163042-95-3

Upstream product

• 107-46-0 Hexamethyldisiloxane 
• 120046-86-8 2-chloro-N-⁶-(3-iodobenzyl)adenine 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 5451-40-1 2,6 dichloropurine 
• 3718-88-5 3-iodobenzylamine hydrochloride 

Downstream Products

• 163152-42-9 2-chloro-N⁶-(3-iodobenzyl)-9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)adenine 
• 163152-31-6 MRS 542 
• 163042-96-4 1-[2-chloro-6-[[(3-iodophenyl)methyl]amino]-9H-purin-9-yl]-1-deoxy-N-methyl-β-D-ribofuranuronamide 
• 874882-65-2 Thiocarbonic acid O-{(2R,3R,5S)-2-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-5-methylcarbamoyl-tetrahydro-furan-3-yl} ester O-phenyl ester 
• 163042-86-2 2-chloro-9-<3-deoxy-2-(methylsulfonyl)-5-(methylcarbamoyl)-β-D-ribofuranosyl>-N⁶-(3-iodobenzyl)adenine 
• 163042-82-8 9-<2-azido-2,3-dideoxy-5-(methylcarbamoyl)-β-D-arabinofuranosyl>-2-chloro-N⁶-(3-iodobenzyl)adenine 
• 163042-87-3 2-chloro-9-<3-deoxy-5-(methylcarbamoyl)-β-D-ribofuranosyl>-N⁶-(3-iodobenzyl)adenine 
• 163042-85-1 9-<2-acetyl-3-deoxy-5-(methylcarbamoyl)-β-D-ribofuranosyl>-2-chloro-N⁶-(3-iodobenzyl)adenine 
• 163042-90-8 2-chloro-N⁶-(3-iodobenzyl)-9-<5-(methylcarbamoyl)-2,3-di-O-benzoyl-β-D-ribofuranosyl>adenine 

Relevant academic research and scientific papers

Structure-Activity Relationships of 9-Alkyladenine and Ribose-Modified Adenosine Derivatives at Rat A3 Adenosine Receptors

9-Alkyladenine derivatives and ribose-modified N6-benzyladenosine derivatives were synthesized in an effort to identify selective ligands for the rat A3 adenosine receptor and leads for the development of antagonists.The derivatives

2-Substitution of N6-benzyladenosine-5'-uronamides enhances selectivity for A3 adenosine receptors

Adenosine derivatives bearing an N6-(3-iodobenzyl) group, reported to enhance the affinity of adenosine-5'-uronamide analogues as agonists at A3 adenosine receptors (J. Med. Chem. 1994, 37, 636-646), were synthesized starting from methyl β-D-ribofuranoside in 10 steps. Binding affinities at A1 and A(2a) receptors in rat brain membranes and at cloned rat A3 receptors from stably transfected CHO cells were compared. N6-(3- Iodobenzyl)adenosine was 2-fold selective for A3 vs A1 or A(2a) receptors; thus it is the first monosubstituted adenosine analogue having any A3 selectivity. The effects of 2-substitution in combination with modifications at the N6- and 5'-positions were explored. 2-Chloro-N6-(3- iodobenzyl)adenosine had a K(i) value of 1.4 nM and moderate selectivity for A3 receptors. 2-Chloro-N6-(3-iodobenzyl)adenosine-5'-N-methyluronamide, which displayed a K(i) value of 0.33 nM, was selective for A3 vs A1 and A(2a) receptors by 2500- and 1400-fold, respectively. It was 46,000-fold selective for A3 receptors vs the Na+-independent adenosine transporter, as indicated in displacement of [3H]N6-(4-nitrobenzyl)-thioinosine binding in rat brain membranes. In a functional assay in CHO cells, it inhibited adenylate cyclase via rat A3 receptors with an IC50 of 67 nM. 2- (Methylthio)-N6-(3-iodobenzyl)-adenosine-5'-N-methyluronamide and 2- (methylamino)-N6-(3-iodobenzyl)adenosine-5'-N-methyluronamide were less potent, but nearly as selective for A3 receptors. Thus, 2-substitution (both small and sterically bulky) is well-tolerated at A3 receptors, and its A3 affinity-enhancing effects are additive with effects of uronamides at the 5'- position and a 3-iodobenzyl group at the N6-position.