15644-82-3

Basic information

• Product Name: 2,6-Dimethyl-4-quinolinol
• Synonyms: 2,6-DIMETHYL-4(1H)QUINOLINONE;2,6-DIMETHYLQUINOLIN-4-OL;2,6-DIMETHYL-4-QUINOLINOL;2,6-DIMETHYL-4-HYDROXYQUINOLINE;2,6-DIMETHYLQUINOLIN-4(1H)-ONE;AURORA 18115;4-HYDROXY-2,6-DIMETHYLQUINOLINE;2,6-dimethyl-1H-quinolin-4-one
• CAS NO: 15644-82-3
• Molecular Formula: C₁₁H₁₁NO
• Molecular Weight: 173.21
• Mol File: 15644-82-3.mol

Chemical Properties

• Melting Point: 283-287 °C
• Boiling Point: 299.3 °C at 760 mmHg
• Flash Point: 128.8 °C
• Appearance: /
• Density: 1.107 g/cm3
• Vapor Pressure: 0.00121mmHg at 25°C
• Refractive Index: 1.566
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2,6-Dimethyl-4-quinolinol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Dimethyl-4-quinolinol(15644-82-3)
• EPA Substance Registry System: 2,6-Dimethyl-4-quinolinol(15644-82-3)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-37/38-41
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 15644-82-3(Hazardous Substances Data)

Usage

Uses

Used in Veterinary Medicine:
2,6-Dimethyl-4-quinolinol is used as an anti-parasitic agent for the treatment of heartworm in dogs. It is effective in combating the parasitic infection, ensuring the health and well-being of the animals.
Used in Pharmaceutical Formulations:
2,6-Dimethyl-4-quinolinol is used as an active ingredient in pharmaceutical formulations, specifically targeting heartworm treatment in dogs. Its efficacy in treating this parasitic infection makes it a valuable component in veterinary medicine.
Used in Research and Development:
2,6-Dimethyl-4-quinolinol is also used in research and development for the discovery of new anti-parasitic agents and potential applications in other areas of medicine. Its chemical properties and effects on parasites make it an interesting compound for further study and potential development of new treatments.

InChI:InChI=1/C11H11NO/c1-7-3-4-10-9(5-7)11(13)6-8(2)12-10/h3-6H,1-2H3,(H,12,13)

Upstream product

• 75896-58-1 2,6-dimethyl-4-methoxyquinoline 
• 33240-21-0 ethyl 3-(p-tolylamino)but-2-enoate 
• 108-24-7 acetic anhydride 
• 103-89-9 4-Methylacetanilide 
• 141-97-9 ethyl acetoacetate 
• 106-49-0 p-toluidine 
• 88960-38-7 4-hydroxy-2,6-dimethyl-quinoline-3-carboxylic acid ethyl ester 

Downstream Products

• 29125-48-2 4-hydrazino-2,6-dimethylquinoline 
• 1033055-31-0 4-methyl-2-(3-methyl-1H-pyrazol-5-yl)aniline 
• 133933-28-5 diethyl 2-desamino-2-methyl-N¹-<(pivaloyloxy)methyl>-N¹⁰-propargyl-3,5,8-trideazafolate 
• 133933-14-9 2-desamino-2-methyl-N⁽¹⁰⁾-propargyl-3,5,8-tr ideazafolic acid 
• 6270-08-2 4-chloro-2,6-dimethylquinoline 
• 134255-48-4 6-Methyl-2-((E)-styryl)-quinolin-4-ol 
• 74767-13-8 2-{[1-(4-Acetylamino-phenyl)-meth-(Z)-ylidene]-amino}-benzoic acid 2,6-dimethyl-quinolin-4-yl ester 
• 74767-18-3 2-{[1-(4-Dimethylamino-phenyl)-meth-(Z)-ylidene]-amino}-benzoic acid 2,6-dimethyl-quinolin-4-yl ester 
• 74780-34-0 2-{[1-(4-Chloro-phenyl)-meth-(Z)-ylidene]-amino}-benzoic acid 2,6-dimethyl-quinolin-4-yl ester 
• 74767-09-2 2-{[1-(4-Hydroxy-phenyl)-meth-(Z)-ylidene]-amino}-benzoic acid 2,6-dimethyl-quinolin-4-yl ester 
• 74767-23-0 4-{[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-amino}-benzoic acid 2,6-dimethyl-quinolin-4-yl ester 
• 74767-26-3 4-{[1-(4-Acetylamino-phenyl)-meth-(E)-ylidene]-amino}-benzoic acid 2,6-dimethyl-quinolin-4-yl ester 
• 74767-33-2 4-{[1-(4-Dimethylamino-phenyl)-meth-(E)-ylidene]-amino}-benzoic acid 2,6-dimethyl-quinolin-4-yl ester 
• 74767-29-6 4-{[1-(4-Hydroxy-phenyl)-meth-(E)-ylidene]-amino}-benzoic acid 2,6-dimethyl-quinolin-4-yl ester 

