28563-21-5

Upstream product

• 104-94-9 4-methoxy-aniline 
• 83-13-6 diethyl 2-phenylmalonate 
• 1227736-32-4 3-phenyl-6-methoxy-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)quinolin-2(1H)-one 

Downstream Products

• 144603-48-5 3-Chloro-6-methoxy-3-phenyl-1H-quinoline-2,4-dione 
• 144603-17-8 3-bromo-6-methoxy-3-phenylquinoline-2,4(1H,3H)-dione 
• 1227736-32-4 3-phenyl-6-methoxy-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)quinolin-2(1H)-one 
• 1303613-89-9 6-methoxy-3-phenyl-3-(4-phenyl-1H-1,2,3-triazol-1-yl)quinoline-2,4(1H,3H)-dione 
• 1303613-90-2 3-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)-6-methoxy-3-phenylquinoline-2,4(1H,3H)-dione 
• 685893-24-7 2,4-dichloro-6-methoxy-3-phenylquinoline 
• 1286131-48-3 4-chloro-6-methoxy-3-phenylquinolin-2(1H)-one 
• 1286950-68-2 4-chloro-6-methoxy-3-phenylquinolin-2(1H)-one 
• 28566-01-0 4,6-dihydroxy-3-phenylquinolin-2(1H)-one 

Relevant academic research and scientific papers

Design, synthesis and antitubercular potency of 4-hydroxyquinolin-2(1H)-ones

In this study, a 50-membered library of substituted 4-hydroxyquinolin-2(1H)-ones and two closely related analogues was designed, scored in-silico for drug likeness and subsequently synthesized. Thirteen derivatives, all sharing a common 3-phenyl substituent showed minimal inhibitory concentrations against Mycobacterium tuberculosis H37Ra below 10 μM and against Mycobacterium bovis AN5A below 15 μM but were inactive against faster growing mycobacterial species. None of these selected derivatives showed significant acute toxicity against MRC-5 cells or early signs of genotoxicity in the Vitotox assay at the active concentration range. The structure activity study relation provided some insight in the further favourable substitution pattern at the 4-hydroxyquinolin-2(1H)-one scaffold and finally 6-fluoro-4-hydroxy-3-phenylquinolin-2(1H)-one (38) was selected as the most promising member of the library with a MIC of 3.2 μM and a CC50 against MRC-5 of 67.4 μM.

3-aryl-6-methoxy-2-oxo-1,2-dihydroquinoline-4-carbonitriles as solvent and pH independent green fluorescent dyes

Highly fluorescent and stable 3-aryl-6-methoxy-2-oxoquinoline-4- carbonitriles 6 (λexc = 408 nm and λem = 510 nm) were synthesized starting from appropriate arylmalonates 2. Ring closure reaction with p-anisidine gave 4-hydroxyquinol

Copper(I)-catalyzed [3+2] cycloaddition of 3-azidoquinoline-2,4(1H,3H)- diones with terminal alkynes

3-Azidoquinoline-2,4(1H,3H)-diones 1,which are readily available from 4-hydroxyquinolin-2(1H)-ones 4 via 3-chloroquinoline-2,4(1H,3H)-diones 5, afford, in copper(I)-catalyzed [3+2] cycloaddition reaction with terminal acetylenes, 1,4-disubstituted 1,2,3-t

Selective formation of glycosidic linkages of N-unsubstituted 4-hydroxyquinolin-2-(1H)-ones

A comparative study for selective glucosylation of N-unsubstituted 4-hydroxyquinolin-2(1H)-ones into 4-(tetra-O-acetyl-β-d-glucopyranosyloxy)quinolin-2(1H)-ones is reported. Four glycosyl donors including tetra-O-acetyl-α-d-glucopyranosyl bromide, β-d-glu

Rapid microwave-enhanced synthesis of 4-hydroxyquinolinones under solvent-free conditions

3-Aryl-4-hydroxyquinolin-2(1H)-ones are potent and selective glycine-site NMDA receptor antagonists of pharmaceutical interest. A novel microwave-enhanced synthesis of such quinolinones under solvent-free conditions has been developed. The quinolinones ar

Substituent effects on absorption and fluorescence spectra of carbostyrils

Absorption and fluorescence spectra as well as quantum yields of a series of differently substituted carbostyrils (quinolin-2(1H)-ones) are reported. Especially for compounds containing donor substituents in position 6, substantial bathochromic shifts (comparable to analogous coumarins) of both absorption as well as fluorescence transitions are obtained. High absorption intensities and quantum yields are found for 7-donor substituted isomers. Semiempirical molecular orbital calculations (AMI for structures, ZINDO for electronic transition energies) prove to be a suitable tool for the prediction of absorption and fluorescence properties of these compounds. Ab initio and density functional calculations establish the lactam form as the dominant tautomer of the parent quinolin-2(1H)-one.

Oxidative Hydroxylation of Heterocyclic β-Dicarbonyl Compounds

3-Substituted 4-hydroxy-2-quinolones (1), 5-substituted barbituric acids (3) and 4-substituted pyrazolidine-2,4-diones were oxidized to yield the corresponding hydroxyderivatives 2,4 or 9, respectively. - Keywords: 5-Hydroxy-2,4,6-pyrimidine-triones; 4-Hy