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N(6)-[(hetero)aryl/(cyclo)alkyl-carbamoyl-methoxy-phenyl]-(2-chloro)-5'-N-ethylcarboxamido-adenosines: the first example of adenosine-related structures with potent agonist activity at the human A(2B) adenosine receptor.

Authors
  • Baraldi, Pier Giovanni
  • Preti, Delia
  • Tabrizi, Mojgan Aghazadeh
  • Fruttarolo, Francesca
  • Saponaro, Giulia
  • Baraldi, Stefania
  • Romagnoli, Romeo
  • Moorman, Allan R
  • Gessi, Stefania
  • Varani, Katia
  • Borea, Pier Andrea
Type
Published Article
Journal
Bioorganic & Medicinal Chemistry
Publisher
Elsevier
Publication Date
Apr 01, 2007
Volume
15
Issue
7
Pages
2514–2527
Identifiers
PMID: 17306548
Source
Medline
License
Unknown

Abstract

A new series of N(6)-[(hetero)aryl/(cyclo)alkyl-carbamoyl-methoxy-phenyl]-(2-chloro)-5'-N-ethylcarboxamido-adenosines (24-43) has been synthesised and tested in binding assays at hA(1), hA(2A) and hA(3) adenosine receptors, and in a functional assay at the hA(2B) subtype. The examined compounds displayed high potency in activating A(2B) receptors with good selectivity versus A(2A) subtypes. The introduction of an unsubstituted 4-[(phenylcarbamoyl)-methoxy]-phenyl chain at the N(6) position of 5'-N-ethylcarboxamido-adenosine led us to the recognition of compound 24 as a full agonist displaying the highest efficacy of the series (EC(50) hA(2B)=7.3 nM). These compounds represent the first report about adenosine-related structures capable of activating hA(2B) subtype in the low nanomolar range.

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