1207-82-5

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
2-METHYL-6-NITROQUINOLIN-4(1H)-ONE is used as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals, leveraging its chemical structure to contribute to the development of new drugs and pesticides.
Used in Fluorescent Materials Production:
Due to its fluorescent properties, 2-METHYL-6-NITROQUINOLIN-4(1H)-ONE is utilized in the production of fluorescent probes and dyes, which find applications in research, diagnostics, and other specialized fields requiring fluorescence-based detection or imaging.
Used in Antimicrobial Applications:
2-METHYL-6-NITROQUINOLIN-4(1H)-ONE has been studied for its potential as an antifungal and antibacterial agent, indicating its use in the development of new antimicrobial treatments, although its exact mechanism of action and medicinal applications are still under investigation.
Used in Research and Development:
2-METHYL-6-NITROQUINOLIN-4(1H)-ONE's potential biological and pharmacological activities make it a valuable subject for ongoing research and development, particularly in exploring its mechanism of action and identifying new therapeutic uses.

InChI:InChI=1/C10H8N2O3/c1-6-4-10(13)8-5-7(12(14)15)2-3-9(8)11-6/h2-5H,1H3,(H,11,13)

Upstream product

• 607-67-0 4-hydroxy-2-methylquinoline 
• 141-97-9 ethyl acetoacetate 
• 100-01-6 4-nitro-aniline 
• 6287-35-0 3-phenylaminobut-2-enoic acid ethyl ester 

Downstream Products

• 1131-34-6 6-amino-2-methylquinolin-4-ol 
• 1207-81-4 4-chloro-2-methyl-6-nitroquinoline 
• 860191-74-8 N-(4-chlorophenyl)-2-methyl-6-nitroquinolin-4-amine 

Relevant academic research and scientific papers

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.

Syntheses and evaluation of new Quinoline derivatives for inhibition of hnRNP K in regulating oncogene c-myc transcription

Aberrant overexpression of heterogeneous nuclear ribonucleoprotein K (hnRNP K) is a key feature in oncogenesis and progression of many human cancers. hnRNP K has been found to be a transcriptional activator to up-regulate c-myc gene transcription, a critical proto-oncogene for regulation of cell growth and differentiation. Therefore, down-regulation of c-myc transcription by inhibiting hnRNP K through disrupting its binding to c-myc gene promoter is a potential approach for cancer therapy. In the present study, we synthesized and screened a series of Quinoline derivatives and evaluated their binding affinity for hnRNP K. Among these derivatives, (E)-1-(4-methoxyphenyl)-3-(4-morpholino-6-nitroquinolin-2-yl)prop-2-en-1-one (compound 25) was determined to be the first-reported hnRNP K binding ligand with its KD values of 4.6 and 2.6 μM measured with SPR and MST, respectively. Subsequent evaluation showed that the binding of compound 25 to hnRNP K could disrupt its unfolding of c-myc promoter i-motif, resulting in down-regulation of c-myc transcription. Compound 25 showed a selective anti-proliferative effect on human cancer cell lines with IC50 values ranged from 1.36 to 3.59 μM. Compound 25 exhibited good tumor growth inhibition in a Hela xenograft tumor model, which might be related to its binding with hnRNP K. These findings illustrated that inhibition of DNA-binding protein hnRNP K by compound 25 could be a new and selective strategy of regulating oncogene transcription instead of targeting promoter DNA secondary structures such as G-quadruplexes or i-motifs.

