Sumanirole

Base Information

• Chemical Name: Sumanirole
• CAS No.: 179386-43-7
• Molecular Formula: C11H13 N3 O
• Molecular Weight: 203.2404
• Hs Code.: 2933990090
• UNII: 3E93IV1U45
• DSSTox Substance ID: DTXSID00870144
• Nikkaji Number: J813.608D
• Wikipedia: Sumanirole
• Wikidata: Q7636953
• NCI Thesaurus Code: C76651
• Pharos Ligand ID: RLS7T4AC9CKY
• Metabolomics Workbench ID: 149799
• ChEMBL ID: CHEMBL419792
• Mol file: 179386-43-7.mol

Synonyms:5,6-dihydro-5-(methylamino)-4H-imidazo(4,5,1ij)-quinolin-2(1H)-one (Z)-2-butenedioate;PNU-95666;Sumanirole;U 95666E;U-95666E

Chemical Property of Sumanirole

Chemical Property:

• PSA: 50.08000
• Density: 1.323g/cm³
• LogP: 1.27690
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 203.105862047
• Heavy Atom Count: 15
• Complexity: 281

Purity/Quality:

>98 % ^*data from raw suppliers

Sumanirole maleate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC1CC2=C3C(=CC=C2)NC(=O)N3C1
• Isomeric SMILES: CN[C@@H]1CC2=C3C(=CC=C2)NC(=O)N3C1
• Recent ClinicalTrials: Open Label Sumanirole Study of Safety, Tolerability, and Therapeutic Response In Patients With Parkinson's Disease
• Uses: Sumanirole is a high affinity D2 receptor agonist (EC50 values are between 17 and 75 nM in cell-based assays). Sumanirole displays >200-fold selectivity for the D2 receptor against other dopamine rece ptor subtypes (Ki values are 9.0, 1940, >2190 and >7140 for D2, D3, D4 and D1 receptors respectively). Sumanirole exhibits antiParkinsonian activity similar to Ropinirole (R641000).

Technology Process of Sumanirole

There total 29 articles about Sumanirole 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: 92.0%

tert-butyl (R)-methyl(2-oxo-1,2,5,6-tetrahydro-4H-imidazo[4,5,1-ij]quinolin-5-yl)carbamate (186320-51-4) → (R)-5,6-Dihydro-5-(methylamino)-4H-imidazo[4,5,1-ij]-quinolin-2(1H)-one (179386-43-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 12h; Inert atmosphere;

DOI:10.1016/j.tetasy.2014.06.018

Reference yield: 67.0%

C19H19N3O → (R)-5,6-Dihydro-5-(methylamino)-4H-imidazo[4,5,1-ij]-quinolin-2(1H)-one (179386-43-7)

Guidance literature:

With N,N'-Dimethylurea; tris(pyrrolidino)phosphine oxide; lithium bromide; In tetrahydrofuran; at 20 ℃; Electrochemical reaction;

DOI:10.1126/science.aav5606

Reference yield:

(R)-5-(Benzyl-methyl-amino)-5,6-dihydro-1H,4H-imidazo[4,5,1-ij]quinolin-2-one (185943-25-3) → (R)-5,6-Dihydro-5-(methylamino)-4H-imidazo[4,5,1-ij]-quinolin-2(1H)-one (179386-43-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 18h; under 2585.7 Torr;

DOI:10.1021/jm960360q

upstream raw materials:

(R)-5-(Benzyl-methyl-amino)-5,6-dihydro-1H,4H-imidazo[4,5,1-ij]quinolin-2-one

((R)-1-Methoxy-2-oxo-1,2,5,6-tetrahydro-4H-imidazo[4,5,1-ij]quinolin-5-yl)-methyl-carbamic acid benzyl ester

(R)-methyl-(1,2,3,4-tetrahydro-3-quinolinyl)carbamic acid, phenylmethyl ester

((R)-1-Methoxycarbamoyl-1,2,3,4-tetrahydro-quinolin-3-yl)-methyl-carbamic acid benzyl ester