3855-87-6

Usage

Uses

Used in Organic Synthesis:
6,8-DIBROMOCOUMARIN-3-CARBOXYLIC ACID is used as a building block for the synthesis of complex organic molecules, contributing to the development of new compounds with diverse applications in various industries.
Used in Medicinal Chemistry:
In the pharmaceutical industry, 6,8-DIBROMOCOUMARIN-3-CARBOXYLIC ACID is used as a precursor for the preparation of biologically active compounds, potentially leading to the discovery of new drugs with therapeutic benefits.
Used as a Fluorescent Probe:
6,8-DIBROMOCOUMARIN-3-CARBOXYLIC ACID is utilized as a fluorescent probe for detecting superoxide, an important reactive oxygen species involved in various biological processes and diseases. Its use in this capacity aids researchers in studying oxidative stress and related conditions.
Used for Antimicrobial and Antifungal Properties:
6,8-DIBROMOCOUMARIN-3-CARBOXYLIC ACID exhibits antimicrobial and antifungal properties, making it a valuable compound for use in the development of new antibiotics and antifungal agents to combat drug-resistant infections.
Used in Research and Development:
6,8-DIBROMOCOUMARIN-3-CARBOXYLIC ACID is employed in research settings to explore its potential applications and properties, furthering our understanding of its role in various chemical and biological processes.

InChI:InChI=1/C10H4Br2O4/c11-5-1-4-2-6(9(13)14)10(15)16-8(4)7(12)3-5/h1-3H,(H,13,14)/p-1

Upstream product

• 90-59-5 3,5-Dibromosalicylaldehyde 
• 141-82-2 malonic acid 
• 2199-89-5 6,8-dibromo-2-oxo-2H-1-benzopyran-3-carboxylic acid ethyl ester 
• 372-09-8 cyanoacetic acid 
• 2033-24-1 cycl-isopropylidene malonate 

Downstream Products

• 98994-86-6 6,8-dibromo-2-oxo-2H-chromene-3-carboxylic acid amide 
• 325807-61-2 6,8-dibromo-2-oxo-N-o-tolyl-2H-chromene-3-carboxamide 
• 325807-60-1 6,8-dibromo-N-(2-methoxyphenyl)-2-oxo-2H-chromene-3-carboxamide 
• 325807-62-3 6,8-dibromo-2-oxo-N-m-tolyl-2H-chromene-3-carboxamide 
• 955208-53-4 6,8-dibromo-2-oxo-N-(3-(trifluoromethyl)phenyl)-2H-chromene-3-carboxamide 
• 1611471-80-7 6,8-dibromo-2-oxo-N,N-diphenyl-2H-chromene-3-carboxamide 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of coumarin-based N-hydroxycinnamamide derivatives as novel histone deacetylase inhibitors with anticancer activities

A series of novel coumarin-based N-hydroxycinnamamide derivatives were designed and synthesized as histone deacetylase (HDAC) inhibitors. Most of the synthesized compounds showed potent HDAC inhibitory activity and significant antiproliferative activity a

3-substituted coumarin derivative and application and GPR35 receptor agonist

The invention discloses a 3-substituted coumarin derivative and a pharmaceutically acceptable salt, a solvate, a hydrate or a crystal form. The compound of the invention generally exhibits high agonistic activity against human G protein-coupled receptor 35 (GPR35) and is specific agonists of the human GPR35 receptor. The compound provided by the invention is an active ligand of the novel GPR35 receptor, and the compound and the pharmaceutically acceptable salt, the solvate, the hydrate or the crystal form thereof generally exhibit higher activity and good selectivity to the human GPR35. The 3-substituted coumarin derivative is the specific agonist of the GPR35 receptor and can be used in the preparation of a medicament for treating, preventing and inhibiting a disease mediated by the GPR35receptor.

Discovery of 2H-Chromen-2-one Derivatives as G Protein-Coupled Receptor-35 Agonists

A family of 2H-chromen-2-one derivatives were identified as G protein-coupled receptor-35 (GPR35) agonists using dynamic mass redistribution assays in HT-29 cells. The compounds with 1H-tetrazol-5-yl in 3-substituted position displayed higher potency than the corresponding carboxyl analogs, and the hydroxyl group in the 7-position also played an important role in GPR35 agonistic activity. 6-Bromo-7-hydroxy-8-nitro-3-(1H-tetrazol-5-yl)-2H-chromen-2-one (50) was found to be the most potent GPR35 agonist with an EC50 of 5.8 nM. Calculating the physicochemical properties of compounds with moderate to high potency suggested that compounds 30, 50, and 51 showed good druggability. This study provides a novel series of GPR35 agonists, and compound 50 may be a powerful tool to study GPR35.

