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Usage

Uses

Used in Pharmaceutical Industry:
4-Hydroxy-6-Methyl-2H-Pyrano[3,2-c]Quinoline-2,5(6H)-Dione is used as a potential cancer treatment agent due to its cytotoxic properties, which can target and eliminate cancer cells. Its structure and characteristics make it a candidate for further exploration in oncology research.
Used in Antibacterial Applications:
In the field of antimicrobial agents, 4-Hydroxy-6-Methyl-2H-Pyrano[3,2-c]Quinoline-2,5(6H)-Dione is utilized for its potential antibacterial properties, offering a possible solution in combating bacterial infections and contributing to the development of new antibiotics.
Used in Medicinal Chemistry Research:
4-Hydroxy-6-Methyl-2H-Pyrano[3,2-c]Quinoline-2,5(6H)-Dione serves as a subject of study in medicinal chemistry, where its unique structure and properties are investigated for the development of new drugs and therapeutic agents, particularly focusing on its antioxidant capabilities that could be beneficial in treating various diseases.

InChI:InChI=1/C13H9NO4/c1-14-8-5-3-2-4-7(8)12-11(13(14)17)9(15)6-10(16)18-12/h2-6,16H,1H3

Upstream product

• 100-61-8 N-methylaniline 
• 105-53-3 diethyl malonate 

Downstream Products

• 54289-76-8 3-acetyl-4-hydroxy-1-methyl-2(1H)-quinolone 
• 128405-27-6 2-Amino-6-(4-hydroxy-1-methyl-2-oxo-1,2-dihydro-quinolin-3-yl)-4-(4-methoxy-phenyl)-4H-pyran-3-carbonitrile 
• 128405-26-5 2-Amino-6-(4-hydroxy-1-methyl-2-oxo-1,2-dihydro-quinolin-3-yl)-4-phenyl-4H-pyran-3-carbonitrile 
• 128405-28-7 2-Amino-4-(4-chloro-phenyl)-6-(4-hydroxy-1-methyl-2-oxo-1,2-dihydro-quinolin-3-yl)-4H-pyran-3-carbonitrile 
• 128405-31-2 2-Amino-4-(4-chloro-phenyl)-6-(4-hydroxy-1-methyl-2-oxo-1,2-dihydro-quinolin-3-yl)-4H-pyran-3-carboxylic acid ethyl ester 
• 128405-29-8 2-Amino-6-(4-hydroxy-1-methyl-2-oxo-1,2-dihydro-quinolin-3-yl)-4-phenyl-4H-pyran-3-carboxylic acid ethyl ester 
• 128405-30-1 2-Amino-6-(4-hydroxy-1-methyl-2-oxo-1,2-dihydro-quinolin-3-yl)-4-(4-methoxy-phenyl)-4H-pyran-3-carboxylic acid ethyl ester 
• 71833-97-1 3-(N-benzylethanimidoyl)-4-hydroxy-1-methyl-2(1H)-quinolinone 
• 127855-79-2 3-acetyl-4-benzylamino-1-methyl-2(1H)-quinolone 
• 127855-74-7 3-acetyl-1-methyl-4-tolylsulfonyl-2(1H)-quinolone 
• 127855-77-0 3-acetyl-1-methyl-4-<(triphenylphosphoranylidene)amino>-2(1H)-quinolone 
• 1410922-08-5 1-methyl-4-hydroxy3-(8-(4-chlorophenyl)-6-oxo-6H-7,9-dicarbonitrilepyrido[1,2-b][1,2,4]triazin-2-yl)quinolin-2(1H)-one 
• 95855-01-9 (4-Acetoxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl) (5-Methyl-1,3,4-oxadiazol-2-yl) Ketone 
• 219479-27-3 (4-Hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl) (Tetrazol-5-yl) Ketone 

Relevant academic research and scientific papers

Synthesis, cytotoxic activity, ADMET and molecular docking study of quinoline-based hybrid compounds of 1,5-benzothiazepines

