2199-90-8

Usage

Uses

Used in Organic Synthesis:
ETHYL 6-BROMOCOUMARIN-3-CARBOXYLATE is used as a reagent in organic synthesis for the preparation of various chemical compounds. Its unique structure and properties make it a useful building block in the synthesis of complex organic molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, ETHYL 6-BROMOCOUMARIN-3-CARBOXYLATE is used as a starting material for the development of novel drugs and pharmaceuticals. Its fluorescent properties allow for the detection and analysis of various compounds, aiding in the discovery of new therapeutic agents.
Used in Fluorescent Dyes and Indicators Production:
ETHYL 6-BROMOCOUMARIN-3-CARBOXYLATE is used as a key component in the production of fluorescent dyes and indicators. Its fluorescent properties make it suitable for applications in various fields, such as bioimaging, diagnostics, and environmental monitoring.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, ETHYL 6-BROMOCOUMARIN-3-CARBOXYLATE is employed for the development of new drugs and pharmaceuticals. Its versatile properties and applications in various fields make it a valuable tool for researchers working on drug discovery and development.

InChI:InChI=1/C12H9BrO4/c1-2-16-11(14)9-6-7-5-8(13)3-4-10(7)17-12(9)15/h3-6H,2H2,1H3

Upstream product

• 105-53-3 diethyl malonate 
• 1761-61-1 5-bromosalicyclaldehyde 
• 105-56-6 ethyl 2-cyanoacetate 
• 64-17-5 ethanol 
• 107-91-5 cyanoacetic acid amide 
• 2033-24-1 cycl-isopropylidene malonate 
• 3702-98-5 ethyl 4,4,4-trichloroacetoacetate 
• 2316-64-5 5-bromo-2-hydroxybenzyl alcohol 
• 106-41-2 4-bromo-phenol 
• 623-47-2 propynoic acid ethyl ester 
• 90-02-8 salicylaldehyde 

Downstream Products

• 2199-87-3 6-bromocoumarin-3-carboxylic acid 
• 76693-35-1 2-oxo-6-bromo-2H-chromene-3-carbonitrile 
• 1173095-67-4 6-bromo-2-oxo-2H-chromene-3-carbohydrazide 
• 81309-22-0 C₁₉H₁₄BrNO₅ 
• 312756-47-1 C₁₇H₁₀BrNO₅ 
• 2199-94-2 6-bromo-2-oxo-2H-1-benzopyran-3-carboxylic acid chloride 
• 38485-82-4 N-phenyl-6-bromo-2-oxo-2H-1-benzopyran-3-carboxamide 
• 312616-85-6 6-bromo-3-(2-hydroxy-phenylaminocarbonyl)coumarin 
• 1448675-28-2 6-bromo-3-ethoxycarbonyl-4-(4-methoxyphenoxymethyl)-3,4-dihydrocoumarin 

Relevant academic research and scientific papers

Facile Synthesis and Anticancer Activity Study of Novel Series of Substituted and Fused Coumarin Derivatives

Various new substituted and fused coumarin analogues have been synthesized via different synthetic pathways. Among which are variable substituted coumarin derivatives bearing either biologically active side chains or rings at 5, 6, and 3 positions of the coumarin nucleus as indicated in compounds 10, 12, 13, 16–19, 21, 23–32, 38, and 42–45. In addition, different pyranocoumarin derivatives either substituted as in compounds 2, 3, and 6 or fused as compounds 33–36, pyranoxanthene analogues such as compounds 4 and 46, coumarinotriazolothiadiazine derivative 8, coumarinonaphthodiazocin analogue 39 and coumarinopyrazolone derivative 40 were synthesized. Thirty-eight of the synthesized compounds were subjected to in vitro anticancer screening against mammalian liver carcinoma HepG2 and breast carcinoma MCF7 cell lines using Cisplatin as a standard reference. The anticancer activity screening results revealed that, among the tested compounds, compounds 16, 40, and 43 bearing 4-chlorophenyl-2-aminopyridine-3-carbonitrile attached to C6 position, fused pyrazolone ring or attached to 4-chlorophenyl-2-oxo-dihydropyridine-3-carbonitrile at C3 position of the coumarin nucleus, respectively, exhibited moderate to strong activity against both cell lines.

