120046-86-8

Basic information

• Product Name: 1H-Purin-6-amine, 2-chloro-N-[(3-iodophenyl)methyl]-
• CAS NO: 120046-86-8
• Molecular Formula: C12H9ClIN5
• Molecular Weight: 385.594
• Mol File: 120046-86-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1H-Purin-6-amine, 2-chloro-N-[(3-iodophenyl)methyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Purin-6-amine, 2-chloro-N-[(3-iodophenyl)methyl]-(120046-86-8)
• EPA Substance Registry System: 1H-Purin-6-amine, 2-chloro-N-[(3-iodophenyl)methyl]-(120046-86-8)

Safety Data

• Hazardous Substances Data: 120046-86-8(Hazardous Substances Data)

Usage

Purine derivative

The compound is derived from purine, which is a key structural motif in many biologically active molecules.

Chlorine atom

The presence of a chlorine atom in the compound may contribute to its pharmacological properties.

Iodophenylmethyl group

The compound contains an iodophenylmethyl group, which is a substituted phenyl ring with an iodine atom attached to a methyl group.

Potential importance in medicinal chemistry

Due to its purine core and unique substituents, this compound may be valuable for further research and development in drug discovery.

Pharmacological properties

The presence of chlorine and iodine in the molecule may contribute to its pharmacological properties, making it a potentially valuable candidate for drug development.

Upstream product

• 3718-88-5 3-iodobenzylamine hydrochloride 
• 5451-40-1 2,6 dichloropurine 

Downstream Products

• 163042-95-3 (2-Chloro-9-trimethylsilanyl-9H-purin-6-yl)-(3-iodo-benzyl)-amine 
• 551929-66-9 (2R,3S,4S,5R)-4-Benzoyloxy-5-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-3-fluoro-tetrahydro-furan-2-carboxylic acid methyl ester 
• 163152-42-9 2-chloro-N⁶-(3-iodobenzyl)-9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)adenine 
• 163042-90-8 2-chloro-N⁶-(3-iodobenzyl)-9-<5-(methylcarbamoyl)-2,3-di-O-benzoyl-β-D-ribofuranosyl>adenine 
• 163042-96-4 1-[2-chloro-6-[[(3-iodophenyl)methyl]amino]-9H-purin-9-yl]-1-deoxy-N-methyl-β-D-ribofuranuronamide 
• 163152-31-6 MRS 542 
• 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 
• 163042-85-1 9-<2-acetyl-3-deoxy-5-(methylcarbamoyl)-β-D-ribofuranosyl>-2-chloro-N⁶-(3-iodobenzyl)adenine 
• 163042-87-3 2-chloro-9-<3-deoxy-5-(methylcarbamoyl)-β-D-ribofuranosyl>-N⁶-(3-iodobenzyl)adenine 
• 163042-77-1 (2R,3R,4R)-2-(2-chloro-6-(3-iodobenzylamino)-9H-purin-9-yl)-tetrahydrofuran-3,4-diol 

Relevant articles and documents

Preparation of nucleoside uronamides as A3 adenosine receptor agonists.

The present invention provides N 6-benzyladenosine-5'-N-uronamide and related substituted compounds, particularly those containing substituents on the benzyl and/or uronamide groups, and modified xanthine ribosides, as well as pharmaceutical compositions containing such compounds. The present invention also provides a method of selectively activating an A 3 adenosine receptor in a mammal, which method comprises acutely or chronically administering to a mammal in need of selective activation of its A 3 adenosine receptor a therapeutically effective amount of a compound which binds with the A. sub.3 receptor so as to stimulate an A 3 receptor-dependent response.

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.