2-Chloro-N6-cyclopentyladenosine

Base Information

• Chemical Name: 2-Chloro-N6-cyclopentyladenosine
• CAS No.: 37739-05-2
• Molecular Formula: C₁₅H₂₀ClN₅O₄
• Molecular Weight: 369.808
• Hs Code.: 29349990
• UNII: JX2F2W6WSP
• DSSTox Substance ID: DTXSID00958774
• Nikkaji Number: J373.039E
• Wikipedia: CCPA_(biochemistry)
• Wikidata: Q5009685
• Pharos Ligand ID: CQ7111K9ZLCD
• ChEMBL ID: CHEMBL284969
• Mol file: 37739-05-2.mol

Synonyms:2-CCPA;2-chloro-N(6)cyclopentyladenosine;CCPA-2;CCPA-2-chloro-N(6)-cyclopentyladenosine;CCPA-2-Cl-N-CPA

Chemical Property of 2-Chloro-N6-cyclopentyladenosine

Chemical Property:

• Appearance/Colour: off-white to light yellow solid
• Vapor Pressure: 4.26E-16mmHg at 25°C
• Refractive Index: 1.824
• Boiling Point: 617.3 °C at 760 mmHg
• PKA: 13.06±0.70(Predicted)
• Flash Point: 327.1 °C
• PSA: 125.55000
• Density: 1.87 g/cm³
• LogP: 0.51870
• Storage Temp.: 2-8°C
• Solubility.: H2O: 1.7 mg/mL, insoluble
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 369.1203818
• Heavy Atom Count: 25
• Complexity: 471

Purity/Quality:

97% ^*data from raw suppliers

2-Chloro-N6-cyclopentyl Adenosine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CCC(C1)NC2=C3C(=NC(=N2)Cl)N(C=N3)C4C(C(C(O4)CO)O)O
• Isomeric SMILES: C1CCC(C1)NC2=C3C(=NC(=N2)Cl)N(C=N3)[C@H]4[C@@H]([C@@H]([C@H](O4)CO)O)O
• Uses: Adenosine receptors are for treating central nervous system (CNS) disorders. Adenosine A1 receptor agonists include e.g. CCPA, 8-cyclopentyl-1,3-dipropylxanthine, R-phenylisopropyl adenosine. A2A rec eptor agonists include e.g. regadenoson (Lexiscan), apadenoson, binodenoson. 2-Chloro-N6-cyclopentyl Adenosine is a selective adenosine receptor agonist (1,2). It inhibits angiotensin II induced cardiomyocyte hypertrophy via the calcineurin signaling pathway (2). 2-Chloro-N6-cyclopentyladenosine (CCPA) may be used as an A1 adenosine receptor agonist with high selectivity. CCPA is often used with other adenosine receptor agonists and antagonist to resolve A(1), A(2A) and A(3) receptor functions. These include DPCPX (A(1) receptor antagonist), 4-(2-[7-amino-2-(2-furyl)[1,2,4]triazolo[2,3-α][1,3,5]triazin-5-ylamino]ethyl)phenol (A(2A) receptor antagonist), and 4-[2-[[6-amino-9-(N-ethyl-β-D-ribofuranuronamidosyl)-9H-purin-2-yl]amino]ethyl]benzenepropanoic acid hydrochloride (A(2A) receptor agonist), and Cl-IB-MECA, (A(3)) receptor agonist).

Technology Process of 2-Chloro-N6-cyclopentyladenosine

There total 8 articles about 2-Chloro-N6-cyclopentyladenosine 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: 80.0%

(2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(2,6-dichloro-9H-purin-9-yl)tetrahydro-3-furanyl acetate (3056-18-6) + Cyclopentamine (1003-03-8) → 2-chloro-N6-cyclopentyladenosine (37739-05-2)

Guidance literature:

(2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(2,6-dichloro-9H-purin-9-yl)tetrahydro-3-furanyl acetate; Cyclopentamine; at 20 ℃; for 4h;

With ammonia; In methanol; at 20 ℃; for 24h; Further stages.;

DOI:10.1021/jm9911231

Reference yield:

Cyclopentamine (1003-03-8) + 2,6-dichloropurine riboside (13276-52-3) → 2-chloro-N6-cyclopentyladenosine (37739-05-2)

Guidance literature:

With triethylamine; In ethanol; at 60 ℃;

Reference yield:

C16H22Cl2N4O6 + Cyclopentamine (1003-03-8) → 2-chloro-N6-cyclopentyladenosine (37739-05-2)

Guidance literature:

In ethanol; for 15h; Reflux;

upstream raw materials:

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

Cyclopentamine

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-chloro-6-cyclopentylamino-purin-9-yl)-tetrahydro-furan-3-yl ester

2',3',5'-tri-O-acetyl-O₆-(benzotriazol-1-yl)guanosine

Downstream raw materials:

N-cyclopentyladenosine