2-Chloroadenosine

Base Information

• Chemical Name: 2-Chloroadenosine
• CAS No.: 146-77-0
• Molecular Formula: C10H12ClN5O4
• Molecular Weight: 301.689
• Hs Code.: 29349990
• European Community (EC) Number: 205-678-3,630-491-2
• UNII: 7W7ZUG45G8
• DSSTox Substance ID: DTXSID301017134
• Nikkaji Number: J86.653I
• Wikidata: Q27071883
• Pharos Ligand ID: B7F3YCBGC26Y
• Metabolomics Workbench ID: 130033
• ChEMBL ID: CHEMBL285819
• Mol file: 146-77-0.mol

Synonyms:2 Chloroadenosine;2-Chloroadenosine

Chemical Property of 2-Chloroadenosine

Chemical Property:

• Appearance/Colour: white to off-white crystalline solid
• Melting Point: 162 °C
• Refractive Index: -50 ° (C=0.1, H2O)
• Boiling Point: 591.8 °C at 760 mmHg
• PKA: 13.05±0.70(Predicted)
• Flash Point: 311.7 °C
• PSA: 139.54000
• Density: 2.19 g/cm³
• LogP: -0.74540
• Storage Temp.: Store at +4°C
• Solubility.: H2O: 10 mg/mL, clear, colorless
• Water Solubility.: Soluble in water.
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 301.0577816
• Heavy Atom Count: 20
• Complexity: 367

Purity/Quality:

99% ^*data from raw suppliers

2-Chloroadenosine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

Useful:

• Canonical SMILES: C1=NC2=C(N=C(N=C2N1C3C(C(C(O3)CO)O)O)Cl)N
• Isomeric SMILES: C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)Cl)N
• Uses: 2-Chloroadenosine is an adenosine analogue that is not hydrolyzed by adenosine deaminase. 2-Chloroadenosine increases the rate of dopa production in intact pheochromocytoma cells, it increases the content of cAMP in the cells, and it causes a stable activation of tyrosine hydroxylase, as measured in vitro. The action of 2-Chloroadenosine is not dependent upon extracellular Ca2+. In other experiments, we have found that 2-chloroadenosine increases the activity of adenylate cyclase in membrane fractions prepared from the pheochromocytoma. These data provide support for the hypothesis that 2-Chloroadenosine causes a cAMP-mediated phosphorylation of tyrosine hydroxylase in pheochromocytoma cells. Chromaffin cells and adrenergic neurons store and release adenine nuc1eotides together with catecho1amines. The adenosine formed by the hydrolysis of these nucleotides may be involved in the. physiological regulation of adenylate cyclase activity and of tyrosine hydroxylase activity. To date , however, we have no evidence for such a role of adenosine in normal chromaffin cells or in adrenergic neurons. A selective A1-adenosine receptor agonist. Induces apoptosis Selective A1 adenosine receptor agonist. Since 2-chloroadenosine is not deaminated by adenosine deaminase and is less rapidly taken up by the brain than adenosine, 2-chloroadenosine led to more marked increase in CBF than adenosine. 2-Chloroadenosine is used as a selective A1-adenosine receptor agonist, and also Induces apoptosis.

Technology Process of 2-Chloroadenosine

There total 29 articles about 2-Chloroadenosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

2',3',5'-tri-O-acetyl-2-chloroadenosine (79999-39-6,24638-99-1) → 2-Chloroadenosine (146-77-0)

Guidance literature:

With methanol; sodium methylate; for 1h; Reflux;

Reference yield: 85.0%

2-chloroadenine (1839-18-5) + uridine (58-96-8) → 2-Chloroadenosine (146-77-0)

Guidance literature:

With hydrogenchloride; potassium dihydrogenphosphate; potassium hydroxide; In water; dimethyl sulfoxide; at 58 - 61 ℃; for 4h; pH=7.1-7.2; Enzymatic reaction;

Reference yield: 75.0%

(2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(2,6-dichloro-9H-purin-9-yl)tetrahydro-3-furanyl acetate (3056-18-6) → 2-Chloroadenosine (146-77-0)

Guidance literature:

With ethanol; ammonia; at 20 ℃;

DOI:10.1021/acs.jmedchem.9b01611

upstream raw materials:

2-chloro-6-methoxy-purine riboside

2,8-dichloro-adenosine

(2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(2,6-dichloro-9H-purin-9-yl)tetrahydro-3-furanyl acetate

2,3,5-tri-O-acetyl-α-D-ribofuranosyl chloride

Downstream raw materials:

2-Methoxyadenosine

2-(methylthio)adenosine

2-dimethylamino-adenosine

2-(methylamino)adenosine

Refernces

• 1、 Weber,Sampino,Dunphy,Burinsky,Williams,Motto. "Characterization of cladribine and its related compounds by high- performance liquid chromatography/mass spectrometry". . p. 525 - 531. Retrieved 1994.
• 2、 Brown,Weliky. "-". . p. 125. Retrieved 1958.
• 3、 Kaspar, Felix,Giessmann, Robert T.,Hellendahl, Katja F.,Neubauer, Peter,Wagner, Anke,Gimpel, Matthias. "General Principles for Yield Optimization of Nucleoside Phosphorylase-Catalyzed Transglycosylations". . p. 1428 - 1432. Retrieved 2020/02/05.
• 4、 Zhang, Min,Fan, Shiyong,Zhou, Xinbo,Xie, Fei,Li, Song,Zhong, Wu. "Design, synthesis and biological evaluation of 2-hydrazinyladenosine derivatives as A2A adenosine receptor ligands". . p. 310 - 324. Retrieved 2019/07/02.