28563-22-6

Usage

Uses

Used in Pharmaceutical Industry:
4-Hydroxy-7-Methoxy-3-phenylquinolin-2(1H)-one is used as an intermediate in the production of pharmaceuticals for its potential role in the development of new drugs. Its presence in the synthesis process is crucial for creating compounds with therapeutic applications.
Used in Organic Compounds Synthesis:
In the field of organic chemistry, 4-HMQ is utilized as an intermediate for synthesizing various organic compounds, highlighting its versatility and importance in chemical research and development.
Used in Anti-inflammatory Applications:
4-Hydroxy-7-Methoxy-3-phenylquinolin-2(1H)-one is employed as an anti-inflammatory agent due to its potential biological activities. It may contribute to the management of inflammation-related conditions by reducing inflammation at the cellular level.
Used in Anti-cancer Applications:
As a drug candidate, 4-HMQ is used in anti-cancer research for its potential to combat cancer cells. Its anti-cancer properties are being investigated for efficacy in treating various types of cancer.
Used in Antioxidant Therapies:
4-Hydroxy-7-Methoxy-3-phenylquinolin-2(1H)-one is used as an antioxidant in the development of novel therapeutic agents. Its antioxidant properties may play a role in protecting cells from oxidative stress and related diseases.
Used in Disease Treatment Research:
4-HMQ is utilized as a potential drug candidate in the research for treatments of various diseases. Its biological activities are being explored for their potential to alleviate symptoms or cure specific pathological conditions.

InChI:InChI=1/C16H13NO3/c1-20-11-7-8-12-13(9-11)17-16(19)14(15(12)18)10-5-3-2-4-6-10/h2-9H,1H3,(H2,17,18,19)

Upstream product

• 536-90-3 m-Anisidine 
• 83-13-6 diethyl 2-phenylmalonate 
• 1227736-33-5 3-phenyl-7-methoxy-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)quinolin-2(1H)-one 
• 104-94-9 4-methoxy-aniline 

Downstream Products

• 1227736-33-5 3-phenyl-7-methoxy-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)quinolin-2(1H)-one 
• 28566-02-1 4,7-dihydroxy-3-phenylquinolin-2(1H)-one 
• 144603-88-3 6-Chloro-3-fluoro-7-methoxy-3-phenyl-1H-quinoline-2,4-dione 

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.

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

Discovery of novel quinoline-based estrogen receptor ligands using peptide interaction profiling

Traditional approaches to discovery of selective estrogen receptor modulators (SERMs) have relied on ER binding and cell-based estrogen response element-driven assays to identify compounds that are osteoprotective but nonproliferative in breast and uterin

SUBSTITUTED QUINOLINE COMPOUNDS FOR USE AS SELECTIVE ESTROGEN RECEPTOR MODULATOR

The present invention relates to novel compounds of Formula (I) with a variety of therapeutic uses, more particularly novel substituted quinoline compounds particularly useful for selective estrogen receptor modulation.

Synthesis and cytotoxic activity evaluation of indolo-, pyrrolo-, and benzofuro-quinolin-2(1H)-ones and 6-anilinoindoloquinoline derivatives.

Certain indolo-, pyrrolo-, and benzofuro-quinolin-2(1H)-ones 4a,b, 6, 8, 16a-c and 6-anilinoindoloquinoline derivatives 10a,b, 11a,b, 12a,b have been synthesized and evaluated in vitro against a 3-cell lines panel consisting of MCF7 (Breast), NCI-H460 (Lu

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