N6-substituted C5'-modified adenosines as A1 adenosine receptor agonists

Bioorg Med Chem. 2008 Feb 15;16(4):1861-73. doi: 10.1016/j.bmc.2007.11.010. Epub 2007 Nov 6.

Abstract

Adenosines bearing 5'-modification in conjunction with an N6-substituent have previously been shown to act as partial agonists at the A1 adenosine receptor. Our current work investigates the effect of modifying the 5'-position in conjunction with efficacious bicyclic and tricyclic N6-substituents. Several highly potent agonists for the A1 adenosine receptor were identified; however, all of these compounds behaved as full agonists. In keeping with previous reports, 5'-halogen and 5'-sulfide derivatives of N6-(endo-norborn-2-yl)adenosine were, in general, low nanomolar agonists of the A1 adenosine receptor. The known partial agonist, N6-cyclopentyl-5'-deoxy-5'-ethylthioadenosine (2), also behaved as a full agonist in our assay.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine / analogs & derivatives*
  • Adenosine / chemistry
  • Adenosine / pharmacology*
  • Adenosine A1 Receptor Agonists*
  • Heterocyclic Compounds, 2-Ring
  • Heterocyclic Compounds, 3-Ring
  • Humans
  • Structure-Activity Relationship

Substances

  • Adenosine A1 Receptor Agonists
  • Heterocyclic Compounds, 2-Ring
  • Heterocyclic Compounds, 3-Ring
  • Adenosine