Synthesis, crystal structure, spectroscopic characterization and anti-fungal activity of Ethyl 2-Oxo-2H-chromene-3-carboxylateDerivatives

Ethyl 2-oxo-2H-chromene-3-carboxylate derivatives were synthesized and characterized by FT-IR, NMR, MS and X-ray crystal diffraction. Compound 3d crystallizes in the triclinic system with space group P-1. Compound 3e crystallizes in the monoclinic system with space group P21/c. The potential anti-fungal activities have been studied against five kinds of common fungi at concentrations of 200 ppm and 500 ppm. The research showed that the target compounds exhibit certain anti-fungal activity against the tested fungal strains. The inhibition rate of compound 3b was the highest against Fusarium oxysporum, up to 60.29% at 500 ppm. Compound 3b is promising to become the lead compound of pesticide in the future, which is worthy of further study.

Synthesis, characterization and antioxidant activity studies of new coumarin tethered 1,3,4-oxadiazole analogues

The present work describes the synthesis of a series of substituted 3-(5-phenyl-1,3,4-oxadiazol-2-yl)-2H-chromen-2-ones 7(a–j) using substituted aldehydes with analogues of hydrazine hydrates by grinding technique in the presence of Iodine which helps in the cyclization process. The structures of the synthesized compounds were elucidated by spectroscopic techniques such as IR, 1H NMR, 13C NMR, and LCMS. The comparative antioxidant property (using DPPH and hydroxyl radical scavenging) has been studied with the synthesized compounds 7(a-j) and the standards. Compounds 7d and 7i show the prominent radical scavenging activity. Graphic abstract: [Figure not available: see fulltext.] Synopsis: Series of ten new coumarin-oxadiazole hybrids synthesized in three steps starting from salicylaldehyde and diethylmalonate. All new compounds were spectroscopically characterized. The results of radical scavenging activities show that, two compounds of the series 7d and 7i displayed potent DPPH and hydroxyl radical activity comparable to the standards employed, and therefore acts as antioxidant leads.

Coumarin derivatives act as novel inhibitors of human dipeptidyl peptidase III: Combined in vitro and in silico study

Dipeptidyl peptidase III (DPP III), a zinc-dependent exopeptidase, is a member of the metalloproteinase family M49 with distribution detected in almost all forms of life. Although the physiological role of human DPP III (hDPP III) is not yet fully elucida

An efficient synthesis of some new coumarin hybrids endowed with expected biological activity

Reactions of 5-bromo-2-hydroxybenzaldehyde with cyanoacetic acid hydrazide derivatives in refluxing ethanol afforded some new chromene-based polyfunctionally substituted heteroaromatics. The antimicrobial activity of some of the obtained products was eval

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.

Supramolecular synthesis of coumarin derivatives catalyzed by a coordination-assembled cage in aqueous solution

A self-assembled Pd4L2 cage is employed as a water-soluble molecular flask for the synthesis of functionalized coumarins from a series of salicylaldehyde derivatives and cyanoacetates/malononitrile. The catalytic reaction features mild aqueous conditions and broad substrate scope. Crystal structures of the host-guest complexes for two substrates and one analogous intermediate have been obtained, shedding light on the supramolecular reaction mechanism. Michaelis-Menten kinetic studies were performed in one typical case, revealing that the rate of product formation has been enhanced by over 23-fold in contrast to the background reaction without cage. Moreover, the same reaction catalyzed by a smaller Pd6L4 cage gives a mixture of products and much lower yields, suggesting that fine-tuning on the size and symmetry of the cages’ cavity is crucial for their applications in supramolecular catalysis.

Solvent-Free FeCl3-Assisted Electrophilic Fluorine-Catalyzed Knoevenagel Condensation to Yield α,β-Unsaturated Dicarbonyl Compounds and Coumarins

A highly environmentally friendly procedure was developed for the Knoevenagel condensation of aromatic aldehydes with diethyl malonate in the presence of FeCl3 and N-fluorobenzenesulfonimide as a source of electrophilic fluorine under solvent-free conditions. The scope of the reaction was explored using commercially available substrates. The reaction with substituted salicylaldehydes afforded the corresponding coumarin derivatives which attract interest due to their potential medicinal importance.