Vesnarinone

Base Information

• Chemical Name: Vesnarinone
• CAS No.: 81840-15-5
• Molecular Formula: C22H25N3O4
• Molecular Weight: 395.458
• UNII: 5COW40EV8M
• DSSTox Substance ID: DTXSID80231411
• Nikkaji Number: J22.952K
• Wikipedia: Vesnarinone
• Wikidata: Q7923264
• NCI Thesaurus Code: C1415
• Pharos Ligand ID: CLZLYM2US8G1
• Metabolomics Workbench ID: 49724
• ChEMBL ID: CHEMBL17423
• Mol file: 81840-15-5.mol

Synonyms:3,4-dihydro-6-(4-(3,4-dimethoxybenzoyl)-1-piperazinyl)-2-1H-quinolinone;OPC 8212;OPC-8212;vesnarinone

Chemical Property of Vesnarinone

Chemical Property:

• Vapor Pressure: 2.96E-18mmHg at 25°C
• Melting Point: 238.1-239.5° (Tominaga); mp 238.1-239.8° (Shimizu)
• Refractive Index: 1.6500 (estimate)
• Boiling Point: 678.3°C at 760 mmHg
• PKA: 2.86(at 25℃)
• Flash Point: 364°C
• PSA: 71.11000
• Density: 1.246g/cm³
• LogP: 2.69180
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 395.18450629
• Heavy Atom Count: 29
• Complexity: 593

Purity/Quality:

98%min ^*data from raw suppliers

Vesnarinone(OPC8212) >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C(=O)N2CCN(CC2)C3=CC4=C(C=C3)NC(=O)CC4)OC
• Recent ClinicalTrials: A Phase I Study of Three Doses of OPC-8212 (Vesnarinone) in HIV-Infected Persons With CD4+ Cell Number > 300 Cells/mm3
• Description: Vesnarinone is a new orally-active positive inotropic agent introduced for the treatment of congestive heart failure. It exerts a positive inotropic effect on the heart and has a peripheral vasodilatory effect. Vesnarinone is claimed not to affect heart rate or aggravate arrhythmia. Vesnarinone is an inhibitor of phosphodiesterase 3 (PDE3; IC50s = 10.7 and 13.2 μM for PDE3A and PDE3B, respectively). It also inhibits ether-a-go-go-related gene 1 (ERG1) channels (IC50 = 1.1 μM in HEK293T cells expressing human ERG1). Vesnarinone (3-300 μM) increases contractile tension in isolated ventricular muscles of dog, cat, rabbit, and guinea pig in a dose-dependent manner. Oral and i.v. administration of vesnarinone increases right ventricular pressure with no effect on heart rate in dog models of tricuspid insufficiency- and pulmonary stenosis-induced congestive heart failure. It also increases contractility and coronary flow while decreasing heart rate in a guinea pig model of aortic stenosis-induced congestive heart failure. Formulations containing vesnarinone have been used for the treatment of congestive heart failure.
• Uses: Cardiotonic.

Technology Process of Vesnarinone

There total 15 articles about Vesnarinone 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%

carbon monoxide (201230-82-2) + 4-Bromoveratrole (2859-78-1) + 6-(1-piperazinyl)-3,4-dihydro-2(1H)-quinolinone (87154-95-8) → vesnarinone (81840-15-5)

Guidance literature:

With potassium carbonate; bis[2-(diphenylphosphino)phenyl] ether; In 1,4-dioxane; at 120 ℃; under 7500.75 Torr;

DOI:10.1002/ejoc.201403054

Reference yield: 74.0%

6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydroquinolin-2(1H)-one (400620-72-6) + 1-(3,4-dimethoxybenzoyl)piperazine → vesnarinone (81840-15-5)

Guidance literature:

With copper diacetate; boric acid; In acetonitrile; at 80 ℃; for 24h; Molecular sieve; Sealed tube;

DOI:10.1002/cjoc.202000212

Reference yield: 70.0%

6-(1-piperazinyl)-3,4-dihydrocarbostyril hydrobromide (86813-31-2) + 3,4-dimethoxybenzoic acid chloride (3535-37-3) → vesnarinone (81840-15-5)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; for 1h; Ambient temperature;

DOI:10.1248/cpb.32.2100

upstream raw materials:

6-(1-piperazinyl)-3,4-dihydrocarbostyril hydrobromide

3,4-dimethoxybenzoic acid chloride

6-amino-3,4-dihydro-1H-quinolin-2-one

bis(2-bromoethyl)amine hydrobromide

Downstream raw materials:

1-(2-propynyl)-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril

Veratric acid

6-(1-piperazinyl)-3,4-dihydro-2(1H)-quinolinone

ethyl veratrate

Refernces

• 1、 See, Yi Yang,Dang, Tuan Thanh,Chen, Anqi,Seayad, Abdul Majeed. "Concise Synthesis of Vesnarinone and Its Analogues by Using Pd-Catalyzed C-N Bond-Forming Reactions". . p. 7405 - 7412. Retrieved 2016/02/19.
• 2、 -. "Piperazinylcarbostyril compounds". . . Retrieved 2008/06/13.