), 2,6-diaminopurine (12), and guanine (14) nucleosides by standard procedures. These nucleosides were cytotoxic to a number of cell lines in culture. The 2-haloadenine nucleosides 16 and 17 gave modest increases in lifespan when tested against the P388 leukemia in mice. © 1994, Taylor & Francis Group, LLC. All rights reserved.
  • Published In

    Digital Object Identifier (doi)

    Pubmed Id

  • 11116055
  • Start Page

  • 309
  • End Page

  • 323
  • Volume

  • 13
  • Issue

  • 1-3