Verlukast

Base Information

• Chemical Name: Verlukast
• CAS No.: 115104-28-4
• Deprecated CAS: 135028-15-8,129954-35-4,120663-36-7,120443-14-3
• Molecular Formula: C₂₆H₂₇ClN₂O₃S₂
• Molecular Weight: 515.097
• UNII: 76LB1G2X6V
• ChEMBL ID: CHEMBL15177
• DSSTox Substance ID: DTXSID5048390
• Metabolomics Workbench ID: 70474
• NCI Thesaurus Code: C96714
• Nikkaji Number: J364.035C
• Pharos Ligand ID: TYKB6ZMF5QCW
• Wikidata: Q27107275
• Mol file: 115104-28-4.mol

Synonyms:(3-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)((3-dimethylamino-3-oxopropyl)thio)methyl)thiopropanoic acid;L 660,711;L 660711;L-660711;MK 0571;MK 0679;MK 571;MK-0571;MK-0679;MK-571;MK-679;MK571 cpd;verlukast;verlukast, (R-(E))-isomer

Chemical Property of Verlukast

Chemical Property:

• Vapor Pressure: 2.72E-21mmHg at 25°C
• Melting Point: 65-70°C
• Boiling Point: 712.3°Cat760mmHg
• PKA: 4.27±0.10(Predicted)
• Flash Point: 384.6°C
• PSA: 121.10000
• Density: 1.327g/cm³
• LogP: 6.47660
• Storage Temp.: Store at -20°C
• Solubility.: Soluble in DMSO (up to 50 mg/ml).
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 514.1151628
• Heavy Atom Count: 34
• Complexity: 693

Purity/Quality:

97% ^*data from raw suppliers

MK 571 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C(=O)CCSC(C1=CC=CC(=C1)C=CC2=NC3=C(C=CC(=C3)Cl)C=C2)SCCC(=O)O
• Isomeric SMILES: CN(C)C(=O)CCSC(C1=CC=CC(=C1)/C=C/C2=NC3=C(C=CC(=C3)Cl)C=C2)SCCC(=O)O
• Description: MK-571 is a selective, orally active CysLT1 receptor antagonist. It blocks the binding of LTD4, but not LTC4, to human and guinea pig lung membranes with Ki values of 0.22 nM and 2.1 nM, respectively, which is indicative of CysLT1 receptor-mediated activity in these preparations. MK-571 effectively blocks LTD4 activation of recombinant human and murine CysLT1 receptors but is ineffective at blocking LTC4 or LTD4 activation of the recombinant human or murine CysLT2 receptors.
• Uses: A receptor antagonist for the treatment of respiratory diseases. Cysteinyl leukotriene receptor antagonist MK-571 alters bronchoalveolar lavage fluid proteome in asthma. A receptor antagonist for the treatment of respiratory diseases. Cysteinyl leukotriene receptor antagonist MK-571 alters bronchoalveolar lavage fluid proteome in asthma

Technology Process of Verlukast

There total 22 articles about Verlukast 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: 50.0%

3-[{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-(2-dimethylcarbamoyl-ethylsulfanyl)-methylsulfanyl]-propionic acid methyl ester (115104-27-3,115104-52-4,115104-56-8,120443-15-4,120443-18-7,120663-37-8,124601-75-8) → (+)-L-660,711 (115104-28-4,120443-16-5,120443-17-6,121702-00-9,135028-15-8,143899-88-1)

Guidance literature:

With lithium hydroxide; water; In 1,2-dimethoxyethane; for 3h; Ambient temperature;

Reference yield:

3-[{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-(2-dimethylcarbamoyl-ethylsulfanyl)-methylsulfanyl]-propionic acid methyl ester (115104-27-3,115104-52-4,115104-56-8,120443-15-4,120443-18-7,120663-37-8,124601-75-8) → (-)-L-660,711 (115104-28-4,120443-16-5,120443-17-6,121702-00-9,135028-15-8,143899-88-1)

Guidance literature:

With lithium hydroxide; water; In 1,2-dimethoxyethane; for 3h; Ambient temperature;

Reference yield:

2-methyl-7-chloroquinoline (4965-33-7) → (+)-L-660,711 (115104-28-4,120443-16-5,120443-17-6,121702-00-9,135028-15-8,143899-88-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 120 g / N-bromosuccinimide, benzoyl peroxide / CCl₄ / 48 h / Heating; Irradiation

2: 170 g / acetonitrile / 60 °C

3: 96 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 0.5 h, 2.) room temperature, 2 h

4: 50 percent / LiOH, water / 1,2-dimethoxy-ethane / 3 h / Ambient temperature

With lithium hydroxide; N-Bromosuccinimide; n-butyllithium; Perbenzoic acid; water; In tetrahydrofuran; tetrachloromethane; 1,2-dimethoxyethane; hexane; acetonitrile;

upstream raw materials:

3-[{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-(2-dimethylcarbamoyl-ethylsulfanyl)-methylsulfanyl]-propionic acid methyl ester

2-methyl-7-chloroquinoline

Isophthalaldehyde

3-(hydroxymethyl)benzaldehyde