120225-53-8Relevant articles and documents
Synthesis and pharmacological evaluation of dual acting antioxidant a 2A adenosine receptor agonists
Hausler, Nicholas E.,Devine, Shane M.,McRobb, Fiona M.,Warfe, Lyndon,Pouton, Colin W.,Haynes, John M.,Bottle, Steven E.,White, Paul J.,Scammells, Peter J.
experimental part, p. 3521 - 3534 (2012/06/04)
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, O6-(benzotriazol-1-yl)-2-fluoro
Linear and convergent approaches to 2-substituted adenosine-5′-N-alkylcarboxamides
Foitzik, Richard C.,Devine, Shane M.,Hausler, Nicholas E.,Scammells, Peter J.
experimental part, p. 8851 - 8857 (2009/12/26)
Herein we report both linear and convergent pathways for the preparation of 2-alkynyl substituted adenosine-5′-N-ethylcarboxamides via the versatile synthetic intermediate, 2-iodoadenosine-5′-N-ethylcarboxamide (13). The linear approach afforded 13 in an overall yield of 30% from guanosine over eight synthetic steps. The convergent approach was shorter, but proceeded in lower yield (five steps, 20% yield). Both approaches compare favourably with previously reported syntheses of 13, which has been prepared in 15% yield from guanosine over nine steps. 2-Iodoadenosine-5′-N-ethylcarboxamide (13) was subsequently converted to HENECA (2) and PHPNECA (3) to exemplify the utility of this approach for the preparation of?potent A2A adenosine receptor agonists. The linear approach was also amenable to the synthesis of 2-fluoropurine ribosides, which were subsequently elaborated into 2-alkylaminoadenosine-5′-N-ethylcarboxamides. Furthermore, both of these synthetic approaches are readily amenable to the synthesis of adenosine analogues with varied 2-, 6- and 5′-substitution patterns.
2-(Arylalkylamino)adenosin-5'-uronamides: A New Class of Highly Selective Adenosine A2 Receptor Ligands
Hutchison, Alan J.,Williams, Michael,Jesus, Reynalda, de,Yokoyama, Rina,Oei, Howard H.,et al.
, p. 1919 - 1924 (2007/10/02)
The synthesis and receptor-binding profiles at adenosine receptor subtypes for a series of 2-(arylalkylamino)adenosin-5'-uronamides is described.Halogenated 2-phenethylamino analogues such as 3e show greater than 200-fold selectivity for the A2 receptor s
