Synthesis of substituted 6-cyclopropylpurine bases and nucleosides by cross-coupling reactions or cyclopropanations

Org Biomol Chem. 2008 Jul 7;6(13):2377-87. doi: 10.1039/b802833h. Epub 2008 May 2.

Abstract

Synthesis of novel purine bases and nucleosides bearing unsubstituted or substituted cyclopropyl rings in position 6 is reported. Unsubstituted 6-cyclopropylpurines were efficiently prepared by cross-coupling reactions of 6-chloropurines with cyclopropylzinc chloride. 6-Vinylpurines underwent Cu-mediated cyclopropanations with ethyl diazoacetate to give 6-[(ethoxycarbonyl)cyclopropyl]purines that were further transformed to carboxylic acids, amides and alcohols. 6-Cyclopropylpurine ribonucleoside exerted a significant cytostatic effect while all substituted derivatives were inactive.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Crystallography, X-Ray
  • Cyclopropanes / chemistry*
  • Humans
  • Mice
  • Purine Nucleosides / chemical synthesis*
  • Purine Nucleosides / chemistry
  • Purine Nucleosides / pharmacology*

Substances

  • Cyclopropanes
  • Purine Nucleosides