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84088-42-6,MFCD00866331
Catalog No.:AA004SRV

84088-42-6 | Roquinimex

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5mg
≥98%
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$128.00   $89.00
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100mg
98%
in stock  
$193.00   $135.00
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250mg
98%
in stock  
$328.00   $230.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA004SRV
Chemical Name:
Roquinimex
CAS Number:
84088-42-6
Molecular Formula:
C18H16N2O3
Molecular Weight:
308.3312
MDL Number:
MFCD00866331
SMILES:
CN(C(=O)c1c(O)c2ccccc2n(c1=O)C)c1ccccc1
Properties
Properties
 
BP:
436.187°C at 760 mmHg  
Form:
Solid  
MP:
200-204℃  
Storage:
Keep in dry area;2-8℃;  

Computed Properties
 
Complexity:
522  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
23  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
2  
XLogP3:
2.7  

Downstream Synthesis Route

[1]Khan,SaeedR.;Mhaka,Annastasiah;Pili,Roberto;Isaacs,JohnT.[BioorganicandMedicinalChemistryLetters,2001,vol.11,#4,p.451-452]

[1]Jönsson,Stig;Andersson,Gunnar;Fex,Tomas;Fristedt,Tomas;Hedlund,Gunnar;Jansson,Karl;Abramo,Lisbeth;Fritzson,Ingela;Pekarski,Olga;Runström,Anna;Sandin,Helena;Thuvesson,Ingela;Björk,Anders[JournalofMedicinalChemistry,2004,vol.47,#8,p.2075-2088]

[2]Shi,Jiandong;Xiao,Zili;Ihnat,MichaelA.;Kamat,Chandrashekhar;Pandit,Bulbul;Hu,Zhigen;Li,Pui-Kai[BioorganicandMedicinalChemistryLetters,2003,vol.13,#6,p.1187-1189]

[1]Jönsson,Stig;Andersson,Gunnar;Fex,Tomas;Fristedt,Tomas;Hedlund,Gunnar;Jansson,Karl;Abramo,Lisbeth;Fritzson,Ingela;Pekarski,Olga;Runström,Anna;Sandin,Helena;Thuvesson,Ingela;Björk,Anders[JournalofMedicinalChemistry,2004,vol.47,#8,p.2075-2088]

[1]Jönsson,Stig;Andersson,Gunnar;Fex,Tomas;Fristedt,Tomas;Hedlund,Gunnar;Jansson,Karl;Abramo,Lisbeth;Fritzson,Ingela;Pekarski,Olga;Runström,Anna;Sandin,Helena;Thuvesson,Ingela;Björk,Anders[JournalofMedicinalChemistry,2004,vol.47,#8,p.2075-2088]

[2]Shi,Jiandong;Xiao,Zili;Ihnat,MichaelA.;Kamat,Chandrashekhar;Pandit,Bulbul;Hu,Zhigen;Li,Pui-Kai[BioorganicandMedicinalChemistryLetters,2003,vol.13,#6,p.1187-1189]

[3]Sjoevall,Sven;Hansen,Lars;Granquist,Bo[OrganicProcessResearchandDevelopment,2004,vol.8,#5,p.802-807]

[1]Jönsson,Stig;Andersson,Gunnar;Fex,Tomas;Fristedt,Tomas;Hedlund,Gunnar;Jansson,Karl;Abramo,Lisbeth;Fritzson,Ingela;Pekarski,Olga;Runström,Anna;Sandin,Helena;Thuvesson,Ingela;Björk,Anders[JournalofMedicinalChemistry,2004,vol.47,#8,p.2075-2088]

Literature

Title: H1521, a novel derivative of 4-hydroxyquinoline-3-carboxamide, suppresses the development of lupus in mice by inducing Th1 cytokine profile in T cells.

Journal: International immunopharmacology 20110401

Title: The long and winding road for the development of tasquinimod as an oral second-generation quinoline-3-carboxamide antiangiogenic drug for the treatment of prostate cancer.

