29310-88-1

Usage

Uses

Used in Chemical Synthesis:
(3-BROMOACETYL)COUMARIN is used as a chemical intermediate for the synthesis of various compounds, including:
1. 3-(bromoacetyl)coumarin oxime, which is produced by reacting (3-BROMOACETYL)COUMARIN with hydroxylamine hydrochloride in methanol.
2. 3-(bromoacetyl)coumarin-O-methyloxime, which is synthesized by reacting (3-BROMOACETYL)COUMARIN with O-benzylhydroxylammonium chloride and diluted HCl in methanol.
3. 3-(bromoacetyl)coumarin-O-benzyloxime, which is obtained by reacting (3-BROMOACETYL)COUMARIN with O-benzyl hydroxylamine hydrochloride in methanol.
4. 3-[2′-(2′′-arylidenehydrazinyl)thiazolyl]coumarins, which are synthesized by reacting (3-BROMOACETYL)COUMARIN with benzaldehyde thiosemicarbazones.
These synthesized compounds can be further utilized in different industries, such as pharmaceuticals, materials science, and chemical research, for various applications like drug development, molecular probes, and advanced materials.

InChI:InChI=1/C11H7BrO3/c12-6-9(13)8-5-7-3-1-2-4-10(7)15-11(8)14/h1-5H,6H2

Upstream product

• 3949-36-8 3-acetylcoumarin 
• 219506-41-9 Phosphoric acid dimethyl ester 1-(2-oxo-2H-chromen-3-yl)-vinyl ester 
• 90-02-8 salicylaldehyde 

Downstream Products

• 33856-06-3 3?(2?(4?tolylamino)thiazol?4?yl)?2H?chromen?2?one 
• 34560-08-2 3-[2-(4-ethoxy-anilino)-thiazol-4-yl]-chromen-2-one 
• 33856-04-1 3?(2?((4?bromophenyl)amino)thiazol?4?yl)?2H?chromen?2?one 
• 33856-05-2 3?(2?((4?nitrophenyl)amino)thiazol?4?yl)?2H?chromen?2?one 
• 33856-07-4 3?(2?((4?methoxyphenyl)amino)thiazol?4?yl)?2H?chromen?2?one 
• 33856-02-9 3?(2?(phenylamino)thiazol?4?yl)?2H?chromen?2?one 
• 33856-03-0 3?(2?((4?chlorophenyl)amino)thiazol?4?yl)?2H?chromen?2?one 
• 88735-49-3 3-(2-p-Tolyl-thiazol-4-yl)-chromen-2-one 
• 136497-20-6 5-(2-Oxo-2H-chromen-3-yl)-2-thioxo-2H-pyrrole-3-carbonitrile 
• 88735-45-9 2-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl)acetonitrile 
• 88735-50-6 3-[2-(3,4-dimethoxy-phenyl)-thiazol-4-yl]-chromen-2-one 
• 129545-40-0 3-[2-(2-Methoxy-phenylamino)-6H-[1,3,4]thiadiazin-5-yl]-chromen-2-one 
• 108222-57-7 3-[3-(4-Nitro-phenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-6-yl]-chromen-2-one 
• 116317-09-0 3-{2-[3-(2-Hydroxy-phenyl)-5-phenyl-pyrazol-1-yl]-thiazol-4-yl}-chromen-2-one 

Relevant academic research and scientific papers

A new and efficient method for conjugate addition of trialkylphosphites to 3-acylsubstituted coumarins

A new and efficient conjugate addition of trialkylphosphites to 3-ω-bromoacetylcoumarin 1 catalysed by p-toluenesulfonic acid (TsOH) has been studied. Under the same conditions, an enolphosphate gave the corresponding esters of 3-acetyl-4-phosphono-2-oxochromans in high yields. The use of TsOH in the reaction of 3-acetyl-, 3-benzoyl-, and 3-ethoxycarbonyl coumarins led mainly to 1,4-addition products - the corresponding 3-acyl-4-dialkylphosphono-2- oxochromans - in very good yields. Graphical Abstract

An efficient synthesis of pyrrolo[2,1-a]isoquinoline derivatives containing coumarin skeletons via a one-pot, three-component reaction

New dialkyl 3-(2-oxo-2H-3-chromenylcarbonyl)pyrrolo[2,1-a]isoquinoline-1,2-dicarboxylate derivatives were prepared by the reaction of 3-(2-bromoacetyl)coumarins, isoquinoline, and dialkyl acetylenedicarboxylates in the presence of triethylamine. This protocol has some advantages such as easy purification, easy performance, and good yields. The structures were confirmed spectroscopically (IR, 1H- and 13C-NMR, and EI-MS) and by elemental analyses. A plausible mechanism for this reaction is proposed (Scheme 2).

Tetrabutylammonium tribromide: An effective green reagent for the one-pot reaction of 3-acetyl-2H-chromen-2-ones with o-phenylenediamines

An efficient and completely greener approach has been outlined for the reaction of 3-acetyl-2H-chromen-2-ones with o-phenylenediamines using tetrabutylammonium tribromide (TBATB) to obtain 3-(quinoxalin-2-yl)-2H-chromen-2-ones in one-pot. Alternatively, a step-wise method has also been demonstrated for the synthesis of 3-(quinoxalin-2-yl)-2H-chromen-2-ones, where 3-acetyl-2H-chromen-2-ones has first treated with TBATB to give 3-(2-bromoacetyl)-2H-chromen-2-one followed by its nucleophilic substitution reaction with o-phenylenediamines. Use of polyethylene glycol-600 (PEG-600) as the solvent media, mild reaction conditions and easy isolation procedure of products are the added advantages for this synthesis. Both the one-pot and step-wise methods have been compared in terms of their reaction yields and one-pot synthesis was found to be superior. All the synthesized compounds were confirmed by characterization with 1HNMR, 13CNMR, HRMS, IR spectroscopy.

