2650-14-8

Usage

Uses

Used in Pharmaceutical Industry:
3-bromo-2-hydroxy-4H-chromen-4-one is used as a pharmaceutical candidate for its potential antioxidant, anti-inflammatory, and anticancer properties. Its unique chemical structure allows it to modulate various biological pathways, making it a promising agent for the development of new drugs to treat various diseases.
Used in Drug Development:
3-bromo-2-hydroxy-4H-chromen-4-one is used as a lead compound in drug development due to its potential biological activities. Researchers are exploring its therapeutic potential and optimizing its chemical structure to enhance its efficacy and safety for use in treating specific medical conditions.
Used in Biological Imaging:
3-bromo-2-hydroxy-4H-chromen-4-one is used as a fluorescent probe in biological imaging. Its unique fluorescent properties allow researchers to visualize and study cellular processes and interactions at the molecular level, providing valuable insights into the mechanisms of various biological phenomena.

Upstream product

• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 86795-49-5 3-(phenyl-λ³-iodanylidene)chromane-2,4-dione 
• 108-95-2 phenol 
• 3515-42-2 3-iodo-4-hydroxycoumarin 

Downstream Products

• 69538-20-1 3-mercapto-4-hydroxycoumarin 
• 132590-25-1 2-<2-hydroxybenzoyl>-3-phenyl-4H-furo<3,2-c><1>benzopyran-4-one 
• 132590-23-9 2,3-dihydro-2-<2-hydroxybenzoyl>-3-phenyl-4H-furo<3,2-c><1>benzopyran-4-one 
• 50329-91-4 4-chloro-3-formylcoumarin 
• 132590-24-0 bismethine<1>benzopyran-2,4-dione ether 
• 20261-31-8 4-hydroxy-3-nitrocoumarin 
• 18714-37-9 4-hydroxy-3-(phenylsulfanyl)-2H-chromen-2-one 
• 1218756-44-5 4-(4-hydroxy-2-oxo-2H-1-benzopyran-2-one-3-yl)-3-methyl-1-phenylpyrazolo[3,4;2,3]-4H-pyrano[3,2-b]-1-benzopyran-5-one 
• 1143505-49-0 2-(4-(tert-butyl)phenyl)-4H-furo[3,2-c]chromen-4-one 

Relevant academic research and scientific papers

Synthesis of: Cis / trans -dihydrochromenones via a photoinduced rearrangement of 4-phenyl-3-aryl/cyclohexenylcoumarins

A concise and environmentally friendly protocol has been developed for the synthesis of cis-dihydrochromenones and trans-dihydrochromenones in EtOH at room temperature. Irradiation of 4-phenyl-3-arylcoumarins in EtOH with 313 nm UV light under an argon atmosphere at room temperature gave cis-4b,15c-dihydro-16H-benzofuro[3′,2′:7,8]phenanthro[9,10-c]chromen-16-ones and cis-8c,14b-dihydro-9H-benzo[11,12]chryseno[5,6-c]chromen-9-ones in good yields. And an analogous treatment of 4-phenyl-3-alkenylcoumarins as 4-phenyl-3-arylcoumarins provided trans-1,2,3,4,4a,14b-hexahydro-5H-phenanthro[9,10-c]chromen-5-ones. The described photorearrangement proceeded smoothly without the addition of any transition metals and additives. The photorearrangement of 4-phenyl-3-arylcoumarins is believed to proceed via 6π-electrocyclization, a [1,3]-hydrogen shift and keto-enol isomerization.

Highly efficient construction of bisspirooxindoles containing vicinal spirocenters through an organocatalytic modified Feist-Bénary reaction

We have developed an organocatalytic modified Feist-Bénary reaction of cyclic dicarbonyl compounds, isatins and cyclic α-bromo dicarbonyl compounds. This method affords bisspirooxindole-fused dihydrofurans containing two vicinal spiro centers. To the best

Synthesis of antimicrobial 2,9,10-trisubstituted-6-oxo-7,12-dihydro-chromeno[3,4-b]quinoxalines

A new series of 2,9,10-trisubstituted-6-oxo-7,12-dihydro-chromeno[3,4-b]quinoxalines was synthesized and submitted to antibacterial and antifungal activities. Result of the antimicrobial screening showed the compound 4j being the most effective among the various treatments in antimicrobial screening. Compounds 4c, 4d, 4k, and 4l showed moderate activity against the microorganisms tested.

