Tonapofylline

Base Information

• Chemical Name: Tonapofylline
• CAS No.: 340021-17-2
• Molecular Formula: C22H32N4O4
• Molecular Weight: 416.5139
• UNII: 83VNU4U44T
• DSSTox Substance ID: DTXSID30187611
• Wikidata: Q27089006
• NCI Thesaurus Code: C96194
• Pharos Ligand ID: 6LPJ4DRUZQDF,6LPR22A65F1S
• Metabolomics Workbench ID: 153535
• ChEMBL ID: CHEMBL414157,CHEMBL386974
• Mol file: 340021-17-2.mol

Synonyms:3-(4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo(2.2.2)oct-1-yl)propionic acid;BG 9928;BG-9928;BG9928;BIO 4683;BIO 5770;BIO 7505;BIO 8170;BIO 9002;BIO-4683;BIO-5770;BIO-7505;BIO-8170;BIO-9002;BIO4683;BIO5770;BIO7505;BIO8170;BIO9002;tonapofylline

Chemical Property of Tonapofylline

Chemical Property:

• Vapor Pressure: 1.32E-18mmHg at 25°C
• Boiling Point: 665.3°C at 760 mmHg
• PKA: 4.81±0.10(Predicted)
• Flash Point: 356.2°C
• PSA: 109.98000
• Density: 1.273g/cm³
• LogP: 3.16310
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 416.24235551
• Heavy Atom Count: 30
• Complexity: 687

Purity/Quality:

≥98% ^*data from raw suppliers

Tonapofylline ≥98.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCN1C2=C(C(=O)N(C1=O)CCC)NC(=N2)C34CCC(CC3)(CC4)CCC(=O)O
• Recent ClinicalTrials: Oral Tonapofylline (BG9928) in Patients With Heart Failure and Renal Insufficiency
• Recent EU Clinical Trials: A Randomised, Double-Blind, Placebo-Controlled, Parallel-Group Study to Assess the Safety and Tolerability of Oral Tonapofylline in Patients with Heart Failure and Renal Insufficiency

Technology Process of Tonapofylline

There total 29 articles about Tonapofylline 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: 100.0%

(E)-3-(4-(2,6-dioxo-1,3-dipropyl-2,3,6,9-tetrahydro-1H-purin-8-yl)bicyclo[2.2.2]octan-1-yl)acrylic acid → 3-(4-(2,6-dioxo-1,3-dipropyl-2,3,6,9-tetrahydro-1H-purin-8-yl)bicyclo[2.2.2]octan-1-yl)propanoic acid (340021-17-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 2h;

DOI:10.1021/acs.jmedchem.0c02067

Reference yield: 74.0%

(E)-3-[4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-acrylic acid (340021-16-1) → 3-[4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-propionic acid (340021-17-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 2h;

DOI:10.1021/jm0605381

Reference yield:

C22H33N5O3 → 3-(4-(2,6-dioxo-1,3-dipropyl-2,3,6,9-tetrahydro-1H-purin-8-yl)bicyclo[2.2.2]octan-1-yl)propanoic acid (340021-17-2)

Guidance literature:

C₂₂H₃₃N₅O₃; With water; potassium hydroxide; at 120 ℃; for 18h; Sealed vial;

With hydrogenchloride; In water; at 20 ℃; for 1h; pH=2;

upstream raw materials:

(E)-3-[4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-acrylic acid

3-[4-(6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydropyrimidin-5-ylcarbamoyl)bicyclo[2.2.2]oct-1-yl]propionic acid methyl ester

bicyclo[2.2.2]octane-1,4-dicarboxylic acid monomethyl ester

methyl 4-(carbonochloridoyl)bicyclo[2.2.2]octane-1-carboxylate

Refernces

• 1、 -. "NOVEL SYNTHETIC METHODS". . . Retrieved 2011/06/19.
• 2、 -. "Methods of treating pulmonary disease". . . Retrieved 2008/06/13.