Synthesis of 2-, 3- or 4-phenylsubtituted chalcones based on 4-phenylamino-6-nitro-2-[(e)-2-phenylvinyl]quinoline, evaluation of their antimicrobial and antifungal activity

A series of thirteen (2E)-1-[4-({6-nitro-2-[(E)-2-phenylvinyl]quinolin-4-yl}amino)phenyl]-3-[(substituted) phenyl]prop-2-en-1-ones (5a-5m) were synthesized by five-step synthesis starting from 4-nitroaniline via 2-methyl-6-nitroquinolin-4-ol (2), 4-chloro-2-methyl-6-nitroquinoline (3), 4-chloro-6-nitro-2-[(E)-2-phenylethenyl]quinoline (3), and 1-[4-({6-nitro-2-[(E)-2-phenylvinyl]quinolin-4-yl}amino)phenyl]ethanone (5), respectively. Final chalcones 6a-6m were synthetized from 4 by condensation reaction with corresponding benzaldehydes (unsubstituted, 2-, 3- and 4-methyl-, 2-, 3- and 4-methoxy-, 2- and 4-fluoro-, 2-, 3- and 4-chloro-, and 4-trifluoromethylbenzaldehyde, respectively). Chalcones 6a-6m were characterized by IR, 1H NMR and MS spectroscopy deflate, is not presented. Antimicrobial and antifungal activity of the compound 6 was studied against the four bacterial types (Staphylococcus aureus MTCC 96, Streptococcus pyogenes MTCC 443, Escherichia coli MTCC 442, Pseudomonas aeruginosa MTCC 441) and three different types fungal strains (Aspergillus Niger MTCC 282, Aspergillus clavatus MTCC1323, Candida albicans MTCC 227). From the above synthesized compounds the chalcones 6e, 6f, 6k, and 6m exhibited very good activity against studied gram-positive and gram-negative bacterial strains and compounds 6a, 6e, 6f, 6j 6k and 6m showed very good anti-fungal activity against fungi above.

Synthesis of 2-, 3- or 4-phenylsubtituted chalcones based on 4-phenylamino-6-nitro-2-[(E)-2-phenylvinyl]quinoline, evaluation of their antimicrobial and antifungal activity

A series of thirteen (2E)-1-[4-({6-nitro-2-[(E)-2-phenylvinyl]quinolin-4-yl}amino)phenyl]-3-[(substituted) phenyl]prop-2-en-1-ones (5a-5m) were synthesized by five-step synthesis starting from 4-nitroaniline via 2-methyl-6-nitroquinolin-4-ol (2), 4-chloro-2-methyl-6-nitroquinoline (3), 4-chloro-6-nitro-2-[(E)-2-phenylethenyl]quinoline (3), and 1-[4-({6-nitro-2-[(E)-2-phenylvinyl]quinolin-4-yl}amino)phenyl]ethanone (5), respectively. Final chalcones 6a-6m were synthetized from 4 by condensation reaction with corresponding benzaldehydes (unsubstituted, 2-, 3- and 4-methyl-, 2-, 3-and 4-methoxy-, 2- and 4-fluoro-, 2-, 3- and 4-chloro-, and 4-trifluoromethylbenzaldehyde, respectively). Chalcones 6a-6m were characterized by IR, 1H NMR and MS spectroscopy deflate, is not presented. Antimicrobial and antifungal activity of the compound 6 was studied against the four bacterial types (Staphylococcus aureus MTCC 96, Streptococcus pyogenes MTCC 443, Escherichia coli MTCC 442, Pseudomonas aeruginosa MTCC 441) and three different types fungal strains (Aspergillus Niger MTCC 282, Aspergillus clavatus MTCC1323, Candida albicans MTCC 227). From the above synthesized compounds the chalcones 6e, 6f, 6k, and 6m exhibited very good activity against studied gram-positive and gram-negative bacterial strains and compounds 6a, 6e, 6f, 6j 6k and 6m showed very good anti-fungal activity against fungi above.

Amide compounds and pharmaceutical compositions for inhibiting protein kinases, and methods for their use

Amide compounds that modulate and/or inhibit the activity of certain protein kinases are described. These compounds and pharmaceutical compositions containing them are capable of mediating tyrosine kinase signal transduction in order to modulate and/or inhibit unwanted cell proliferation. The invention is also directed to the therapeutic or prophylactic use of pharmaceutical compositions containing such compounds, and to methods of treating cancer as well as other disease states associated with unwanted angiogenesis and/or cellular proliferation, such as diabetic retinopathy, neovascular glaucoma, rheumatoid arthritis, and psoriasis, by administering effective amounts of such compounds.