51085-91-7

Basic information

• Product Name: 6-BROMOCHROMONE-3-CARBOXYLIC ACID
• Synonyms: 6-BROMO-4-OXO-4H-CHROMENE-3-CARBOXYLIC ACID;6-BROMOCHROMONE-3-CARBOXYLIC ACID;RARECHEM AL BE 0439
• CAS NO: 51085-91-7
• Molecular Formula: C₁₀H₅BrO₄
• Molecular Weight: 269.05
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
• Mol File: 51085-91-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 191-193℃
• Boiling Point: 397.8 °C at 760 mmHg
• Flash Point: 194.4 °C
• Appearance: /
• Density: 1.874 g/cm³
• PKA: 2.12±0.20(Predicted)
• CAS DataBase Reference: 6-BROMOCHROMONE-3-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMOCHROMONE-3-CARBOXYLIC ACID(51085-91-7)
• EPA Substance Registry System: 6-BROMOCHROMONE-3-CARBOXYLIC ACID(51085-91-7)

Safety Data

• Hazardous Substances Data: 51085-91-7(Hazardous Substances Data)

Usage

Description

6-Bromochromone-3-carboxylic acid, also known as 6-Bromo-3-carboxychromone, is a chemical compound with the molecular formula C10H5BrO4. It is a derivative of chromone and contains a carboxylic acid functional group. 6-Bromochromone-3-carboxylic acid is characterized by its unique structure and reactivity, making it a valuable tool in the field of organic chemistry and drug discovery.

Uses

Used in Pharmaceutical Drug Development:
6-Bromochromone-3-carboxylic acid is used as a reactant in organic synthesis and medicinal chemistry for the development of pharmaceutical drugs. Its potential biological activities, such as anti-inflammatory, antimicrobial, and anticancer properties, make it a promising candidate for the creation of new therapeutic agents.
Used in Antioxidant Research:
6-Bromochromone-3-carboxylic acid is also investigated for its potential role as an antioxidant. Its ability to combat oxidative stress and protect cells from damage makes it a valuable compound in the study and treatment of various diseases associated with oxidative stress.
Used in Disease Treatment:
6-Bromochromone-3-carboxylic acid has been studied for its potential in treating various diseases. Its unique structure and reactivity allow it to be a versatile component in the development of new treatments and therapies for a range of health conditions.

Upstream product

• 52817-12-6 6-bromo-4-oxo-4H-chromene-3-carbaldehyde 
• 1450-75-5 5-Bromo-2-hydroxyacetophenone 

Relevant articles and documents

Multi-target-directed ligands for Alzheimer's disease: Discovery of chromone-based monoamine oxidase/cholinesterase inhibitors

There has been a substantial research effort to design multi-target ligands for the treatment of Alzheimer's disease (AD), an approach that is moved by the knowledge that AD is a complex and multifactorial disease affecting many linked to pathological pathways. Accordingly, we have devoted efforts to develop multi-target ligands based on the chromone scaffold. As a result, a small library of chromone derivatives was synthesized and screened towards human cholinesterases and monoamine oxidases. Compounds 2-(dimethylamino)ethyl (E)-3-(4-oxo-2-(p-methylphenlcarbamoyl)-4H-chromen-6-yl)acrylate (9a) and 2-(dimethylamino)ethyl (E)-3-(4-oxo-3-(phenylcarbamoyl)-4H-chromen-6-yl)acrylate (23a) were identified as the most promising multi-target inhibitors of the series. Compound 9a acted as a potent, selective and bifunctional AChEI (IC50 = 0.21 μM, Ki = 0.19 μM) and displayed dual hMAO inhibitory activity (hMAO-A IC50 = 0.94 μM, Ki = 0.057 μM and hMAO-B IC50 = 3.81 μM, Ki = 0.48 μM). Compound 23a acted as a selective IMAO-B (IC50 = 0.63 μM, Ki = 0.34 μM) while still displaying hChE inhibitory and bifunctional activity in the low micromolar range. Overall, these two compounds stand out as reversible multi-target inhibitors with favourable permeability, toxicological and drug-like profiles, thus being valid candidates for subsequent optimization and pre-clinical studies.

Chromone and donepezil hybrids as new multipotent cholinesterase and monoamine oxidase inhibitors for the potential treatment of Alzheimer's disease

A series of chromone and donepezil hybrids were designed, synthesized, and evaluated as multipotent cholinesterase (ChE) and monoamine oxidase (MAO) inhibitors for the potential therapy of Alzheimer's disease (AD). In vitro studies showed that the great majority of these compounds exhibited potent inhibitory activity toward BuChE and AChE and clearly selective inhibition for hMAO-B. In particular, compound 5c presented the most balanced potential for ChE inhibition (BuChE: IC50 = 5.24 μM; AChE: IC50 = 0.37 μM) and hMAO-B selectivity (IC50 = 0.272 μM, SI = 247). Molecular modeling and kinetic studies suggested that 5c was a mixed-type inhibitor, binding simultaneously to peripheral and active sites of AChE. It was also a competitive inhibitor, which occupied the substrate and entrance cavities of MAO-B. Moreover, compound 5c could penetrate the blood-brain barrier (BBB) and showed low toxicity to rat pheochromocytoma (PC12) cells. Altogether, these results indicated that compound 5c might be a hopeful multitarget drug candidate with possible impact on Alzheimer's disease therapy.

Kinetics and mechanism of hydrogen peroxide oxidation of chromone-3-carboxaldehydes in aqueous acid and micellar media

Oxidation of chromone-3-carboxaldehyde (CCA) and substituted analogues by H2O2 has been carried out in aqueous acid (HCl and H2SO4) and micellar media. Reaction kinetics indicated order in |CCA| as well as |H2O2| to be unity while it is a fraction (1 > n > O) in |acid|. Reaction rates were found to be faster in the solvents of low-dielectric constant (D). Added salt (KCl or (NH4)2SO4) increased the rate of oxidation marginally. On the basis of observed linearity of Amis plot and marginal positive salt effect, protonated CCA (enol form of CCA, a cation) and H2O2 (neutral molecule) were considered as reactive species in the rate limiting step. Reaction rates were found to be enhanced significantly in anionic and nonionic micellar (sodium dodecylsulfate (SDS) and Triton X-100 (Tx), respectively) media. However, cationic micelles [cetyl trimethyl ammonium bromide (CTAB)| indicated marginal retardation effect. Effect of anionic and cationic micelles has been interpreted in terms of electrostatic interactions, while that of nonionic micelles in terms of hydrophobic interactions. Structure-reactivity correlations have been interpreted by Hammett's equation. Negative "p" (reaction constant) values indicated cationic transition state. 1996 John Wiley &Sons, Inc.