Relevant articles and documents

Synthesis and identification of quinoline derivatives as topoisomerase I inhibitors with potent antipsoriasis activity in an animal model

Psoriasis is a chronic inflammatory and immune-mediated skin disease. Although certain agents have shown clinical success in treating psoriasis, development of safe and effective strategies for the treatment of this condition remains important. Research suggests that DNA topoisomerase I (Topo I)inhibitors may have potent psoriasis-ameliorating effects. Here, 25 quinoline derivatives were synthesized and identified as Topo I inhibitors. These compounds inhibited the 12–O–tetradecanoylphorbol-13-acetate-induced mouse ear inflammation. The most potent analogs, 5i and 5l, suppressed the expression of inflammatory cytokines in lipopolysaccharide-stimulated HaCaT cells. Additionally, the lead compounds significantly improved imiquimod-induced psoriasis-like inflammation in mice. Moreover, the expression levels of cytokines and inflammatory mediators, such as interleukin (IL)-17A, IL-22, IL-23, nuclear factor-κB subunit p65, tumor necrosis factor-α, and interferon-γ, were dramatically inhibited in the dorsal skin of 5i- and 5l-treated mice. These findings indicate that the inhibition of Topo I activity may potentially be an effective strategy for psoriasis treatment.

SAR and identification of 2-(quinolin-4-yloxy)acetamides as Mycobacterium tuberculosis cytochrome bc 1 inhibitors

A previous phenotypic screen by GSK identified 2-(quinolin-4-yloxy)acetamides as potent growth inhibitors of Mycobacterium tuberculosis (Mtb). We report the results of a preliminary structure-activity relationship (SAR) study of the compound class which has yielded more potent inhibitors. An Mtb cytochrome bd oxidase deletion mutant (cydKO) was found to be hypersensitive to most members of the compound library, while strains carrying single-nucleotide polymorphisms of the qcrB gene, which encodes a subunit of the menaquinol cytochrome c oxidoreductase (bc1) complex, were resistant to the library. These results identify that the 2-(quinolin-4-yloxy)acetamide class of Mtb growth inhibitors can be added to the growing number of scaffolds that target the M. tuberculosis bc1 complex.

N1-{4-[(10S)-Dihydroartemisinin-10-oxyl]}phenylmethylene-N 2-(2-methylquinoline-4-yl)hydrazine derivatives as antiplasmodial falcipain-2 inhibitors

A series of N1-{4-[(10S)-dihydroartemisinin- 10-oxyl]}phenylmethylene-N2-(2-methylquinoline-4-yl) hydrazine derivatives 9a-9n possessing 4-quinolylhydrazone and artemisinin cores were herein synthesized and evaluated for their activities against cysteine protease falcipain- 2 of Plasmodium falciparum. The structures were clearly confirmed by elemental analysis, 1H NMR, and mass spectra. The pharmacological results indicated that all compounds showed excellent activity against recombinant falcipain-2 (IC50 = 0.15-2.28 μM). The best one of this series was compound 9d (IC50 = 0.15 μM). The molecular docking results showed that the compound 9d made close contact with the key active site of cysteine protease falcipain-2.

Quinoline derivatives as antitubercular/antibacterial agents

A number of quinoline derivatives of known antibacterial agents have been prepared and tested against the micro-organisms S. coli, S. paratyphi B, S. aureus and in particular against Mycobacterium tuberculosis H37-Rv. It has not been possibfe to establish correlation between antibacterial and antitubercular activities of these compounds. However, the antitubercular effect at MIC of 5 μg/mL against H37Rv shows that many modified compounds are more inhibitory than the parent agents such as 3-aminophenol, sulphamethoxazole, sulphaphenazole, sulphathiazole and monoacetyldapsone; among these the most effective are those with substituents such as 6-methyl, 6-chloro, 6-ethoxy-, or 8-methoxy functions in quinoline moiety.