2004-07-1

Basic information

• Product Name: 2-Amino-6-chloropurine-9-riboside
• Synonyms: 2-AMINO-6-CHLORO-9-(BETA-D-RIBOFURANOSYL)PURINE;2-AMINO-6-CHLOROPURINE-9-BETA-D-RIBOSIDE;2-AMINO-6-CHLOROPURINE-9-RIBOSIDE;2-AMINO-6-CHLOROPURINE RIBOSIDE;6-CHLOROADENOSINE;6-CHLOROGUANINE RIBOSIDE;6-CHLOROGUANOSINE;6-chloro-9-beta-D-ribofuranosyl-9H-purin-2-amine
• CAS NO: 2004-07-1
• Molecular Formula: C₁₀H₁₂ClN₅O₄
• Molecular Weight: 301.69
• EINECS: 217-905-3
• Product Categories: Miscellaneous Biochemicals;Heterocyclic Compounds;Biochemistry;Nucleosides and their analogs;Nucleosides, Nucleotides & Related Reagents;Bases & Related Reagents;Nucleotides;Aromatics
• Mol File: 2004-07-1.mol
• Article Data: 17

Chemical Properties

• Melting Point: 165-167 °C (dec.)(lit.)
• Boiling Point: 729.9 °C at 760 mmHg
• Flash Point: 395.2 °C
• Appearance: White to Off-white/Powder
• Density: 1.8359 (rough estimate)
• Vapor Pressure: 2.3E-22mmHg at 25°C
• Refractive Index: -38 ° (C=0.1, H2O)
• Storage Temp.: −20°C
• Solubility: DMSO, Methanol
• PKA: 13.05±0.70(Predicted)
• CAS DataBase Reference: 2-Amino-6-chloropurine-9-riboside(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-6-chloropurine-9-riboside(2004-07-1)
• EPA Substance Registry System: 2-Amino-6-chloropurine-9-riboside(2004-07-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• Hazardous Substances Data: 2004-07-1(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Crystalline Solid

Uses

6-Substituted purines; a novel class of inhibitors of endogenous protein degradation

InChI:InChI=1/C10H12ClN5O4/c11-7-4-8(15-10(12)14-7)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)

Upstream product

• 108321-99-9 α,β-D-ribofuranose-5-phophate disodium salt 
• 10310-21-1 2-Amino-6-chloropurin 
• 58-96-8 uridine 
• 28708-32-9 1,2,3,5-tetra-O-acetyl-D-ribofuranose 
• 19083-18-2 6-Chloro-2-fluoro-9-(β-D-ribofuranosyl)purine 
• 13276-52-3 2,6-dichloropurine riboside 
• 13035-61-5 1,2,3,5-tetraacetylribose 
• 5451-40-1 2,6-dichloro-7H-purine 
• 50-69-1 D-ribose 
• 81100-62-1 7-methylguanosine hydroiodide 
• 6979-94-8 2',3',5'-tri-O-acetyl-guanosine 
• 118-00-3 G 
• 67-56-1 methanol 
• 3387-63-1 2-amino-6-chloro-9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)purine 

Downstream Products

• 102830-41-1 O⁶-(2-hydroxy-2-phenylethyl)guanosine 
• 102830-40-0 O⁶-(2-hydroxy-2-phenylethyl)guanosine 
• 102830-38-6 O⁶-(2-hydroxy-1-phenylethyl)guanosine 
• 102830-39-7 O⁶-(2-hydroxy-12-phenylethyl)guanosine 
• 98383-43-8 N₆-(2,2-diphenylethyl)-2-aminoadenosine 
• 120524-29-0 (2R,3R,4S,5R)-2-[2-Amino-6-((R)-1-methyl-2-phenyl-ethylamino)-purin-9-yl]-5-hydroxymethyl-tetrahydro-furan-3,4-diol 
• 78907-22-9 O⁶-(p-methoxybenzyl)guanosine 
• 29411-74-3 6-selenoguanosine 
• 122970-35-8 2-amino-6-chloro-9-(2,3-dideoxy-β-D-glycero-pentofuranosyl)-9H-purine 
• 132194-22-0 2-amino-6-bromo-9-(2,3-dideoxy-β-D-glycero-pentofuranosyl)-9H-purine 
• 26783-37-9 2-amino-N⁶-(2-methyl-benzyl)-adenosine 
• 26783-34-6 2-amino-N⁶-(2-phenyl-propyl)-adenosine 
• 26775-40-6 2-amino-N⁶-(1-phenyl-ethyl)-adenosine 
• 26783-32-4 2-amino-6-(benzylamino)-9-(β-D-ribofuranosyl)purine 

