54675-23-9

Usage

Uses

Used in Organic Synthesis:
6-broMo-4-hydroxyquinolin-2(1H)-one is used as an organic synthesis intermediate for the production of various chemical compounds. Its unique structure allows it to be a key component in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 6-broMo-4-hydroxyquinolin-2(1H)-one is used as a pharmaceutical intermediate. It plays a crucial role in the development of new drugs and medicines, contributing to the advancement of pharmaceutical research and innovation.
Used in Laboratory Research and Development:
6-broMo-4-hydroxyquinolin-2(1H)-one is employed in laboratory research and development processes, where it is used to study its properties, reactions, and potential applications in various fields. This helps researchers to better understand its behavior and develop new methods for its utilization.
Used in Chemical Production Processes:
6-broMo-4-hydroxyquinolin-2(1H)-one is also used in chemical production processes, where it is incorporated into the manufacturing of various chemical products. Its presence in these processes aids in the creation of new and improved chemical compounds for various applications.

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 
• 79612-79-6 ethyl 3-((4-bromophenyl)amino)-3-oxopropanoate 
• 95262-09-2 3-[(4-bromophenyl)amino]-3-oxopropanoic acid 
• 2033-24-1 cycl-isopropylidene malonate 

Downstream Products

• 80356-47-4 4-benzylamino-1H-quinolin-2-one 
• 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 

Relevant academic research and scientific papers

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.

Identification and molecular modeling of new quinolin-2-one thiosemicarbazide scaffold with antimicrobial urease inhibitory activity

Abstract: A new series of 6-substituted quinolin-2-one thiosemicarbazides 6a–j has been synthesized. The structure of the target compounds was proved by different spectroscopic and elemental analyses. All the designed final compounds were evaluated for their in vitro activity against the urease-producing R. mucilaginosa and Proteus mirabilis bacteria as fungal and bacterial pathogens, respectively. Moreover, all compounds were in vitro tested as potential urease inhibitors using the cup-plate diffusion method. Compounds 6a and 6b were the most active with (IC50 = 0.58 ± 0.15 and 0.43 ± 0.09?μM), respectively, in comparison with lead compound I (IC50 = 1.13 ± 0.00?μM). Also, the designed compounds were docked into urease proteins (ID: 3LA4 and ID: 4UBP) using Open Eye software to understand correctly about ligand–receptor interactions. The docking results revealed that the designed compounds can interact with the active site of the enzyme through multiple strong hydrogen bonds. Moreover, rapid overlay of chemical structures’ analysis was described to understand the 3D QSAR of synthesized compounds as urease inhibitors. The results emphasize the importance of polar thiosemicarbazide directly linked to 6-substituted quinolone moieties as promising antimicrobial urease inhibitors. Graphic abstract: [Figure not available: see fulltext.]

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.

HETEROARYL LINKED QUINOLINYL MODULATORS OF RORγT

The present invention comprises compounds of Formula I wherein: R1, R2, R3, R4, R5, R6, R7, R8, and R9 are defined in the specification, The invention also comprises a method of treating or ameliorating a syndrome, disorder or disease, wherein said syndro

SECONDARY ALCOHOL QUINOLINYL MODULATORS OF RORyt

The present invention comprises compounds of FormulaI.wherein:R1, R2, R3, R4, R5, R6, R7, R8, and R9are defined in the specification.The invention also comprises a method of treating or ameliorating a syndrome, disorder or disease, wherein said syndrome, disorder or disease is rheumatoid arthritis or psoriasis. The invention also comprises a method of modulating RORγt activity in a mammal by administration of a therapeutically effective amount of at least one compound of claim 1.

SECONDARY ALCOHOL QUINOLINYL MODULATORS OF RORyt

The present invention comprises compounds of Formula I. wherein: R1, R2, R3, R4, R5, R6, R7, R8, and R9 are defined in the specification. The invention also comprises a method of treating or ameliorating a syndrome, disorder or disease, wherein said syndrome, disorder or disease is rheumatoid arthritis or psoriasis. The invention also comprises a method of modulating RORγt activity in a mammal by administration of a therapeutically effective amount of at least one compound of claim 1.

HETEROARYL LINKED QUINOLINYL MODULATORS OF ROR?T

The present invention comprises compounds of Formula I wherein: R1, R2, R3, R4, R5, R6, R7, R8, and R9 are defined in the specification, The invention also

HETEROARYL LINKED QUINOLINYL MODULATORS OF RORgammat

The present invention comprises compounds of Formula I. wherein: R1, R2, R3, R4, R5, R6, R7 R8, and R9 are defined in the specification. The invention also

SECONDARY ALCOHOL QUINOLINYL MODULATORS OF RORyt

The present invention comprises compounds of Formula I. Formula I wherein: R1, R2, R3, R4, R5, R6, R7, R8, and R9 are defined in the specification. The invention also comprises a method of treating or ameliorating a syndrome, disorder or disease, wherein said syndrome, disorder or disease is rheumatoid arthritis or psoriasis. The invention also comprises a method of modulating RORγt activity in a mammal by administration of a therapeutically effective amount of at least one compound of claim 1.