Stereospecific synthesis and biological evaluations of beta-L-pentofuranonucleoside derivatives of 5-fluorouracil and 5-fluorocytosine

Eur J Med Chem. 2001 May;36(5):447-60. doi: 10.1016/s0223-5234(01)01238-7.

Abstract

In the search for new chemotherapeutic agents, we have focused our work on the synthesis and the study of several unnatural beta-L-nucleoside analogues. In this paper, we report on the synthesis of beta-L-pentofuranonucleosides (and their 2'-deoxy derivatives) of 5-fluorouracil and their inhibitory effects on the proliferation of several murine and human tumor cells. The corresponding 5-fluorocytosine derivatives were also synthesized and their anti-HIV and anti-HBV activities have been evaluated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-HIV Agents / pharmacology
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Antineoplastic Agents / toxicity
  • Cell Division / drug effects
  • Drug Design
  • Flucytosine / analogs & derivatives*
  • Fluorouracil / analogs & derivatives*
  • HIV / drug effects
  • Humans
  • Mice
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry
  • Nucleosides / pharmacology*
  • Nucleosides / toxicity
  • Stereoisomerism
  • Structure-Activity Relationship
  • T-Lymphocytes / cytology
  • T-Lymphocytes / drug effects
  • T-Lymphocytes / immunology
  • Tumor Cells, Cultured

Substances

  • Anti-HIV Agents
  • Antineoplastic Agents
  • Nucleosides
  • Flucytosine
  • Fluorouracil