Synthesis of purine homo-N-nucleosides modified with coumarins as free radicals scavengers

J Enzyme Inhib Med Chem. 2013 Aug;28(4):765-75. doi: 10.3109/14756366.2012.684050. Epub 2012 May 16.

Abstract

Cross metathesis (CM) of 9-butenylpurines with 4-butenyloxycoumarin in the presence of Grubbs 2nd generation catalyst under MW irradiation resulted to conjugated compounds containing homo-N-nucleosides and coumarins. Analogous derivatives received by the CM reaction of 9-butenyl-6-piperidinylpurine with 6- or 7-butenyloxycoumarins, allyloxycoumarins or coumarinyl acrylate. These compounds were tested in vitro for their antioxidant activity and they present significant scavenging activity. The presence of a pentenyloxy moiety, the attachment position on coumarin ring as well as a purine homo-N-nucleoside group are considered as important structural features.

MeSH terms

  • Coumarins / chemistry*
  • Free Radical Scavengers / chemical synthesis*
  • Free Radical Scavengers / chemistry
  • Molecular Structure
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry
  • Purines / chemistry*

Substances

  • Coumarins
  • Free Radical Scavengers
  • Nucleosides
  • Purines
  • purine