2199-87-3

Usage

Uses

Used in Pharmaceutical Industry:
6-Bromocoumarin-3-carboxylic acid is used as a therapeutic agent for the treatment of various neurological conditions. Its interaction with NMDA receptor subtypes Glu1/Glu2 allows for the modulation of these receptors, which can be beneficial in managing a range of neurological disorders.
Used in Neurological Treatments:
6-Bromocoumarin-3-carboxylic acid is used as a neuromodulator for the inhibition of NMDA receptor subtypes Glu1/Glu2. This inhibition can be employed in therapeutic treatments aimed at alleviating symptoms and improving the quality of life for patients suffering from neurological conditions.

Synthesis Reference(s)

Synthetic Communications, 18, p. 717, 1988 DOI: 10.1080/00397918808077361

InChI:InChI=1/C10H5BrO4/c11-6-1-2-8-5(3-6)4-7(9(12)13)10(14)15-8/h1-4H,(H,12,13)/p-1

Upstream product

• 76693-35-1 2-oxo-6-bromo-2H-chromene-3-carbonitrile 
• 141-82-2 malonic acid 
• 1761-61-1 5-bromosalicyclaldehyde 
• 2033-24-1 cycl-isopropylidene malonate 
• 25016-01-7 5-bromo-2-methoxybenzaldehyde 
• 82486-43-9 2-hydroxy-5-bromobenzaldehyde oxime 
• 89-55-4 5-bromosalicyclic acid 
• 106-41-2 4-bromo-phenol 
• 22532-62-3 4-bromosalicylaldehyde 
• 90-02-8 salicylaldehyde 
• 117646-13-6 5-(5-Bromo-2-methoxy-benzylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione 
• 89228-64-8 6-bromo-N-hydroxy-2-oxo-2H-1-benzopyran-3-carboxamide 
• 2199-90-8 ethyl 6-bromo-2-oxo-2H-chromene-3-carboxylate 

Downstream Products

• 2199-94-2 6-bromo-2-oxo-2H-1-benzopyran-3-carboxylic acid chloride 
• 81309-22-0 C₁₉H₁₄BrNO₅ 
• 312756-47-1 C₁₇H₁₀BrNO₅ 
• 892298-52-1 6-bromo-3-(3-phenyl-1,2,4-oxadiazol-5-yl)coumarin 
• 892296-25-2 6-bromo-3-[3-(4-methoxyphenyl)-1,2,4-oxadiazol-5-yl]coumarin 
• 1569352-20-0 6-bromo-N-(4-chlorophenyl)-N-(2-(cyclohexylamino)-1-(2-((1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-2-oxoethyl)-2-oxo-2H-chromene-3-carboxamide 
• 1569352-21-1 6-bromo-N-(2-(cyclohexylamino)-1-(2-((1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-2-oxoethyl)-N-(4-methoxyphenyl)-2-oxo-2H-chromene-3-carboxamide 
• 1569352-22-2 N-(1-(2-((1-benzyl-1H-1,2,3-triazol-4-yl)methoxy)-5-nitrophenyl)-2-(cyclohexylamino)-2-oxoethyl)-6-bromo-2-oxo-N-phenyl-2H-chromene-3-carboxamide 
• 1569352-23-3 6-bromo-N-(2-(cyclohexylamino)-1-(5-methoxy-2-((1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-2-oxoethyl)-2-oxo-N-(p-tolyl)-2H-chromene-3-carboxamide 
• 1569352-12-0 N-(1-(2-((1-benzyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-2-(cyclohexylamino)-2-oxoethyl)-6-bromo-2-oxo-N-phenyl-2H-chromene-3-carboxamide 
• 1569352-13-1 6-bromo-N-(2-(cyclohexylamino)-1-(2-((1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-2-oxoethyl)-2-oxo-N-phenyl-2H-chromene-3-carboxamide 

Relevant academic research and scientific papers

A Primary Amide-Functionalized Heterogeneous Catalyst for the Synthesis of Coumarin-3-carboxylic Acids via a Tandem Reaction

A crystalline primary amide-based bifunctional heterogeneous catalyst, {[Cd2(2-BPXG)(Fum)2(H2O)2]·2H2O}n (1) (where, 2-BPXG = 2,2′-((1,4-phenylenebis(methylene))bis((pyridin-2-ylmethyl)azanediyl)) diacetamide and Fum = fumarate), has been developed for the one-pot synthesis of a series of potentially biologically active coumarin-3-carboxylic acids at room temperature via a Knoevenagel-intramolecular cyclization tandem reaction. Catalyst 1 is prepared at room temperature from a one-pot self-assembly process in 81% yield and high purity within a few hours and has a ladder-like polymeric architecture based on single-crystal X-ray diffraction. Additional characterization of 1 includes elemental analysis, infrared spectroscopy, thermogravimetric analysis, and powder X-ray diffraction. Based on the optimized conditions, it is determined that 1 is highly efficient (conditions: 2 mol % catalyst, 3 h, and 26-28 °C in methanol) for this reaction. Its recyclability up to five cycles without significant loss of activity and structural integrity is also demonstrated. Using both electron-donating and electron-withdrawing substituents on the salicylaldehyde substrate, seven different derivatives of coumarin-3-carboxylic acid were made. Additionally, the monoamine oxidase (MAO) inhibitor, coumarin-3-phenylcarboxamide, has also been synthesized from coumarin-3-carboxylic acid obtained in the catalysis process. A detailed mechanism of action is also provided.

