54289-76-8

Upstream product

• 18706-63-3 4-Hydroxy-6-methyl-5,6-dihydro-2,5-dioxo-2H-pyrano<3,2-c>quinoline 
• 71509-15-4 6-methyl-4-methylamino-pyrano<3,2-c>quinolin-2,5(6H)-dione 
• 100-61-8 N-methylaniline 
• 85-91-6 Methyl N-methylanthranilate 
• 134369-72-5 2,3,5-trimethylfuro[3,2-c]quinolin-4(5H)-one 
• 1677-46-9 4-hydroxy-1-methyl-2(1H)-quinolone 
• 64-19-7 acetic acid 
• 134-20-3 2-carbomethoxyaniline 
• 26138-64-7 4-hydroxy-3-acetyl-1H-quinoline-2-one 
• 74-88-4 methyl iodide 

Downstream Products

• 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 
• 1677-46-9 4-hydroxy-1-methyl-2(1H)-quinolone 
• 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 
• 122476-75-9 4-hydroxy-3-(2-methyl-4-oxo-3-phenylthiazolidin-2-yl)-1-methylquinolin-2-one 
• 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 
• 14944-99-1 3-ethyl-4-hydroxy-1-methylquinolin-2(1H)-one 
• 93873-16-6 1-methyl-3-[1-(2-phenylhydrazono)ethyl]-4-hydroxyquinolin-2(1H)-one 
• 127855-74-7 3-acetyl-1-methyl-4-tolylsulfonyl-2(1H)-quinolone 
• 1063696-18-3 (2E)-1-(1-methyl-4-hydroxyquinolin-2(1H)-one-3-yl)-3-(4-chlorophenyl)-2-propen-1-one 
• 1063696-16-1 (2E)-1-(1-methyl-4-hydroxyquinolin-2(1H)-one-3-yl)-3-(4-chlorophenyl)-2-propen-1-one 

Relevant academic research and scientific papers

An Efficient New Route for the Synthesis of Some 3-Hterocyclylquinolinones via Novel 3-(1,2-Dihydro-4-hydroxy-1-methyl-2-oxoquinolin-3-yl)-3-oxopropanal and Their Antioxidant Screening

3-(4-hydroxy-1-methylquinoline-3-yl)-3-oxoproponal (5) was synthesized from 3-[(E)-3-(dimethylamino)-2-propenoyl]-4-hydroxy-1-methyl-2(1H)-quinolinone (3) and was utilized as a starting precursor material. A convenient new route to functionalized 3-hetero

Robust synthesis of linear and angular furoquinolines using Rap–stoermer reaction

We have synthesized novel linear and angular furoquinolines via the Rap–Stoermer reaction by conventional as well as microwave method that furnished an enhanced yield. Initially, we synthesized linear furo[2,3-b]quinolines from 3-acetyl-6-chloro-4-phenyl-

Synthesis, photooxygenation, and characterization of new angular furoquinolinone derivatives, a new furocoumarin bioisoster

Synthesis of angular furoquinolinone derivatives with a new skeleton structure was accomplished via Williamson reaction of hydroxyquinolinones with α-haloketones, such as 3-chloro-2-butanone and phenacyl bromide, followed by treatment with polyphosphoric

Novel quinolinone–pyrazoline hybrids: synthesis and evaluation of antioxidant and lipoxygenase inhibitory activity

Abstract: The present project deals with the investigation of structure–activity relationship of several quinolinone–chalcone and quinolinone–pyrazoline hybrids, in an effort to discover promising antioxidant and anti-inflammatory agents. In order to accomplish this goal, four bioactive hybrid quinolinone–chalcone compounds (8a–8d) were synthesized via an aldol condensation reaction, which were then chemically modified, forming fifteen new pyrazoline analogues (9a–9o). All the synthesized analogues were in vitro evaluated in terms of their antioxidant and soybean lipoxygenase (LOX) inhibitory activity. Among all the pyrazoline derivatives, compounds 9b and 9m were found to possess the best combined activity, whereas 9b analogue exhibited the most potent LOX inhibitory activity, with IC50 value 10?μM. The in silico docking results revealed that the synthetic pyrazoline analogue 9b showed high AutoDock Vina score (? 10.3?kcal/mol), while all the tested derivatives presented allosteric interactions with the enzyme. Graphic Abstract: [Figure not available: see fulltext.]

