52817-12-6

Usage

Uses

Used in Pharmaceutical Research:
6-Bromo-3-formylchromone is used as a reagent in the study of multidrug resistance reversal by some 3-formylchromones in human colon cancer and mouse lymphoma cells transfected with the human MDR1 gene. Its application in this field is due to its potential to help overcome resistance to certain medications, which is a significant challenge in cancer treatment.
Used in Chemical Synthesis:
6-Bromo-3-formylchromone is used as a starting material or intermediate in the preparation of chromone-containing sulfonamides. These compounds have potential applications in the development of new drugs, particularly in the field of antibiotics and other therapeutic agents.

InChI:InChI=1/C10H5BrO3/c11-7-1-2-8-9(3-7)14-5-6(4-12)10(8)13/h1-5H

Upstream product

• 1450-75-5 5-Bromo-2-hydroxyacetophenone 
• 68-12-2 N,N-dimethyl-formamide 
• 106-41-2 4-bromo-phenol 
• 1761-61-1 5-bromosalicyclaldehyde 
• 1927-95-3 4-bromophenyl acetate 

Downstream Products

• 68827-57-6 6-bromo-3-(4,5-diphenyl-1H-imidazol-2-yl)-chromen-4-one 
• 95664-49-6 (2-Amino-pyrimidin-5-yl)-(5-bromo-2-hydroxy-phenyl)-methanone 
• 114646-72-9 7-(5'-bromo-2'-hydroxybenzoyl)-3-phenyl-1,2,4-triazolo<3,4-b><1,3,4>thiadiazepine 
• 80472-50-0 1-[5-(5-Bromo-2-hydroxy-benzoyl)-2-methyl-pyridin-3-yl]-ethanone 
• 51085-91-7 6-bromo-4-oxo-4H-chromene-3-carboxylic acid 
• 68287-72-9 (5-bromo-2-hydroxyphenyl)(1-phenyl-1H-pyrazol-4-yl)methanone 

Relevant academic research and scientific papers

Synthesis of Chromeno[2,3-d]pyrimidin-5-one Derivatives from 1,3,5-Triazinanes via Two Different Reaction Pathways

1,3,5-Triazinanes, as a kind of versatile building block, are applied in the synthesis of chromeno[2,3-d]pyrimidin-5-one derivatives via two different reaction modes, which perfectly exhibits the powerful function of 1,3,5-triazinane as a three-atom synth

Chromone dioxadiazole compound as well as preparation method and application thereof

The preparation method comprises the following steps: adding an intermediate F and bis (acetoxy) iodobenzene to dichloromethane for reaction to obtain the chromone compound. The invention provides a novel chromone dioxadiazole compound and a preparation method thereof, and overcomes the defects of large toxicity and high preparation cost of the traditional method.

Synthesis and biological evaluation of chromone-3-carboxamides

The aim of our study was to synthesize novel chromone-3-carboxamides and to conduct biological evaluations in search for lead compounds for the treatment of a range of debilitating disease states. Corresponding 2-hydroxyacetophenones were subjected to Vilsmeier-Haack formylation to give chromone-3-carbaldehydes, which were subsequently oxidised to give chromone-3-carboxylic acids. Treatment of the carboxylic acids with thionyl chloride resulted in the in situ formation of the corresponding acid chlorides, which were reacted with various amines in the presence of triethylamine to give the corresponding novel chromone-3-carboxamides in good yields. Selected chromone derivatives were then evaluated for their anti-inflammatory, anti-tryponosomal and cytotoxic properties.

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.

NHC-Catalyzed Cascade Reaction between β-Methyl Enals and Dienones for Quick Construction of Complex Multicyclic Lactones

A NHC-promoted cascade reaction between β-methyl enal and dienone is developed for quick access to multicyclic lactone molecules bearing quaternary chiral carbon centers. Our study constitutes the first 1,6-addition of the acylazolium vinyl enolate γ-carbon via NHC catalysis and provides rapid access to complex lactone molecules that are otherwise difficult to prepare. The structurally sophisticated lactone products bearing up to four fused ring structures are afforded in up to quantitative yields with good to excellent enantioselectivities.

Organocatalytic [10+4] cycloadditions for the synthesis of functionalised benzo[a]azulenes

A direct and mild strategy for the synthesis of benzo[a]azulenes based on an organocatalytic [10+4] cycloaddition reaction is described. The strategy enables a diversity-oriented approach for the synthesis of various poly-functionalised azulenes from easily accessible starting materials.

One pot and metal-free approach to 3-(2-Hydroxybenzoyl)-1-aza-anthraquinones

Herein, a direct strategy to synthesize 3-(2-hydroxybenzoyl)-1-aza-anthraquinones with excellent efficiency,mild conditions, and benign functional group compatibilitywas reported. Avariety of 3-formylchromone compounds were employed as compatible substrates and this protocol gave the 3-(2-hydroxybenzoyl)-1-aza-anthraquinone derivatives in good to excellent yields without inert gas and expensive transition metal catalysts. Some compounds displayed good anti-proliferative activities.

Synthesis and Antimicrobial Activity of (Z)-3-{[3-Oxobenzofuran-2(3H)-ylidene]methyl}-4H-chromen-4-one Derivatives

A series of (Z)-3-{[3-oxobenzofuran-2(3H)-ylidene]methyl}-4H-chromen-4-one derivatives have been synthesized from 2-hydroxyl acetophenones by the Vilesmeier–Haack reaction, Claisen–Schmidt reaction and mercury(II) acetate/cupric bromide. All the synthesized compounds were characterized by IR, 1H and 13C NMR, and mass spectral data and elemental analysis. The products were tested for their in vitro antimicrobial activity.

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.