Synthesis of 4'-Thionucleosides as Antitumor and Antiviral Agents

Chem Pharm Bull (Tokyo). 2018;66(2):139-146. doi: 10.1248/cpb.c17-00636.

Abstract

Many attempts have been made to synthesize structurally novel nucleoside derivatives in order to identify effective compounds for the treatment of tumors and virus-caused disease. At our laboratories, as part of our efforts to synthesize 4'-thionucleosides, we have identified and characterized biologically active nucleosides. During the course of our synthetic study, we developed the Pummerer-type thioglycosylation reaction. As a result, we synthesized a potent antineoplastic nucleoside, 1-(2-deoxy-2-fluoro-β-D-4-thio-arabino-furanosyl)cytosine (4'-thioFAC), and several novel 4'-thionucleosides that possess antiherpes virus activities.

Keywords: 4′-thionucleoside; Pummerer reaction; antiherpes virus; antitumor; antiviral; nucleoside.

Publication types

  • Review

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacology*
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / pharmacology*
  • Drug Design
  • Humans
  • Molecular Structure
  • Structure-Activity Relationship
  • Thionucleosides / chemical synthesis*
  • Thionucleosides / pharmacology*

Substances

  • Antineoplastic Agents
  • Antiviral Agents
  • Thionucleosides