Synthesis of 8-(cyclopentyloxy)phenyl substituted xanthine derivatives as adenosine A2A ligands

Ranju Bansal, Gulshan Kumar, Deepika Gandhi, Rakesh Yadav, Louise C Young, Alan L Harvey

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

The present paper describes the synthesis of a series of 8-(cyclopentyloxy)phenyl-xanthines and their evaluation for affinity for A1 and A2 adenosine receptors using radioligand binding assays. The effects of moving the cyclopentyloxy substituent with or without an ortho methoxy group on the various positions of the 8-phenyl ring have been studied. The vanilloid based xanthines 8-[4-(cyclopentyloxy)-3-methoxyphenyl]-1,3-dimethylxanthine (6a) (K(i)= 100 nM) and 8-[(4-cyclopentyloxy)-3-methoxyphenyl] -3-methyl-1-propylxanthine (12) (K(i) = 150 nM) displayed the highest affinity at A2A receptors as well as over 1000 fold selectivity over the A1 adenosine receptor subtype.
Original languageEnglish
Pages (from-to)131-136
Number of pages6
JournalArzneimittel Forschung
Volume60
Issue number3
Publication statusPublished - 2010

Keywords

  • anti-asthmatic agents
  • humans
  • indicators and reagents
  • magnetic resonance spectroscopy
  • radioligand assay
  • receptor
  • spectrophotometry
  • spectroscopy
  • structure-activity relationship
  • xanthine
  • adenosine A1
  • adenosine A2A
  • infrared
  • fourier rransform infrared

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