106577-99-5

Basic information

• Product Name: 6-Chloro-3-(2-broMoacetyl)-2-chroMenone
• Synonyms: 6-Chloro-3-(2-broMoacetyl)-2-chroMenone;3-(2-bromoacetyl)-6-chloro-2H-1-benzopyran-2-one
• CAS NO: 106577-99-5
• Molecular Formula: C₁₁H₆BrClO₃
• Molecular Weight: 301.52054
• Mol File: 106577-99-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-Chloro-3-(2-broMoacetyl)-2-chroMenone(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Chloro-3-(2-broMoacetyl)-2-chroMenone(106577-99-5)
• EPA Substance Registry System: 6-Chloro-3-(2-broMoacetyl)-2-chroMenone(106577-99-5)

Safety Data

• Hazardous Substances Data: 106577-99-5(Hazardous Substances Data)

Usage

General Description

6-Chloro-3-(2-bromoacetyl)-2-chromenone is a chemical compound with the molecular formula C11H8O3ClBr. It is a derivative of 2-chromenone, a type of flavonoid found in certain plants. 6-Chloro-3-(2-broMoacetyl)-2-chroMenone is known for its potential antibacterial and antifungal properties, making it a possible candidate for use in pharmaceuticals and agricultural applications. Its structure contains a chloro and bromo functional group, which can potentially contribute to its biological activity. Further research and testing are needed to fully understand the potential uses and effects of 6-Chloro-3-(2-bromoacetyl)-2-chromenone.

Upstream product

• 635-93-8 5-chlorosalicyclaldehyde 
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• 53653-66-0 3-acetyl-6-chlorocoumarin 

Downstream Products

• 106578-09-0 6-Chloro-3-(2-phenyl-thiazol-4-yl)-chromen-2-one 
• 228854-68-0 propionic acid N'-[4-(6-chloro-2-oxo-2H-chromen-3-yl)-thiazol-2-yl]-hydrazide 
• 1190756-17-2 6-chloro-3-(2-(styrenesulfonyl)acetyl)-2H-2-chromen-2-one 
• 1190756-23-0 6-chloro-3-(2-(p-methylstyrenesulfonyl)acetyl)-2H-chromen-2-one 
• 1126640-67-2 3-[2-(p-tolylamino)thiazol-4-yl]-6-chloro-2H-chromen-2-one 
• 1233880-64-2 5-phenyl-3-[(6'-chloro-(3'-coumarinyl))]-7H-[1,3]-thiazolo-[3,2-a]-pyrimidine-7-one 
• 1264292-52-5 4-(4-(dimethylamino)benzylidene)-3-methyl-1-[4-(6-chloro-2-oxo-2H-chromen-3-yl)thiazol-2-yl]-1H-pyrazol-5(4H)-one 
• 1264292-58-1 4-(4-methoxybenzylidene)-3-methyl-1-[4-(6-chloro-2-oxo-2H-chromen-3-yl)thiazol-2-yl]-1H-pyrazol-5(4H)-one 
• 1430228-85-5 2-(3-(4-chlorophenyl)-5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazol-1-yl)-4-(6-chlorocoumarin-3-yl)thiazole 
• 1430228-89-9 2-(3-(4-bromophenyl)-5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazol-1-yl)-4-(6-chlorocoumarin-3-yl)thiazole 
• 1430228-93-5 2-(3-(4-fluorophenyl)-5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazol-1-yl)-4-(6-chlorocoumarin-3-yl)thiazole 
• 1558012-38-6 3-{(14E)-3-[2-(1H-indol-3-yl)ethyl]-2,3-dihydro-2-(phenylimino)thiazol-4-yl}-6-chloro-2H-chromen-2-one 
• 1558012-39-7 3-{(14E)-3-[2-(1H-indol-3-yl)ethyl]-2-(4-chlorophenylimino)-2,3-dihydrothiazol-4-yl}-6-chloro-2H-chromen-2-one 
• 1558012-40-0 3-{(14E)-3-[2-(1H-indol-3-yl)ethyl]-2-(p-tolylimino)-2,3-dihydrothiazol-4-yl}-6-chloro-2H-chromen-2-one 

