Roquinimex

Base Information

• Chemical Name: Roquinimex
• CAS No.: 84088-42-6
• Molecular Formula: C18H16N2O3
• Molecular Weight: 308.337
• Hs Code.: 2933790090
• Mol file: 84088-42-6.mol

Synonyms:ABR 212616;FCF 89;LS 2616;Linomide;PNU 212616;Roquinimex;

Chemical Property of Roquinimex

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 200-204°
• Refractive Index: 1.686
• Boiling Point: 436.187 °C at 760 mmHg
• Flash Point: 217.598 °C
• PSA: 62.54000
• Density: 1.357g/cm³
• LogP: 2.52070
• Storage Temp.: 2-8°C
• Solubility.: DMSO: 11 mg/mL

Purity/Quality:

98%,99%, ^*data from raw suppliers

Linomide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Description: Roquinimex is an immunomodulator with diverse biological activities. In vivo, roquinimex (80 mg/kg) increases the number of myocardial MHC class II-expressing cells, the ratio of cytotoxic to helper T cells, and survival and decreases necrotic lesion area in a mouse model of murine coxsackievirus B3-induced myocarditis. It induces IFN-γ production, reduces TNF-α and IL-1β production, prevents the development of proteinuria, and ameliorates nephritis in a mouse model of chronic graft versus host disease (GVHD). Roquinimex (300 mg/kg) decreases colonic myeloperoxidase (MPO) activity and mucosal damage in a mouse model of colitis induced by dextran sulfate (DSS; ). It also decreases tumor weight and tumor blood flow in a von Hippel-Lindau (VHL) type 2a paraganglioma mouse xenograft model.
• Uses: Biological response modifier; immunomodulator. An immunomodulator with antitumour properties. Inhibits T-cell apoptosis in vivo; also inhibits angiogenesis in rats

Technology Process of Roquinimex

There total 9 articles about Roquinimex 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: 98.6%

N-methylaniline (100-61-8) + 4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid methyl ester (84088-50-6) → roquinimex (84088-42-6)

Guidance literature:

In cyclohexane; for 2.5h; Solvent; Reflux; Molecular sieve;

Reference yield: 83.0%

ethyl 4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate (57513-54-9) + N-methylaniline (100-61-8) → roquinimex (84088-42-6)

Guidance literature:

In toluene; for 6h; Heating;

DOI:10.1021/jm031044w

Reference yield: 76.0%

1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylic acid (57931-81-4) + N-methylaniline (100-61-8) → roquinimex (84088-42-6)

Guidance literature:

With dicyclohexyl-carbodiimide; In toluene; at 80 - 85 ℃; for 2h; Concentration; Large scale;

DOI:10.1021/op049904l

upstream raw materials:

N-Methylisatoic anhydride

methyl 3-(N-methyl-N-phenylamino)-3-oxopropanoate

ethyl 4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate

N-methylaniline

Downstream raw materials:

N-(4-fluorophenyl)-1,2-dihydro-4-hydroxy-1-methyl-2-oxoquinoline-3-carboxamide

Refernces

• 1、 Khan, Saeed R.,Mhaka, Annastasiah,Pili, Roberto,Isaacs, John T.. "Modified synthesis and antiangiogenic activity of Linomide". . p. 451 - 452. Retrieved 2001.
• 2、 -. "1,2-DIHYDRO-4-HYDROXY-2-OXO-QUINOLINE-3-CARBOXANILIDES AS AHR ACTIVATORS.". Page/Page column 30. . Retrieved 2012/05/04.