Journal: Expert opinion on investigational drugs 20101001

Title: Roquinimex-mediated protection effect on the development of chronic graft-versus-host disease in mice is associated with induction of Th1 cytokine production and inhibition of proinflammatory cytokine production.

Journal: Life sciences 20071027

Title: Identification of ABR-215050 as lead second generation quinoline-3-carboxamide anti-angiogenic agent for the treatment of prostate cancer.

Journal: The Prostate 20061201

Title: Design, synthesis, and biological evaluation of novel 4-hydro-quinoline-3-carboxamide derivatives as an immunomodulator.

Journal: Bioorganic & medicinal chemistry letters 20050615

Title: Effect of Linomide on adhesion molecules, TNF-alpha, nitrogen oxide, and cell adhesion.

Journal: International immunopharmacology 20050201

Title: Interleukin-10 mediates the protective effect of Linomide by reducing CXC chemokine production in endotoxin-induced liver injury.

Journal: British journal of pharmacology 20041201

Title: Immunomodulation by roquinimex decreases the expression of IL-23 (p19) mRNA in the brains of herpes simplex virus type 1 infected BALB/c mice.

Journal: Clinical and experimental immunology 20040801

Title: Synthesis and biological evaluation of new 1,2-dihydro-4-hydroxy-2-oxo-3-quinolinecarboxamides for treatment of autoimmune disorders: structure-activity relationship.

Journal: Journal of medicinal chemistry 20040408

Title: Structure-activity relationships studies of the anti-angiogenic activities of linomide.

Journal: Bioorganic & medicinal chemistry letters 20030324

Title: Roquinimex inhibits dextran sodium sulfate-induced murine colitis.

Journal: Inflammation research : official journal of the European Histamine Research Society ... [et al.] 20030201

Title: Semliki Forest virus infection is enhanced in Th1-prone SJL mice but not in Th2-prone BALB/c mice during Linomide-induced immunomodulation.

Journal: Journal of neuroimmunology 20021101

Title: Quinoline-3-carbothioamides and related compounds as novel immunomodulating agents.

Journal: Bioorganic & medicinal chemistry letters 20020902

Title: The new orally active immunoregulator laquinimod (ABR-215062) effectively inhibits development and relapses of experimental autoimmune encephalomyelitis.

Journal: Journal of neuroimmunology 20020901

Title: Suppression of experimental autoimmune neuritis by ABR-215062 is associated with altered Th1/Th2 balance and inhibited migration of inflammatory cells into the peripheral nerve tissue.

Journal: Neuropharmacology 20020401

Title: Protective effect of Linomide on TNF-alpha-induced hepatic injury.

Journal: Journal of hepatology 20020201

Title: Effects of Linomide on immune cells and cytokines inhibit autoimmune pathologies of the central and peripheral nervous system.

Journal: International immunopharmacology 20010601

Title: The immunomodulator Linomide: role in treatment and prevention of autoimmune diabetes mellitus.

Journal: International immunopharmacology 20010601

Title: Relationship of urinary myelin basic protein-like material with cranial magnetic resonance imaging in advanced multiple sclerosis.

Journal: Archives of neurology 20010101

Title: Identification of cytochrome P4503A as the major subfamily responsible for the metabolism of roquinimex in man.

Journal: Xenobiotica; the fate of foreign compounds in biological systems 20000901

Title: Roquinimex, From Wikipedia

Title: Liu Q, et al. Roquinimex inhibits dextran sodium sulfate-induced murine colitis. Inflamm Res. 2003 Feb;52(2):64-8.

Title: Tian WZ, et al. Linomide (roquinimex) affects the balance between pro- and anti-inflammatory cytokines in vitro in multiple sclerosis. Acta Neurol Scand. 1998 Aug;98(2):94-101.

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Tags:84088-42-6 Molecular Formula|84088-42-6 MDL|84088-42-6 SMILES|84088-42-6 Roquinimex