163152-31-6

Basic information

• Product Name: Adenosine, 2-chloro-N-[(3-iodophenyl)methyl]-
• CAS NO: 163152-31-6
• Molecular Formula: C17H17ClIN5O4
• Molecular Weight: 517.711
• Mol File: 163152-31-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Adenosine, 2-chloro-N-[(3-iodophenyl)methyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Adenosine, 2-chloro-N-[(3-iodophenyl)methyl]-(163152-31-6)
• EPA Substance Registry System: Adenosine, 2-chloro-N-[(3-iodophenyl)methyl]-(163152-31-6)

Safety Data

• Hazardous Substances Data: 163152-31-6(Hazardous Substances Data)

Upstream product

• 15373-23-6 (2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl dibenzoate 
• 163042-95-3 (2-Chloro-9-trimethylsilanyl-9H-purin-6-yl)-(3-iodo-benzyl)-amine 
• 3718-88-5 3-iodobenzylamine hydrochloride 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 163152-42-9 2-chloro-N⁶-(3-iodobenzyl)-9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)adenine 
• 120046-86-8 2-chloro-N-⁶-(3-iodobenzyl)adenine 
• 5451-40-1 2,6 dichloropurine 

Downstream Products

• 1000980-71-1 ((3aR,4R,6R,6aR)-6-(2-chloro-6-(3-iodobenzylamino)9H-purine-9-yl) 2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 163042-96-4 1-[2-chloro-6-[[(3-iodophenyl)methyl]amino]-9H-purin-9-yl]-1-deoxy-N-methyl-β-D-ribofuranuronamide 

Relevant articles and documents

Novel Adenine Derivatives and the Use Thereof

The present invention relates to a novel adenine derivative and a pharmaceutical use thereof and, more specifically, to a novel adenine derivative having a structure of chemical formula 1 or a pharmaceutically acceptable salt thereof, and to a composition containing the same for preventing or treating degenerative brain disease. The novel adenine derivative and the pharmaceutically acceptable salt thereof according to the present invention are adenosine A3 receptor agonists, and have an action of inhibiting the migration (or infiltration) of inflammatory cells (microglia, macrophages, neutrophils, etc.), to disease areas and the activities thereof. In addition, the adenine derivative according to the present invention was verified to suppress and treat brain injury more remarkably when compared with the known adenosine A3 receptor agonists in a cerebral ischemia experimental model, exhibit a significant effect by drug administration 10 hours after cerebral infarction, and allow long-term survival in spite of brain injury due to cerebral ischemia, and thus can be useful as an agent for treating and preventing degenerative brain disease including stroke.(AA,BB,CC,DD) Chemical formula 5COPYRIGHT KIPO 2015

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.