Relevant articles and documents

Reaction of O6-methylguanosine with nitrite in the presence of carboxylic acid: Synthesis of the purin-2-yl carboxylate

O6-Methylguanosine derivative was treated with sodium nitrite or isoamylnitrite in the presence of carboxylic acid to give the purin-2-yl carboxylate, an unusual product bearing a carboxylic group at the 2-position of the purine moiety.

Intermediate for synthesizing 2-chloroadenosine, synthesis process of intermediate and synthesis process of 2-chloroadenosine

The invention relates to the technical field of organic synthesis, in particular to an intermediate for synthesizing 2-chloroadenosine, a synthesis process of the intermediate and a synthesis processof the 2-chloroadenosine. The synthesis process of the intermediate for synthesizing the 2-chloroadenosine comprises the following step: carrying out condensation reaction on 2,6-dichloropurine and tetraacetylribose under the catalytic action of 4-dimethylaminopyridine to form 2,3,5-4-triacetyl-2,6-dichloropurine riboside. The synthesis process is simple to operate, low in catalyst dosage, low incost, low in pollution and easy to industrially implement, and the yield and purity of the synthesized 2-chloroadenosine are higher.

Synthesis of novel 6-substituted amino-9-(β-D-ribofuranosyl)purine analogs and their bioactivities on human epithelial cancer cells

New nucleoside derivatives with nitrogen substitution at the C-6 position were prepared and screened initially for their in vitro anticancer bioactivity against human epithelial cancer cells (liver Huh7, colon HCT116, breast MCF7) by the NCI-sulforhodamine B assay. N6-(4-trifluoromethylphenyl)piperazine analog (27) exhibited promising cytotoxic activity. The compound 27 was more cytotoxic (IC50 = 1–4 μM) than 5-FU, fludarabine on Huh7, HCT116 and MCF7 cell lines. The most potent nucleosides (11, 13, 16, 18, 19, 21, 27, 28) were further screened for their cytotoxicity in hepatocellular cancer cell lines. The compound 27 demonstrated the highest cytotoxic activity against Huh7, Mahlavu and FOCUS cells (IC50 = 1, 3 and 1 μM respectively). Physicochemical properties, drug-likeness, and drug score profiles of the molecules showed that they are estimated to be orally bioavailable. The results pointed that the novel derivatives would be potential drug candidates.

CHEMO-ENZYMATIC PREPARATION METHOD FOR PURINE NUCLEOSIDES AND THEIR DEAZA- AND AZA- ANALOGUES

The present invention relates to a new, chemo-enzymatic preparation method of purine nucleosides and their deaza- and aza analogues of general formula I or pharmaceutically acceptable esters or salts thereof (I) wherein X, Y, Z and V independently from each other represent a nitrogen or carbon atom, W represents a nitrogen atom, -CH, -CF or –C-NH2, R1 represents hydrogen, fluorine (ribo/arabino), -OH (ribo/arabino) or -NH2 (ribo), R 2 represents -OH, -NH 2 or hydrogen,and Sub 2 and Sub 6 represent hydrogen, chlorine, fluorine, bromine or -NH 2, wherein at least one of Sub 2 and Sub 6 is -NH2.