Design, Synthesis, and Cholinesterase Inhibition Assay of Coumarin-3-carboxamide-N-morpholine Hybrids as New Anti-Alzheimer Agents

A new series of coumarin-3-carboxamide-N-morpholine hybrids 5a–5l was designed and synthesized as cholinesterases inhibitors. The synthetic approach for title compounds was started from the reaction between 2-hydroxybenzaldehyde derivatives and Meldrum's acid to afford corresponding coumarin-3-carboxylic acids. Then, amidation of the latter compounds with 2-morpholinoethylamine or N-(3-aminopropyl)morpholine led to the formation of the compounds 5a–5l. The in vitro inhibition screen against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) revealed that most of the synthesized compounds had potent AChE inhibitory while their BuChE inhibitions are moderate to weak. Among them, propylmorpholine derivative 5g (N-[3-(morpholin-4-yl)propyl]-2-oxo-2H-chromene-3-carboxamide) bearing an unsubstituted coumarin moiety and ethylmorpholine derivative 5d (6-bromo-N-[2-(morpholin-4-yl)ethyl]-2-oxo-2H-chromene-3-carboxamide) bearing a 6-bromocoumarin moiety showed the most activity against AChE and BuChE, respectively. The inhibitory activity of compound 5g against AChE was 1.78 times more than that of rivastigmine and anti-BuChE activity of compound 5d is approximately same as rivastigmine. Kinetic and docking studies confirmed the dual binding site ability of compound 5g to inhibit AChE.

Monoamine oxidase A and B inhibitory activities of 3,5-diphenyl-1,2,4-triazole substituted [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives

Monoamine oxidase (EC 1.4.3.4, MAO) is a flavin adenine dinucleotide-containing flavoenzyme located on the outer mitochondrial membrane and catalyzes the oxidative deamination of monoaminergic neurotransmitters and dietary amines. MAO exists in humans as two isoenzymes, hMAO-A and hMAO-B, which are distinguished by their tertiary structures, preferred substrates and inhibitors, and selective inhibition of these isoenzymes are used in the treatment of different diseases such as Alzheimer's, Parkinson's and depression. In the present study, we report the design, synthesis and characterization of 3,5-diphenyl-1,2,4-triazole substituted [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives as novel and selective inhibitors of hMAO-B. Twenty one compounds (38, 39a-h, 41a-d, 42a-h) were screened for their inhibitory activity against hMAO-A and hMAO-B by using in vitro Amplex Red reagent based fluorometric method and all compounds were found to be as selective h-MAO-B inhibitors to a different degree. The compound 42e and 42h displayed the highest inhibitory activity against hMAO-B with IC50 values of 2.51 and 2.81 μM, respectively, and more than 25-fold selectivity towards inhibition of hMAO-B. A further kinetic evaluation of the most potent derivative (42e) was also performed and a mixed mode of inhibition of hMAO-B by the compound 42e was determined (Ki = 0,26 μM). According to our findings the [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole emerged as a promising scaffold for the development of novel and selective hMAO-B inhibitors.

Synthesis of xanthene and coumarin derivatives in water by using β-Cyclodextrin

Simple and green procedure was developed for the synthesis of various xanthene and coumarin derivatives using beta-cyclodextrin (β-CD) as reusable catalyst at 70?°C in water. Condensation of salicylaldehyde (1?mmol) and dimedone (2?mmol) or 1,3 cyclohexadione (2?mmol) gave corresponding xanthene derivatives, while condensation of salicylaldehyde (1?mmol) with Meldrum’s acid (1?mmol) or 4-Hydroxy-6-methyl-2H-pyran-2-one (1?mmol) gave respective coumarin derivatives in impressive yields. Involvement of β-CD as catalyst was ascertained by inclusion complex evaluation of β-CD-salicylaldehyde with 1H NMR analysis at 70?°C. Graphic abstract: [Figure not available: see fulltext.].

