Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis and Binding Affinity of Homologated Adenosine Analogues as A3 Adenosine Receptor Ligands

  • Lee, Hyuk-Woo (Department of Bioinspired Science and Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University) ;
  • Choi, Won-Jun (Department of Bioinspired Science and Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University) ;
  • Jacobson, Kenneth A. (Molecular Recognition Section, Laboratory of Bioorganic Chemistry, National Institute of Diabetic, Digestive Disease and Kidney Disease, National Institutes of Health) ;
  • Jeong, Lak-Shin (Department of Bioinspired Science and Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University)
  • Received : 2011.03.10
  • Accepted : 2011.03.25
  • Published : 2011.05.20
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Abstract

Homologated analogues 3a and 3b of potent and selective A3 adenosine receptor ligands, IB-MECA and dimethyl-IB-MECA were synthesized from commercially available 1-O-acetyl-2,3,5-tri-O-benzoyl-${\beta}$-D-ribofuranose (4) via $Co_2(CO)_8$-catalyzed siloxymethylation as a key step. Unfortunately, homologated analogues 3a and 3b did not show significant binding affinities at three subtypes of adenosine receptors, indicating that free rotation, resulting from homologation, induced unfavorable interactions in the binding site of the receptor maybe due to the presence of many conformations.

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References

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Cited by

  1. ChemInform Abstract: Synthesis and Binding Affinity of Homologated Adenosine Analogues as A3 Adenosine Receptor Ligands. vol.42, pp.43, 2011, https://doi.org/10.1002/chin.201143190