N6-Phenethyladenosine;N6-Phenylethyladenosine

Base Information

• Chemical Name: N6-Phenethyladenosine;N6-Phenylethyladenosine
• CAS No.: 20125-39-7
• Molecular Formula: C18H21N5O4
• Molecular Weight: 371.396
• NSC Number: 281310
• DSSTox Substance ID: DTXSID00875053
• Mol file: 20125-39-7.mol

Synonyms:SMR000326857;N6-2-Phenylethyladenosine;NSC281310;N6-Phenethyladenosine;N6-Phenylethyladenosine;MLS000859998;MLS002153479;DTXSID00875053;HMS2234J13;ADENOSINE,6N-2-PHENYLETHYL;NSC-281310;J-013033

Chemical Property of N6-Phenethyladenosine;N6-Phenylethyladenosine

Chemical Property:

• Vapor Pressure: 5.72E-22mmHg at 25°C
• Melting Point: 167-168 °C
• Boiling Point: 723.5°Cat760mmHg
• PKA: 13.12±0.70(Predicted)
• Flash Point: 391.3°C
• PSA: 125.55000
• Density: 1.57g/cm³
• LogP: 0.16540
• Storage Temp.: 2-8°C
• Solubility.: 0.1 M NaOH: soluble
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 371.15935417
• Heavy Atom Count: 27
• Complexity: 481

Purity/Quality:

98% ^*data from raw suppliers

N6-(2-Phenylethyl)adenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CCNC2=C3C(=NC=N2)N(C=N3)C4C(C(C(O4)CO)O)O
• Uses: N6-(2-Phenylethyl)adenosine is an adenosine analogs that possesses anti-proliferative activity on bladder cancer cells. Potent ligands at the human A3 adenosine receptor.

Technology Process of N6-Phenethyladenosine;N6-Phenylethyladenosine

There total 9 articles about N6-Phenethyladenosine;N6-Phenylethyladenosine 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: 94.0%

(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-bromo-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (74465-47-7) + phenethylamine (64-04-0) → N6-(2-phenylethyl)adenosine (20125-39-7)

Guidance literature:

(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-bromo-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate; phenethylamine; In 1,2-dimethoxyethane; at 20 ℃; for 4h;

With ammonia; In methanol; at 20 ℃;

Reference yield: 91.0%

6-Chloropurine riboside (2004-06-0) + phenethylamine (64-04-0) → N6-(2-phenylethyl)adenosine (20125-39-7)

Guidance literature:

With triethylamine; In butan-1-ol; Heating;

Reference yield: 82.0%

→ N6-(2-phenylethyl)adenosine (20125-39-7)

Guidance literature:

upstream raw materials:

6-Chloropurine riboside

phenethylamine

pyrographite

inosine

Downstream raw materials:

((3aR,4R,6R,6aR)-2,2-dimethyl-6-(6-(phenethylamino)-9H-purin-9-yl)-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

Refernces

• 1、 Goswami, Manibarsha,Wilke, Kaelyn E.,Carlson, Erin E.. "Rational Design of Selective Adenine-Based Scaffolds for Inactivation of Bacterial Histidine Kinases". supporting information. p. 8170 - 8182. Retrieved 2017/10/18.
• 2、 Bhattarai, Sanjay,Freundlieb, Marianne,Pippel, Jan,Meyer, Anne,Abdelrahman, Aliaa,Fiene, Amelie,Lee, Sang-Yong,Zimmermann, Herbert,Yegutkin, Gennady G.,Str?ter, Norbert,El-Tayeb, Ali,Müller, Christa E.. "α,β-Methylene-ADP (AOPCP) Derivatives and Analogues: Development of Potent and Selective ecto-5′-Nucleotidase (CD73) Inhibitors". supporting information. p. 6248 - 6263. Retrieved 2015/08/24.