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

Synthesis and Evaluation of 4-Hydroxycoumarin Imines as Inhibitors of Class II Myosins

Inhibitors of muscle myosin ATPases are needed to treat conditions that could be improved by promoting muscle relaxation. The lead compound for this study ((3-(N-butylethanimidoyl)ethyl)-4-hydroxy-2H-chromen-2-one; BHC) was previously discovered to inhibit skeletal myosin II. BHC and 34 analogues were synthesized to explore structure-activity relationships. The properties of analogues, including solubility, stability, and toxicity, suggest that the BHC scaffold may be useful for developing therapeutics. Inhibition of actin-activated ATPase activity of fast skeletal and cardiac muscle myosin II, inhibition of skeletal muscle contractility ex vivo, and slowing of in vitro actin-sliding velocity were measured. Several analogues with aromatic side arms showed improved potency (half-maximal inhibitory concentration (IC50) 1 μM) and selectivity (≥12-fold) for skeletal myosin versus cardiac myosin compared to BHC. Several analogues blocked neurotransmission, suggesting that they are selective for nonmuscle myosin II over skeletal myosin. Competition and molecular docking studies suggest that BHC and blebbistatin bind to the same site on myosin.

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.

Novel 'quinolone' metal complexes: Synthesis and spectroscopic studies of Mg(II), Zn(II) and Ba(II) complexes with N-methyl (or NH)-3-acetyl-4-hydroxy quinolin-2-one ligands

The complexation between N-methyl-3-acetyl-4-hydroxyquinolin-2-one (NMeQuin) and N-H-3-acetyl-4-hydroxy quinolin-2-one (NHQuin) with MgCl 2, ZnCl2 and BaCl2 has been accomplished. The structure of the resulting complexes 1-5 has been elucidated through elemental analyses, FT-IR and 1H/13C NMR Spectroscopy and Mass Spectrometry. The spectroscopic data show complexes of the general formula Mg2(OH)L3(H2O)z and ML 2(H2O)z where: M = Zn(II) and Ba(II), L = NMeQuin, NHQuin and z = 2,4.

Synthesis, crystal structure and spectroscopic studies of 3- hydrazono- and 3-hydroxyiminoquinolin-2-ones

3-(Hydrazonoethyl)quinolinones 6-11, 13 and 3- (hydroxyiminoethyl)quinolinones 14, 15 are prepared by a condensation reaction of 3-acetylquinolinones 4, 5 with a variety of 1,2-(bis)nucleophiles. The structures of the isolated compounds have been elucidated using 1H and 13C nmr spectroscopy. X-ray diffraction studies of compound 14 were also performed.

Studies with polyfunctionally substituted heteroarenes: New synthesis of benzo [c] quinolinones and pyrano [3,2-c] quinoline derivatives

Nitration, bromination and acetylation of 4 - hydroxypyranoquinolines 1 yielded 3-nitro-, 3-bromo, and 3-acetylpyranoquinolines 3,5,8. Hyrolysis of 3, 5 and 8 with 2N NaOH afforded 3-nitroacetyl, 3-bromoacetyl and 3- acetylquinolines 4, 6 and 7 respectively. Formylation of 1 or 7 gave 3- formyl pyranoquinolines 9a-c. Reactions of 8 with 2 afforded benzo [c] quinolines 11 and 12. Treatment of 1, 24 or 7 with the ylidene 21 resulted in the formation of pyranoquinolines 25.