Synthesis and potent antimicrobial activity of novel coumarylthiazole α-aminophosphonates derivatives

Abstract: Herein, we reported a novel series of?α-aminophosphonates derivatives (IV)a–m bearing an important pharmacophore coumarylthiazole moiety. All the new compounds have been synthesized?via?Kabachnik–Fields reaction under ultrasonic irradiation. The products were obtained in good yield with a simple workup and were confirmed using various spectroscopic methods. All these compounds (IV)a–m were screened for their in vitro for antimicrobial activity against thirteen Gram-negative bacteria and five Gram-positive bacteria and Candida albicans strains. The results showed that all the synthesized compounds exhibited moderate antibacterial activities against both references and multidrug-resistant and antifungal strains. The compound?(IV)e?showed the highest activities against all pathogens of the tested microbial strains with?MIC of 0.125?μg/mL.?The compounds (IV)h, (IV)f, (IV)b, and (IV)d exhibited moderate and promising activities with MIC of 0.125?μg/mL. Structure–activity relationship revealed that inhibitory activity of the synthesized compounds is related to the type of the substituted group on phenyl rings, and these results showed that the electron-donating groups at?ortho?and?para?positions have a high relationship increasing antimicrobial activities than the electron‐withdrawing groups. These results confirm that coumarylthiazole α-aminophosphonates compounds can be potential antimicrobial drugs candidate. Graphic abstract: [Figure not available: see fulltext.].

DFT-based molecular modeling, NBO analysis and vibrational spectroscopic study of 3-(bromoacetyl)coumarin

The NIR-FT Raman and FT-IR spectra of 3-(bromoacetyl)coumarin (BAC) molecule have been recorded and analyzed. Density functional theory (DFT) calculation of two BAC conformers has been performed to find the optimized structures and computed vibrational wavenumbers of the most stable one. The obtained vibrational wavenumbers and optimized geometric parameters were seen to be in good agreement with the experimental data. Characteristic vibrational bands of the pyrone ring and methylene and carbonyl groups have been identified. The lowering of HOMO-LUMO energy gap clearly explains the charge transfer interactions taking place within the molecule.

Synthesis and molecular docking studies of coumarinyl thiazole as cell division protein kinase 2 inhibitor

A series of 2-alkylamino-4-(3-coumarinyl)thiazoles were synthesized, characterized and evaluated their anticancer activity through molecular docking studies. Cell division protein kinase 2 (PDB code: 1KE9) is selected as a target and the compounds which obeys Lipinski rule of five is selected as a ligand. Molecular docking study is carried out using AutoDock Vina in PyRx virtual screening tool. This study revealed that all the compounds are active against the molecular target and compounds 5a and 5c have the highest docking score.

PEG-600 mediated one-pot reaction of 3-acetyl-2: H -chromen-2-one with heterylthiols and phenylthioureas using tetrabutylammonium tribromide as an efficient green reagent

A simple method for the one-pot reaction of 3-acetyl-2H-chromen-2-one with different heterylthiols and phenylthioureas under green conditions using tetrabutylammonium tribromide (TBATB) as an efficient reagent has been described. 3-Acetyl-2H-chromen-2-one

3-(5-(Benzylideneamino)thiazol-3-yl)-2H-chromen-2-ones: A new class of alkaline phosphatase and ecto-5′-nucleotidase inhibitors

A new series of 3-(2-(benzylideneamino)thiazol-4-yl)-2H-chromen-2-ones has been synthesized. The structures of the compounds were established by means of 1H and 13C NMR spectroscopy. All compounds were evaluated for their potential t

Design, synthesis and biological evaluation of novel coumarin thiazole derivatives as α-glucosidase inhibitors

A new series of coumarin thiazole derivatives 7a-7t were synthesized, characterized by 1H NMR, 13C NMR and element analysis, evaluated for their α-glucosidase inhibitory activity. The majority of the screened compounds displayed potent inhibitory activities with IC50 values in the range of 6.24 ± 0.07-81.69 ± 0.39 μM, when compared to the standard acarbose (IC50 = 43.26 ± 0.19 μM). Structure-activity relationship (SAR) studies suggest that the pattern of substitution in the phenyl ring is closely related to the biological activity of this class of compounds. Among all the tested molecules, compound 7e (IC50 = 6.24 ± 0.07 μM) was found to be the most active compound in the library of coumarin thiazole derivatives. Enzyme kinetic studies showed that compound 7e is a non-competitive inhibitor with a Ki of 6.86 μM. Furthermore, the binding interactions of compound 7e with the active site of α-glucosidase were confirmed through molecular docking. This study has identified a new class of potent α-glucosidase inhibitors for further investigation.

In vitro inhibition effects on erythrocyte carbonic anhydrase I and II and structure-activity relationships of cumarylthiazole derivatives

Coumarin and heterocyclic compounds incorporating urea have clinical applications as antiepileptics, diuretics, and antiglaucoma agents due to their carbonic anhydrase inhibitory properties. We investigated inhibition of carbonic anhydrase I and II with a series of coumarylthiazole derivatives containing urea/thiourea groups. All the investigated compounds exhibited inhibitory activity on both hCA I and hCA II, with 1-(3-chlorophenyl)-3-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl)urea being the strongest inhibitor. Structure–activity relationship study showed that most of urea derivatives were more inhibiting for hCA I and hCA II than thiourea derivatives. The electron-withdrawing groups at the phenyl ring increased the inhibitory activity compared to electron-donating groups.