Synthesis of Polycyclic Heteroaromatic Coumarins via Photoinduced Dehydrogenative Annulation of 4-Phenyl-3-heteroarylcoumarins

An efficient, oxidant and metal-free synthesis of polycyclic heteroaromatic coumarins was developed. H-Furo[2′,3′:3,4]naphtho[2,1-c]chromen-4-one (2a-2f), 1H-benzofuro[2′,3′:3,4]naphtho[2,1-c]chromen-1-one (2g-2j), and 4H-thieno[2′,3′:3,4]naphtho[2,1-c]ch

Convenient Michael addition/β-elimination approach to the synthesis of 4-benzyl- and 4-aryl-selenyl coumarins using diselenides as selenium sources

A concise and efficient, two-step approach toward 4-organoselenyl coumarin derivatives from the easily available 4-hydroxycoumarins, is reported. The synthesis was based on conventional tosylation followed by a tandem selena-Michael addition/β-elimination reaction of an aryl-/benzyl-selenolate anion on the corresponding 4-tosyloxycoumarins. The selenolate anions were conveniently generated in situ by exposure of the corresponding diselenides to NaBH4. Selected compounds demonstrated to exhibit antioxidant properties in mice cortex and hippocampus.

Reaction of 4-hydroxycoumarin or its O-substituted derivatives with diatomic interhalogens: ICl and IBr

Herein, we present some aspects regarding the iodination/bromination of 4-hydroxycoumarin or its O-methyl or O-acetyl derivatives with iodine monochloride or iodine monobromide as halogenation reagents. Also, the investigation of photochemical transformation of the three 3-iodocoumarins was investigated for the first time.

Pd-catalyzed cross-coupling study of bi-functional 3-bromo-4-trifloxycoumarins with triarylbismuth reagents

Abstract The cross-coupling reactions of functionalized 3-bromo-4-trifloxycoumarins have been explored with threefold arylating triarylbismuth reagents. These palladium-catalyzed reactions afforded chemo-selective C-4 arylations with the facile formation of 3-bromo-4-arylcoumarins in good to high yields. Additionally, palladium-catalyzed arylations of functionalized 3-bromo-4-arylcoumarins also participated in the second arylation to give functionalized 3,4-diarylcoumarins in high yields.

An efficient regioselective bromination protocol of activated coumarins using 2,4,4,6-tetrabromo-2,5-cyclohexadienone

2,4,4,6-Tetrabromo-2,5-cyclohexadienone mediated bromination of a wide assortment of activated coumarins in acetonitrile has been accomplished with high regioselectivity and good to excellent yields. The selectivity and efficiency of bromination were found to be markedly dependent on electronic factors, particularly degree of electron withdrawal from electron-releasing 7-oxygenated substituents to the C-3 position of the α-pyrone moiety by vinylogous resonance and the presence of nucleophilic additives such as water and tetra-n-butylammonium bromide in the reaction medium. The sole by-product of the reaction was converted back to the reagent by oxidation with KBr-KBrO 3, which was recycled three times without significant loss of efficiency.

Dual-mode fluorescence switching of photochromic bisthiazolylcoumarin

Three new photochromic coumarins were synthesized. Fluorescence of the open form of 7-hydroxy-3,4-bisthiazolyl-coumarin increased to 1400% by changing the pH only slightly from 6.05 to 7.58. This was subsequently quenched to 1.5% of the maximum intensity at the UV photostationary state in water-methanol media.

Synthesis, antibacterial, and analgesic activity of novel 4-hydroxy-3-(phenylthio)-2H-chromen-2-ones and 4-Hydroxy-3-[imidazol/tetrazolo- 2-yl)thio]-2H-chromen-2-ones

A mild and efficient synthesis of new 4-hydroxy-3-(phenylthio)-2H-chromen- 2-ones 4a-k and 4-hydroxy-3-[imidazol/tetrazolo-2-yl)thio]-2H-chromen-2-ones 6a-d is described. The compounds 4a-c were further subjected to oxidation by m-CPBA to obtain 3-(phenylsulfonyl)-4-hydroxy-2H-chromen-2-ones 5a-c. The structures of the resulted new compounds were established by IR, 1H NMR, mass, and elemental analysis. All the synthesized compounds were subjected to antibacterial activity against the Gram positive bacteria Staphylococcus aureus, Bacillus subtilis, and Streptococcus haemolytius and the Gram negative bacteria Salmonella typhi, Escherichia coli, Pseudomonas aeruginosa, and Klebsiella pneumonia. The analgesic activity was carried out using Swiss albino male mice by abdominal concentration method. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. Copyright Taylor &Francis Group, LLC.