750644-54-3

Basic information

• Product Name: (2R,3S,4S,5R)-9-(3,4-dihydroxy-5-hydroxymethyl-tetrahydrofuran-2-yl)-6-(2-phenyl-cyclopropylamino)-9H-purine-2-carbonitrile
• Synonyms: (2R,3S,4S,5R)-9-(3,4-dihydroxy-5-hydroxymethyl-tetrahydrofuran-2-yl)-6-(2-phenyl-cyclopropylamino)-9H-purine-2-carbonitrile
• CAS NO: 750644-54-3
• Molecular Weight: 408.417
• Mol File: 750644-54-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,3S,4S,5R)-9-(3,4-dihydroxy-5-hydroxymethyl-tetrahydrofuran-2-yl)-6-(2-phenyl-cyclopropylamino)-9H-purine-2-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,4S,5R)-9-(3,4-dihydroxy-5-hydroxymethyl-tetrahydrofuran-2-yl)-6-(2-phenyl-cyclopropylamino)-9H-purine-2-carbonitrile(750644-54-3)
• EPA Substance Registry System: (2R,3S,4S,5R)-9-(3,4-dihydroxy-5-hydroxymethyl-tetrahydrofuran-2-yl)-6-(2-phenyl-cyclopropylamino)-9H-purine-2-carbonitrile(750644-54-3)

Safety Data

• Hazardous Substances Data: 750644-54-3(Hazardous Substances Data)

Upstream product

• 1986-47-6 tranylcypromine hydrochloride 
• 333333-74-7 (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(6-chloro-2-cyano-9H-purin-9-yl)tetrahydro-3-furanyl acetate 
• 16321-99-6 2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine 
• 2004-07-1 2-Amino-6-chloropurine riboside 

Relevant articles and documents

Modulation of adenosine receptor affinity and intrinsic efficacy in adenine nucleosides substituted at the 2-position

We studied the structural determinants of binding affinity and efficacy of adenosine receptor (AR) agonists. Substituents at the 2-position of adenosine were combined with N6-substitutions known to enhance human A 3AR affinity. Selectivity of binding of the analogues and their functional effects on cAMP production were studied using recombinant human A1, A2A, A2B, and A3ARs. Mainly sterically small substituents at the 2-position modulated both the affinity and intrinsic efficacy at all subtypes. The 2-cyano group decreased hA3AR affinity and efficacy in the cases of N6-(3-iodobenzyl) and N 6-(trans-2-phenyl-1-cyclopropyl), for which a full A3AR agonist was converted into a selective antagonist; the 2-cyano-N 6-methyl analogue was a full A3AR agonist. The combination of N6-benzyl and various 2-substitutions (chloro, trifluoromethyl, and cyano) resulted in reduced efficacy at the A1AR. The environment surrounding the 2-position within the putative A3AR binding site was explored using rhodopsin-based homology modeling and ligand docking.