Synthesis, evaluation and structure-activity relationship of new 3-carboxamide coumarins as FXIIa inhibitors

Inhibitors of the coagulation factor XIIa (FXIIa) are attractive to detail the roles of this protease in hemostasis and thrombosis, to suppress artifact due to contact pathway activation in blood coagulation assays, and they are promising as antithrombotic therapy. The 3-carboxamide coumarins have been previously described as small-molecular-weight FXIIa inhibitors. In this study, we report a structure-activity relationship (SAR) study around this scaffold with the aim to discover new selective FXIIa inhibitors with an improved physico-chemical profile. To better understand these SAR, docking experiments were undertaken. For this purpose, we built an original hybrid model of FXIIa. This model has the advantage to gather the best features from the recently published crystal structure of FXIIa in its zymogen form and a more classical homology model. Results with the hybrid model are encouraging as they help understanding the activity and selectivity of our best compounds.

Et3N catalyzed cascade reaction of Meldrum’s acid with ortho-hydroxyaryl aldehydes for the synthesis of coumarin-3-carboxylic acids under solvent-less condition

Abstract: The synthesis of coumarin-3-carboxylic acids in good yields is realized through a triethylamine catalyzed Knoevenagel-intramolecular cyclization tandem reaction of Meldrum’s acid with various ortho-hydroxyaryl aldehydes. This method expands the catalyst library about the synthesis of coumarin-3-carboxylic acids and also has advantages of using much less water as solvent, a cheap and eco-friendly catalyst, clean reaction conditions, simple workup procedure and easy isolation. Graphical Abstract: [Figure not available: see fulltext.]

New 2H-chromene-3-carboxamide derivatives: Design, synthesis and use as inhibitors of hMAO

A series new 2H-chromene-3-carboxamide derivatives 4a-4t were synthesized and evaluated as monoamine oxidase A and B (MAO-A and MAO-B) inhibitors. Among them, compound 4d (IC50 = 0.93 μM, IC50 iproniazid = 7.80 μM) showed the most ac

New coumarin derivatives: Design, synthesis and use as inhibitors of hMAO

A series new 2H-chromene-3-carboxamides (4a-4i) and S-2H-chromene-3- carbothioates (5j-5t) were synthesized and evaluated as monoamine oxidase A and B inhibitors. Among them, compound 5k (IC50 = 0.21 μM, IC 50 iproniazid = 7.65 μM) showed the most activity and higher MAO-B selectivity (189.2-fold vs 1-fold) with respect to the MAO-A isoform. The need to clarify at a 3D level some important molecular aspects of discussed SAR, we undertaked a number of docking simulations to better assess. The steric effect was analyzed interms of both posing and scoring by investigating the nature of the binding interactions. The docking results of active compound 5k with hMAO-B complex indicated that conserved residue ILE 199 was important for ligand binding via Sigma-Pi interaction.

Potassium phosphate catalyzed efficient synthesis of 3-carboxycoumarins

An efficient and rapid synthesis of 3-carboxycoumarins has been expediently accomplished by a reaction of salicylaldehyde with Meldrum's acid using potassium phosphate as an inexpensive catalyst at ambient temperature.

Synthesis and selective human monoamine oxidase inhibition of 3-carbonyl, 3-acyl, and 3-carboxyhydrazido coumarin derivatives

Several 3-carbonyl (1-26), 3-acyl (27-52), and 3-carboxyhydrazido (53-58) coumarins have been synthesized in high yields (72-99%) and tested in vitro for their human monoamine oxidase A and B (hMAO-A and hMAO-B) inhibitory activity. Different substituents on the coumarin nucleus were evaluated for their effect on biological activity and isoform selectivity. Substitution at position C7 of the 3-ethyl ester coumarin ring, or the introduction of a hydrazido substituent at C3, were important to obtain highly potent and selective hMAO-B inhibitors with IC50 values in the nanomolar range. Some derivatives were also submitted to a stability test and showed no chemical cleavage in vitro.

Synthesis, selective anti-Helicobacter pylori activity, and cytotoxicity of novel N-substituted-2-oxo-2H-1-benzopyran-3-carboxamides

N-substituted-3-carboxamido-coumarin derivatives were prepared and evaluated for selective antibacterial activity against 20 isolates of Helicobacter pylori clinical strains, including five metronidazole resistant ones. Some of them possessed the best activity against H. pylori metronidazole resistant strains with MIC values lower than the drug reference (metronidazole). Furthermore, anti-inflammatory activity through the inhibition of the IL-8 production was investigated.