Capadenoson

Base Information

• Chemical Name: Capadenoson
• CAS No.: 544417-40-5
• Molecular Formula: C₂₅H₁₈ClN₅O₂S₂
• Molecular Weight: 520.035
• European Community (EC) Number: 695-646-9
• UNII: O519NVW73R
• DSSTox Substance ID: DTXSID50969597
• Nikkaji Number: J2.940.437B
• Wikidata: Q27285331
• NCI Thesaurus Code: C87279
• Pharos Ligand ID: WLR8C27D2ZPV
• ChEMBL ID: CHEMBL3235279
• Mol file: 544417-40-5.mol

Synonyms:BAY-68-4986;capadenoson

Chemical Property of Capadenoson

Chemical Property:

• Boiling Point: 787.9±70.0 °C(Predicted)
• PKA: 13.98±0.10(Predicted)
• PSA: 182.38000
• Density: 1.51
• LogP: 6.09566
• Solubility.: Soluble in DMSO
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 8
• Exact Mass: 519.0590449
• Heavy Atom Count: 35
• Complexity: 774

Purity/Quality:

98%Min ^*data from raw suppliers

Capadenoson >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2=C(C(=NC(=C2C#N)SCC3=CSC(=N3)C4=CC=C(C=C4)Cl)N)C#N)OCCO
• Recent ClinicalTrials: Study to Investigate the Effect of the A1 Agonist Capadenoson on Ventricular HR in Patients With Persistent or Permanent Atrial Fibrillation.
• Recent EU Clinical Trials: Study to investigate the effect of the A1 agonist capadenoson on ventricular HR in patients with persistent or permanent atrial fibrillation by administration of capadenoson in a dose of 4 mg once daily for five days

Technology Process of Capadenoson

There total 5 articles about Capadenoson 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%

→ Capadenoson (544417-40-5)

Guidance literature:

Reference yield: 75.1%

4-chloromethyl-2-(4-chloro-phenyl)-thiazole (17969-22-1) + 2-[4-(2-hydroxyethoxy)benzylidene]malononitrile (112906-84-0) + Cyanothioacetamide (7357-70-2) → Capadenoson (544417-40-5)

Guidance literature:

2-[4-(2-hydroxyethoxy)benzylidene]malononitrile; Cyanothioacetamide; With triethylamine; In methanol; at 40 ℃; for 3h; Large scale;

4-chloromethyl-2-(4-chloro-phenyl)-thiazole; In methanol; at 5 - 30 ℃; Large scale;

Reference yield:

4-chloromethyl-2-(4-chloro-phenyl)-thiazole (17969-22-1) + 2-amino-4-[4-(2-hydroxyethoxy)phenyl]-6-sulfanylpyridine-3,5-dicarbonitrile (544417-72-3) → Capadenoson (544417-40-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 20 ℃;

upstream raw materials:

4-chloromethyl-2-(4-chloro-phenyl)-thiazole

2-amino-4-[4-(2-hydroxyethoxy)phenyl]-6-sulfanylpyridine-3,5-dicarbonitrile

4-chlorothiobenzamide

2-[4-(2-hydroxyethoxy)benzylidene]malononitrile

Downstream raw materials:

2-(4-(2-(((2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl)sulfanyl)-3,5-dicyano-6-(pyrrolidin-1-yl)pyridin-4-yl)phenoxy)ethyl N²,N⁶-bis(tert-butoxycarbonyl)-L-lysyl-L-alaninate

2-((2-(4-chlorophenyl)-1,3-thiazol-4-ylmethyl)sulfanyl)-4-(4-(2-hydroxyethoxy)phenyl)-6-(piperidin-1-yl)pyridine-3,5-dicarbonitrile

2-(((2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl)sulfanyl)-4-(4-(2-hydroxyethoxy)phenyl)-6-(methylamino)pyridine-3,5-dicarbonitrile

2-(azetidin-1-yl)-6-((2-(4-chlorophenyl)-1,3-thiazol-4-ylmethyl)sulfanyl)-4-(4-(2-hydroxyethoxy)phenyl)pyridine-3,5-dicarbonitrile

Refernces

• 1、 Meibom, Daniel,Albrecht-Küpper, Barbara,Diedrichs, Nicole,Hübsch, Walter,Kast, Raimund,Kr?mer, Thomas,Krenz, Ursula,Lerchen, Hans-Georg,Mittendorf, Joachim,Nell, Peter G.,Süssmeier, Frank,Vakalopoulos, Alexandros,Zimmermann, Katja. "Neladenoson Bialanate Hydrochloride: A Prodrug of a Partial Adenosine A1 Receptor Agonist for the Chronic Treatment of Heart Diseases". . p. 728 - 737. Retrieved 2017/05/26.
• 2、 -. "ALKYLAMINO-SUBSTITUTED DICYANOPYRIDINES AND THEIR AMINO ACID ESTER PRODRUGS". . . Retrieved 2010/08/08.