Synthesis and biological evaluation of some 1,3-benzoxazol-2(3H)-one hybrid molecules as potential antioxidant and urease inhibitors

A new series of 1,3-benzoxazol-2(3H)-one hybrid compounds, including coumarin, isatin 1,3,4-triazole and 1,3,4-thiadiazole moieties, were synthesized and biologically evaluated for their antioxidant capacities and anti-urease properties. The synthesized benzoxazole-coumarin (6a–e) and benzoxazole-isatin (10a–c) hybrids showed remarkable urease inhibitory activities with IC50 (μM), ranging from 0.0306 ± 0.0030 to 0.0402 ± 0.0030, while IC50 of standard thiourea is 0.5027 ± 0.0293. The synthesized benzoxazole-triazole (8a–c) and benzoxazole-thiadiazole (9a–c) hybrids showed similar urease inhibitory activities with IC50 (μM), ranging from 0.3861 ± 0.0379 to 0.5126 ± 0.0345. The antioxidant activity of the synthesized compounds was evaluated for their antioxidant activities, such as reducing power and ABTS (2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) diammonium salt) radical scavenging. The results of ABTS radical scavenging activities of some of the synthesized molecules showed higher activities than standard Trolox, SC50 (μM) = 213.04 ± 18.12. One benzoxazole-coumarin (6f), two benzoxazole-isothiocyanate (7b, 7c), and two benzoxazole-triazole (8b, 8c) derivatives showed higher activities (SC50 (μM) values, 82.07 ± 10.34, 120.19 ± 7.30, 104.58 ± 10.55, 153.26 ± 7.14, and 144.82 ± 10.68, respectively) than standard Trolox, (SC50 (μM) = 213.04 ± 18.12).

Method for synthesizing coumarin-3-carboxylic acid compounds by one-pot two-step method

The invention relates to a method for synthesizing coumarin-3-carboxylic acid compounds by a one-pot two-step method. The structural formula of the coumarin-3-carboxylic acid compounds is shown in the description, wherein R1 is H , Cl , Br, NO2 , CH3 and HO . According to the synthesis process of the coumarin-3-carboxylic acid compounds, malonic acid, acetone and substituted salicylaldehyde serve as raw materials, iodine serves as a catalyst, acetic anhydride serves as a solvent, a series of coumarin-3-carboxylic acid compounds are synthesized through a one-pot cascade reaction, and the efficiency and the yield are greatly improved compared with a fractional step method.

Green synthesis method of coumarin-3-carboxylic acid compound

The invention relates to a green synthesis method of a coumarin-3-carboxylic acid compound. The synthesis process of the coumarin-3-carboxylic acid compound is as follows: R1 is H, Cl, Br, NO2, CH3 and HO. A series of coumarin-3-carboxylic acid compounds are synthesized in one step without a catalyst by taking R1-substituted salicylaldehyde and Meldrum's acid as raw materials and water as a reaction medium, the process steps are simple, the method has universality, reaction liquid can be repeatedly added for reaction, no waste or waste liquid is generated, the yield of a target product is greater than 54.3%, and the method is an environment-friendly green synthesis method.

Zirconium(IV) oxychloride: A simple and efficient catalyst for the synthesis of chromen-2-one derivatives

The present work explores a highly efficient, environmental friendly, green protocol for the synthesis of chromen-2-one derivatives (3a-m) by the condensation of salicylaldehydes with various active methylene compounds using zirconium (IV) oxychloride as catalyst. This is a convenient and rapid method for Knoevenagel condensation and this methodology offers several advantages including shorter reaction time, milder conditions, inexpensive catalyst, simple operational procedure and allowed to achieve the desired products in excellent yields. The structures of all the synthesized compounds were confirmed by spectral data.

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

Synthesis and biological evaluation of carvacrol-based derivatives as dual inhibitors of H. Pylori strains and ags cell proliferation

This study reports on the synthesis, structural assessment, microbiological screening against several strains of H. pylori and antiproliferative activity against human gastric adenocarcinoma (AGS) cells of a large series of carvacrol-based compounds. Structural analyses consisted of elemental analysis,1 H/13 C/19 F NMR spectra and crystallographic studies. The structure-activity relationships evidenced that among ether derivatives the substitution with specific electron-withdrawing groups (CF3 and NO2) especially in the para position of the benzyl ring led to an improvement of the antimicrobial activity, whereas electron-donating groups on the benzyl ring and ethereal alkyl chains were not tolerated with respect to the parent compound (MIC/MBC = 64/64 μg/mL). Ester derivatives (coumarin-carvacrol hybrids) displayed a slight enhancement of the inhibitory activity up to MIC values of 8–16 μg/mL. The most interesting compounds exhibiting the lowest MIC/MBC activity against H. pylori (among others, compounds 16 and 39 endowed with MIC/MBC values ranging between 2/2 to 32/32 μg/mL against all the evaluated strains) were also assayed for their ability to reduce AGS cell growth with respect to 5-Fluorouracil. Some derivatives can be regarded as new lead compounds able to reduce H. pylori growth and to counteract the proliferation of AGS cells, both contributing to the occurrence of gastric cancer.