1207-81-4

Usage

Uses

Used in Organic Synthesis:
4-CHLORO-2-METHYL-6-NITROQUINOLINE is used as a building block in the synthesis of various pharmaceuticals, agrochemicals, and dyes, due to its versatile chemical structure and reactivity.
Used in Pharmaceutical Industry:
4-CHLORO-2-METHYL-6-NITROQUINOLINE is used as an intermediate in the development of new drugs, leveraging its potential antimicrobial, antifungal, and cytotoxic properties for therapeutic applications.
Used in Anticancer Research:
In the field of oncology, 4-CHLORO-2-METHYL-6-NITROQUINOLINE is used as a compound of interest in cancer cell research for its significant activity against certain types of cancer cells, as demonstrated in preliminary studies.
Used in Agrochemical Industry:
4-CHLORO-2-METHYL-6-NITROQUINOLINE is utilized in the agrochemical sector for the development of new pesticides and other agricultural chemicals, capitalizing on its potential to control pests and diseases in crops.
Used in Dye Industry:
4-CHLORO-2-METHYL-6-NITROQUINOLINE is also used in the dye industry for the creation of new dyes, taking advantage of its chemical properties to produce a range of colorants for various applications.

InChI:InChI=1/C10H7ClN2O2/c1-6-4-9(11)8-5-7(13(14)15)2-3-10(8)12-6/h2-5H,1H3

Upstream product

• 613-30-9 2-methyl-6-nitroquinoline 
• 6287-35-0 3-phenylaminobut-2-enoic acid ethyl ester 
• 1336-21-6 ammonium hydroxide 
• 1207-82-5 2-methyl-6-nitroquinoline-4-ol 
• 100-01-6 4-nitro-aniline 
• 112219-43-9 2-methyl-6-nitro-1H-quinolin-4-one 
• 4295-06-1 4-chloro-2-methylquinoline 
• 607-67-0 4-hydroxy-2-methylquinoline 

Downstream Products

• 99185-71-4 4-amino-2-methyl-6-nitroquinoline 
• 7511-77-5 N-(4-amino-2-methylquinolin-6-yl)-2-phenylacetamide 
• 1621143-40-5 N-(3,4,5-trimethoxyphenyl)-2-methyl-6-nitroquinolin-4-amine 
• 1621143-39-2 N-(3-methoxyphenyl)-2-methyl-6-nitroquinolin-4-amine 
• 1621143-38-1 N-(3-ethynylphenyl)-2-methyl-6-nitroquinolin-4-amine 
• 1621143-37-0 N-(3-(trifluoromethyl)phenyl)-2-methyl-6-nitroquinolin-4-amine 
• 1621143-36-9 N-(3-methylphenyl)-2-methyl-6-nitroquinolin-4-amine 
• 1621143-35-8 N-(3-bromo-4-fluorophenyl)-2-methyl-6-nitroquinolin-4-amine 

Relevant academic research and scientific papers

Synthesis of 6-methylbenzo-[b]pyrido[3,2-f][1,6]naphthyridines from 4-chloro-2-methylquinoline

4-Chloro-2-methylquinolines in reaction with 3-aminopyridine yielded 4-quinolinamines, which upon cyclisation under Vilsmeier-Haak conditions afforded the title compounds. 2005 Springer Science+Business Media, Inc.

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.

The synthesis and biological evaluation of new DNA-directed alkylating agents, phenyl N-mustard-4-anilinoquinoline conjugates containing a urea linker

We synthesized a series of phenyl N-mustard-4-anilinoquinoline conjugates to study their antitumorigenic effects. These agents were prepared by the condensation of 4-[N,N-bis(2-chloroethyl)amino]phenyl isocyanate with 6-amino-4-methylamino or 4-anilinoquinolines. The structure-activity relationship (SAR) studies revealed that the C2-methylquinoline derivatives (18a-o) were generally more cytotoxic than the C2-phenylquinoline conjugates (23a-d) in inhibiting the cell growth of various human tumor cell lines in vitro. However, the methylamino or aniline substituents at C4 of quinoline did not influence the cytotoxic effects. The title conjugates were capable of inducing DNA cross-linking and promoting cell-cycle arrest at the G2/M phase. This study demonstrates that phenyl N-mustard-4-anilinoquinoline conjugates are generally more potent than phenyl N-mustard-4-anilinoquinazoline conjugates against the cell growth of various tumor cell-lines.

Small molecule inhibitors of anthrax lethal factor toxin

This manuscript describes the preparation of new small molecule inhibitors of Bacillus anthracis lethal factor. Our starting point was the symmetrical, bis-quinolinyl compound 1 (NSC 12155). Optimization of one half of this molecule led to new LF inhibitors that were desymmetrized to afford more drug-like compounds.

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.