Some α,β-unsaturated ketones 4a-g of 3-acetyl-4-hydroxyquinolin-2(1H)-one were prepared by its reaction with (hetero)aromatic aldehydes with yields of 61-87% using piperidine as a catalyst. These ketones reacted with o-aminothiophenol in the presence of acetic acid to afford a series of new hybrid compounds, quinoline-benzothiazepine, 6a-g. The yields of benzothiazepines 6a-g were 62-85%. All the synthesized compounds 6a-g were screened for their in vitro anticancer activity against human hepatocellular carcinoma HepG2 and squamous cell carcinoma KB cancer lines. Compounds 6d and 6g had the best activity in the series, with IC50 values of 0.25 and 0.27 μg mL-1, respectively, against HepG2, and of 0.26 and 0.28 μM, respectively, against KB cell lines. ADMET properties showed that compounds 6c and 6g possessed drug-likeness behavior. Cross-docking results indicated that residues GLN778(A), DA12(F), and DG13(F) in the binding pocket were potential ligand binding hot-spot residues for compounds 6c and 6g. This journal is

Antitumor agents. 272. Structure-activity relationships and in vivo selective anti-breast cancer activity of novel neo-tanshinlactone analogues

Neo-tanshinlactone (1) and its previously reported analogues, such as 2, are potent and selective in vitro antibreast cancer agents. The synthetic pathway to 2 was optimized from seven to five steps, with a better overall yield. Structure-activity relationships studies on these compounds revealed some key molecular determinants for this family of antibreast agents. Several derivatives (19-21 and 24) exerted potent and selective antibreast cancer activity with IC50 values of 0.3,0.2,0.1, and 0.1 μg/mL, respectively, against the ZR-75-1 cell lines. Compound 24 was 2- to 3-fold more potent than 1 against SK-BR-3 and ZR-75-1. Importantly, 21 exhibited high selectivity; it was 23 times more active against ZR-75-1 than MCF-7. Compound 20 had an approximately 12-fold ratio of SK-BR-3/MCF-7 selectivity. In addition, analogue 2 showed potent activity against a ZR-75-1 xenograft model, but not PC-3 and MDA-MB-231 xenografts, as well as high selectivity against breast cancer cell line compared with normal breast tissue-derived cell lines. Further development of lead compounds 19-21 and 24 as clinical trial candidates is warranted.

Rapid preparation of pyranoquinolines using microwave dielectric heating in combination with fractional product distillation

4-Hydroxy-6-methyl-2H-pyrano[3,2-c]quinoline-2,5(6H)-dione was prepared by microwave-assisted cyclocondensation of N-methylaniline with 2 equiv of diethyl malonate. Key to the success of the synthesis was the use of open vessel controlled microwave heating technology, allowing the simultaneous removal of the formed ethanol from the reaction mixture by fractional distillation.

Transcription factor modulating compounds and methods of use thereof

Substituted benzoimidazole compounds useful as anti-infectives that decrease resistance, virulence, or growth of microbes are provided. Methods of making and using substituted benzoimidazole compounds, as well as pharmaceutical preparations thereof, in, e.g., reducing antibiotic resistance and inhibiting biofilms.

Transcription factor modulating compounds and methods of use thereof

Substituted benzoimidazole compounds useful as anti-infectives that decrease resistance, virulence, or growth of microbes are provided. Methods of making and using substituted benzoimidazole compounds, as well as pharmaceutical preparations thereof, in, e.g., reducing antibiotic resistance and inhibiting biofilms.

Organic Azides in Heterocyclic Synthesis, 11. Ring Closure of 3-Acetyl-4-azido-2-quinolones to Isoxazoloquinolones

Thermolysis of the 3-acetyl-4-azido-2-quinolone 6, which was obtained from the corresponding 4-tosyloxy derivative 5, afforded the ring closed isoxazoloquinolone 7 in good yield.