14426-53-0

Basic information

• Product Name: 6-iodo-9-pentofuranosyl-9H-purine
• Synonyms: 9H-purine, 6-iodo-9-pentofuranosyl-
• CAS NO: 14426-53-0
• Molecular Formula: C₁₀H₁₁IN₄O₄
• Molecular Weight: 378.1232
• Mol File: 14426-53-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 648.2°C at 760 mmHg
• Flash Point: 345.8°C
• Density: 2.53g/cm³
• Vapor Pressure: 1.09E-17mmHg at 25°C
• Refractive Index: 1.925
• CAS DataBase Reference: 6-iodo-9-pentofuranosyl-9H-purine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-iodo-9-pentofuranosyl-9H-purine(14426-53-0)
• EPA Substance Registry System: 6-iodo-9-pentofuranosyl-9H-purine(14426-53-0)

Safety Data

• Hazardous Substances Data: 14426-53-0(Hazardous Substances Data)

Upstream product

• 5987-74-6 6-iodo-9-[β-(2',3',5'-tri-O-acetyl)-D-ribofuranosyl]purine 
• 58-61-7 adenosine 
• 2545-26-8 6-iodopurine 
• 58-96-8 uridine 
• 7387-57-7 triacetyladenosine 

Downstream Products

• 1867-73-8 N⁶-methyladenosine 
• 41552-82-3 N-cyclopentyladenosine 
• 68715-65-1 N⁶-amino-N⁶-methyladenosine 
• 65134-53-4 9-β-D-ribofuranosylpurine-6-carboxamide 

Relevant articles and documents

Synthesis and ability of new ligands for G protein-coupled receptors 17 (GPR17)

Background: GPR17 is believed to be a novel target for the development of new therapeutic approaches to human stroke and multiple sclerosis. Hence, the selection of GPR17 ligands may be a potent way to reduce the progression of ischemic damage. Material/Methods: New potential ligands for GPR17, mono-, di-, and triphosphate adenosine nucleotides substituted at N6-position with a methyl and a cyclopentyl group were synthesized. The ability of new ligands to bind GPR17 was evaluated using frontal affinity chromatography-mass spectrometry (FAC-MS) method. Cangrelor, MRS2179, and uridine diphosphate were selected as the reference compounds. Results: The new triphosphate derivatives 9 and 10 were considered as the new GPR17 ligands. The compound 10 was eluted with breakthrough time (bt) between cangrelor and MRS 2179 (compound 10, bt=12.25; cangrelor, bt=24.55, and MRS 2179, bt=7.10), while the breakthrough volume of compound 9 was similar to that of MRS 2179 (compound 9, bt=7.53 and MRS 2179, bt=7.10). Conclusions: N6-cyclopentyATP 10 is medium-high affinity ligand of GPR17, while the corresponding N6-methyl derivative 9 is a medium affinity ligand similar to MRS 2179. Hence, the new N6-cyclopentylATP 10 might be a good candidate for the pharmacological characterization of GPR17.

Nucleic acid related compounds. 116. Nonaqueous diazotization of aminopurine nucleosides. Mechanistic considerations and efficient procedures with tert-butyl nitrite or sodium nitrite

Nonaqueous diazotization-dediazoniation of two types of aminopurine nucleoside derivatives has been investigated. Treatment of 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2-amino-6-chloropurine (1) with SbCl3/CH2Cl2 was examined with benzyltriethylammonium (BTEA) chloride as a soluble halide source and tert-butyl nitrite (TBN) or sodium nitrite as the diazotization reagent. Optimized yields (>80%) of the 2,6-dichloropurine derivative were obtained with SbCl3. Combinations with SbBr3/CH2Br2 gave the 2-bromo-6-chloropurine product (>60%), and SbI3/CH2I2/THF gave the 2-iodo-6-chloropurine derivative (>45%). Antimony trihalide catalysis was highly beneficial. Mixed combinations (SbX3/CH2X′2; X/X′ = Bt/Cl) gave mixtures of 2-(bromo, chloro, and hydro)-6- chloropurine derivatives that were dependent on reaction conditions. Addition of iodoacetic acid (IAA) resulted in diversion of purine radical species into a 2-iodo-6-chloropurine derivative with commensurate loss of other radical-derived products. This allowed evaluation of the efficiency of SbX3-promoted cation-derived dediazoniations relative to radical-derived reactions. Efficient conversions of adenosine, 2′-deoxyadenosine, and related adenine nucleosides into 6-halopurine derivatives of current interest were developed with analogous combinations.