Relevant articles and documents

Synthesis of Some 2-(3-Alkyl/aryl-5-trifluoromethylpyrazol-1-yl)-4-(coumarin-3-yl)thiazoles as novel antibacterial agents

Herein, we describe a one-pot synthesis of some novel 2-(3-alkyl/aryl-5-trifluoromethylpyrazol-1-yl)-4-(coumarin-3-yl)thiazoles (6) involving the reaction of 3-alkyl/aryl-5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazole-1-thiocarboxamides (3) with 3-bromoacetylcoumarins (5) in the presence of sodium carbonate in ethanol. Reaction of 3 with 5 in the absence of sodium carbonate, however, resulted in the formation of 2-(3-alkyl/aryl-5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazol-1-yl)-4-(coumarin-3-yl)thiazoles, which were subsequently dehydrated to 6 by refluxing in ethanol in the presence of sodium carbonate. The structure of the synthesized compounds (6) was confirmed by infrared (IR), mass, 1H NMR, and 13C NMR spectra and elemental analysis data. Newly synthesized compounds (6) showed moderate to good activity against Gram-positive bacteria.

One-pot multicomponent synthesis of indole incorporated thiazolylcoumarins and their antibacterial, anticancer and DNA cleavage studies

A series of indole incorporated thiazolylcoumarins (7a-q) have been synthesized and evaluated for their antibacterial, anticancer and DNA cleavage studies. Analysis of antibacterial studies indicated that all the synthesized compounds possess promising activity towards the screened bacterial strains. In vitro anticancerous action was studied for compound 7a (NSC: 768621/1) against the full panel of 60 human tumor cell lines. The five dose level activity results revealed that, the compound 7a was active against all the cell lines among them it has shown potent activity against Leukemia: CCRF-CEM (GI50: 0.33 μM), Non-Small Cell Lung Cancer: NCI-H522 (GI50: 1.03 μM), Colon Cancer: HCT-116 (GI50: 1.60 μM), CNS Cancer: SF-539 (GI50: 1.58 μM), Melanoma MALME-3M (GI50: 1.59 μM), Ovarian Cancer: OVCAR-3 (GI50: 1.16 μM), Renal Cancer: UO-31 (GI50: 0.76 μM), Prostate Cancer: PC-3 (GI50: 0.82 μM) and Breast Cancer: BT-549 (GI50: 1.13 μM). DNA cleavage studies revealed that even at 50 μg/mL concentration complete DNA digestion was observed for all the compounds, except for compound (7o) where partial DNA digestion was observed even at 100 μg/mL.

Synthesis and antimicrobial activity of some novel quinoline-pyrazoline-based coumarinyl thiazole derivatives

A series of novel 3-(2-(5-(2-chloroquinolin-3-yl)-3-substituted phenyl-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4-yl)-6-H/halo-2H-chromen-2-ones (9a–9y) was prepared as antimicrobial agents by the condensation of 3-(2-bromoacetyl)-6-H/halo-2H-chromen-2-ones (4

Synthesis and anti-acetylcholinesterase activities of novel glycosyl coumarylthiazole derivatives

Eleven glycosyl coumarylthiazole derivatives are synthesized by cyclization and condensation of glycosyl thiourea with 3-bromoacetyl coumarins in ethanol. The reaction conditions are optimized and good yields of products (80%–95%) are obtained. The structures of all new products were confirmed by IR, 1H and 13C NMR, and by HRMS (electrospray ionization). The in vitro acetylcholinesterase (AChE) inhibitory activities of these new compounds are tested by Ellman’s method. Among them, N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-4-(6-nitrocoumarinyl)-1,3-thiazole-2-amine showed the best activity with an in vitro AChE inhibitory rate of 58% and an IC50 value of 12 ± 0.38 μg/mL.

