Synthesis and pharmacological evaluation of dual acting antioxidant A2A adenosine receptor agonists

Nicholas Hausler, Shane Devine, Fiona Michelle McRobb, Lyndon Warfe, Colin William Pouton, John Michael Haynes, Steven Eric Bottle, Paul James White, Peter John Scammells

Research output: Contribution to journalArticleResearchpeer-review

18 Citations (Scopus)

Abstract

A series of adenosine-5 -N-alkylcarboxamides and N-6-(2,2-diphenylethyl)adenosine-5 -N-alkylcarboxamides bearing antioxidant moieties in the 2-position were synthesized from the versatile intermediate, O-6-(benzotriazol-1-yl)-2-fluoro-2 ,3 -O-isopropylideneinosine-5 -N-alkylcarboxamide (1). These compounds were evaluated as A(2A) adenosine receptor (A(2A)R) agonists in a cAMP accumulation assay, and a number of potent and selective agonists were identified. Three of these compounds were evaluated further in an ischemic injury cell survival assay and a reactive oxygen species (ROS) production assay whereby 15b and 15c were shown to reduce ROS activity and cell death due to ischemia.
Original languageEnglish
Pages (from-to)3521 - 3534
Number of pages14
JournalJournal of Medicinal Chemistry
Volume55
Issue number7
DOIs
Publication statusPublished - 2012

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