54675-23-9

Basic information

• Product Name: 6-broMo-4-hydroxyquinolin-2(1H)-one
• Synonyms: 6-broMo-4-hydroxyquinolin-2(1H)-one;6-broMo-4-hydroxy-291H)-quinolinone;6-Bromo-4-hydroxy-2(1H)-quinolinone;6-Bromo-4-hydroxycarbostyril;6-Bromo-4-hydroxyquinolin-2(1H);6-bromoquinoline-2,4-diol
• CAS NO: 54675-23-9
• Molecular Formula: C₉H₆BrNO₂
• Molecular Weight: 240.05344
• Mol File: 54675-23-9.mol
• Article Data: 18

Chemical Properties

• Melting Point: 211-212 °C
• Boiling Point: 451.3±45.0 °C(Predicted)
• Appearance: /
• Density: 1.801±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: 6-broMo-4-hydroxyquinolin-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-broMo-4-hydroxyquinolin-2(1H)-one(54675-23-9)
• EPA Substance Registry System: 6-broMo-4-hydroxyquinolin-2(1H)-one(54675-23-9)

Safety Data

• Hazardous Substances Data: 54675-23-9(Hazardous Substances Data)

Usage

Uses

6-broMo-4-hydroxyquinolin-2(1H)-one can be used as organic synthesis intermediates and pharmaceutical intermediates, mainly used in laboratory research and development processes and chemical production processes.

Synthesis

Literature [Synthetic Communications 2010, 40, 732] in accordance with the general method described, 4-bromoaniline (30.0 g, 174 mmol) and 2,2-dimethyl-l, 3-dioxane-4,6-dione ( 25.1 g, was heated in 174 mmol) in 80 for 1.5 hours, cooled to ambient temperature, 3 - ((4-bromophenyl) amino) -3-oxo-propane to give the acid.By removing the acetone by-product under vacuum to give the intermediate product as a dry solid.It was added to Eaton's Reagent (100 mL) to the solid, the mixture obtained in and then heated to 70 overnight, cooled to room temperature.The mixture was poured into water, the brown precipitate was filtered, and rinsed with water.With ethanol, the brown precipitate tree illustration in the tube, and then filtered to give the title compound as a light brown solid.

Upstream product

• 106-40-1 4-bromo-aniline 
• 105-53-3 diethyl malonate 
• 2033-24-1 cycl-isopropylidene malonate 
• 79612-79-6 ethyl 3-((4-bromophenyl)amino)-3-oxopropanoate 
• 95262-09-2 3-[(4-bromophenyl)amino]-3-oxopropanoic acid 

Downstream Products

• 406204-90-8 6-bromo-2,4-dichloroquinoline 
• 1599529-42-6 4-((6-bromo-2,4-dichloroquinolin-3-yl)methyl)benzonitrile 
• 1599529-43-7 4-((6-bromo-4-chloro-2-methoxyquinolin-3-yl)methyl)benzonitrile 
• 1599524-81-8 (6-bromo-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)(phenyl)iodoniumtrifluoromethane sulfonate 

Relevant articles and documents

One-step Synthesis of 3-Unsubstituted 4-Hydroxy-2(1H)-Quinoline

3-Unsubstituted 4-hydroxy-2(1H)-quinolone (DHQ) derivatives were synthesized from aniline derivatives and diethyl malonate at low temperature using AlCl3 as catalyst and Eaton reagent as acidic environment. A reaction mechanism was proposed and elucidated. Different synthetic intermediates are specially prepared or purified and used to understand the reaction and validation mechanism.

Novel Pyrazoloquinolin-2-ones: Design, synthesis, docking studies, and biological evaluation as antiproliferative EGFR-TK inhibitors

Two new series of diethyl 2-[2-(substituted-2-oxo-1,2-dihydroquinolin-4-yl)hydrazono]-succinates 6a-g and 1-(2-oxo-1,2-dihydroquinolin-4-yl)-1H-pyrazoles 7a-f have been designed and synthesized. The structures of the synthesized compounds were proved by IR, mass, NMR (2D) spectra and elemental analyses. The target compounds were evaluated for their in vitro cytotoxic activity against 60 cancer cell lines according to NCI protocol. Consequently, seven compounds were further examined against the most sensitive cell lines, leukemia CCRF-CEM, and MOLT-4. 5-Amino-1-(6-bromo-2-oxo-1,2-dihydroquinolin-4-yl)-1H-pyrazole-3,4-dicarbonitrile (7f) was the most active product, with IC50 = 1.35 uM and 2.42 uM against MOLT-4 and CCRF-CEM, respectively. Also, it showed a remarkable inhibitory activity compared to erlotinib on the EGFR TK with IC50 = 247.14 nM and 208.42 nM, respectively. Cell cycle analysis of MOLT-4 cells treated with 7f showed cell cycle arrest at G2/M phase (supported by Caspases, BAX and Bcl-2 studies) with a significant pro-apoptotic activity as indicated by annexin V-FITC staining. Moreover, the docking study indicated that both the pyrazole moiety and the quinolin-2-one ring showed good fitting into EGFR (PDB code: 1M17). In order to interpret SAR of the designed compounds, and provide a basis for further optimization, molecular docking of the synthesized compounds to known EGFR inhibitors was performed. The study illustrated the effect of several factors on the compounds’ activity.

HCV NS3 protease inhibitors

The present invention relates to macrocyclic compounds of formula (I) that are useful as inhibitors of the hepatitis C virus (HCV) NS3 protease, their synthesis, and their use for treating or preventing HCV infections.