Pyrrolo[2,3-d]pyrimidine nucleosides: synthesis and antitumor activity of 7-substituted 7-deaza-2'-deoxyadenosines

Nucleosides Nucleotides Nucleic Acids. 2000 Jan-Feb;19(1-2):237-51. doi: 10.1080/15257770008033006.

Abstract

A one step synthesis, using the nucleoside 7-iodo-2'-deoxytubercidin (2b) in a Pd(0)/Cu(I)-catalyzed cross coupling reaction furnished a series of 7-alkynyl-2'-deoxytubercidin derivatives. The 7-iodo-, 7-chloro- or 7-bromo 2'-deoxytubercidins 2b-d as well as certain 7-alkynyl derivatives show significant activity against several tumor cell lines, with 7-iodo-2'-deoxytubercidin (2b) as the most effective compound.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Catalysis
  • Copper
  • Drug Screening Assays, Antitumor
  • Humans
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Mice
  • Palladium
  • Pyrimidine Nucleosides / chemical synthesis*
  • Pyrimidine Nucleosides / chemistry
  • Pyrimidine Nucleosides / pharmacology
  • Tubercidin / analogs & derivatives*
  • Tubercidin / chemical synthesis*
  • Tubercidin / chemistry
  • Tubercidin / pharmacology
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents
  • Pyrimidine Nucleosides
  • Palladium
  • Copper
  • Tubercidin