Design, synthesis, DFT, docking studies and ADME prediction of some new coumarinyl linked pyrazolylthiazoles: Potential standalone or adjuvant antimicrobial agents

The control of antimicrobial resistance (AMR) seems to have come to a dead end. The major consequences of the use and abuse of antibacterial drugs are the development of resistant strains due to genetic mutability of both pathogenic and nonpathogenic microorganisms. We, herein, report the synthesis, characterization and biological activities of coumarin-thiazole-pyrazole (CTP) molecular hybrids with an effort to explore and overcome the increasing antimicrobial resistance. The compounds were characterized by analyzing their IR, Mass, 1H and13C NMR spectral data and elemental analysis. The in vitro antimicrobial activity of the synthesized compounds was investigated against various pathogenic strains; the results obtained were further explained with the help of DFT and molecular orbital calculations. Compound 1b and 1f displayed good antimicrobial activity and synergistic effects when used with kanamycin and amphotericin B. Furthermore, in vitro cytotoxicity of compounds 1b and 1f were studied against HeLa cells (cervical cancer cell) and Hek-293 cells. The results of molecular docking study were used to better rationalize the action and prediction of the binding modes of these compounds.

Synthesis and pharmacological evaluation of some novel 2-(5-hydroxy-5- trifluoromethyl-4,5-dihydropyrazol-1-yl)-4-(coumarin-3-yl)thiazoles

A series of novel 2-(5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazol-1-yl)- 4-(coumarin-3-yl)thiazoles (6) were synthesized by condensing 3-(2-bromoacetyl)coumarins (4) with various 5-hydroxy-5-trifluoromethyl-4,5- dihydropyrazol-1-thiocarboxamides (5), obtained by the reaction of thiosemicarbazide with trifluoromethyl-β-diketones. All the tested compounds displayed significant to moderate in vivo anti-inflammatory activity when compared to the standard drug indomethacin, and good broad spectrum in vitro antibacterial activity against three Gram-positive and four Gram-negative bacteria when compared with cefixime.

Identification of novel molecular scaffolds for the design of MMP-13 inhibitors: A first round of lead optimization

Osteoarthritis (OA) is the leading cause of joint pain and disability in middle-aged and elderly patients, and is characterized by progressive loss of articular cartilage. Among the various matrix metalloproteinases (MMPs), MMP-13 is specifically expresse

Synthesis and antibacterial activity of some 4-(coumarin-3-yl)/Aryl 2 (3,5-dimethylpyrazol-1-yl)thiazoles

Reaction of 3-(2-bromoacetyl) coumarins (4) with 3,5-dimethylpyrazol-1- thiocarboxamide (5) results in the formation of title compounds 6. 4-Aryl-2-(3,5-dimethylpyrazol-1-yl) thiazoles (8) which could not be synthesized earlier through this method, were obtained by performing the reaction in presence of a base. All the synthesized compounds have shown moderate to significant antibacterial activity against Gram-positive bacteria namely S. aureus and B. subtilis.

Photohalogenation of 3-acetylcoumarins: Facile synthesis of 3-(2-amino-4-thiazolyl)coumarins and their conversion into 3-[2,5-dimethylpyrrol-1-yl thiazol-4-y]-coumarins

3-Acetylcoumarins react with thiourea in the presence of N-bromosuccinimide using benzoyl peroxide as radical initiator to furnish 3-(2-amino-4-thiazolyl)coumarins 1. Compounds 1 can also be obtained by reacting 3-acetylcoumarin with bromine in the presence of trichloro-(N,N-ethylene-bis-aminobenzamide)-lanthanum (III) or samarium (III) as catalyst followed by treatment with thiourea. These compounds (1) have been converted into pyrrole derivatives 2 by reacting with acetonylacetone.

Studies on Coumarin Derivatives: Part I-Synthesis of Some Substituted Thiazolyl- and Benzoxazinyl-coumarins

A number of thiazolyl- and benzoxazinyl-coumarins have been prepared and tested for their antibacterial and antifungal activities.None of the compounds is found to be active.