1994-13-4

Usage

Uses

Used in Fluorescence Assays and Biological Imaging:
6-FLUORO-4-HYDROXYCOUMARIN is used as a fluorescent probe for its ability to produce green fluorescence under ultraviolet light, making it suitable for various fluorescence assays and biological imaging applications.
Used in Pharmaceutical and Agrochemical Synthesis:
6-FLUORO-4-HYDROXYCOUMARIN is used as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and agricultural products.
Used in Anticancer Applications:
6-FLUORO-4-HYDROXYCOUMARIN is studied for its potential as an anticancer agent, with research exploring its effects on various types of cancer and its potential to enhance the efficacy of existing treatments.
Used in Anti-inflammatory Applications:
6-FLUORO-4-HYDROXYCOUMARIN is also being investigated for its anti-inflammatory properties, with potential applications in the development of treatments for inflammatory conditions.

InChI:InChI=1/C9H5FO3/c10-5-1-2-8-6(3-5)7(11)4-9(12)13-8/h1-4,12H

Upstream product

• 1994-31-6 2-(4-fluorophenoxy)carbonyl acetic acid 
• 371-41-5 4-Fluorophenol 
• 141-82-2 malonic acid 
• 394-32-1 1-(5-fluoro-2-hydroxyphenyl)ethan-1-one 
• 105-58-8 Diethyl carbonate 
• 1810-25-9 bis(4-fluorophenyl) malonate 

Downstream Products

• 1152668-99-9 C₁₅H₈ClFO₂ 
• 1159020-27-5 C₁₅H₈F₂O₂S 
• 1159020-24-2 C₁₅H₉FO₂S 
• 1159020-21-9 C₁₆H₁₁FO₂S 
• 1187472-29-2 6-fluoro-4-(phenylethynyl)-2H-chromen-2-one 
• 1187472-30-5 6-fluoro-4-((4-methoxyphenyl)ethynyl)-2H-chromen-2-one 
• 1233097-49-8 C₂₅H₁₁F₅O₆ 
• 1258432-44-8 (2R,3R)-8-fluoro-3-(4-methoxyphenyl)-2-nitro-2H-furo[3,2-c]chromen-4(3H)-one 
• 1338247-94-1 6-fluoro3-(2-hydroxybenzylidene)chroman-2,4-dione 
• 1338247-95-2 6-fluoro-3-(2-hydroxy-3-methoxybenzylidene)chroman-2,4-dione 
• 1537195-73-5 4-((6-amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)(6-fluoro-4-hydroxy-2-oxo-2H-chromen-3-yl)methyl)benzonitrile 
• 1537195-77-9 6-amino-5-((1,3-diphenyl-1H-pyrazol-4-yl)(6-fluoro-4-hydroxy-2-oxo-2H-chromen-3-yl)methyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 
• 1537195-78-0 6-amino-5-((6-fluoro-4-hydroxy-2-oxo-2H-chromen-3-yl)(3-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-4-yl)methyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 

Relevant academic research and scientific papers

Copper(II)-Catalyzed Tandem Reaction: Synthesis of Furo[3,2- c]coumarin Derivatives and Evaluation for Photophysical Properties

An efficient protocol for synthesizing furo[3,2-c]coumarin derivatives is described. The novel reaction could afford the desired furocoumarins with good to excellent yields in a mild and rapid manner. Large substrate scope screening and scale-up preparation have also been accomplished, and selected compounds were evaluated for their photophysical properties.

Synthesis and biological evaluation of bis-N2,N2′-(4-hydroxycoumarin-3-yl)ethylidene]-2,3-dihydroxysuccinodihydrazides

A series of N2,N2′-bis[4-hydroxycoumarin-3-yl)ethylidene]-2,3-dihydroxysuccino-hydrazides, containing 4-hydroxycoumarin, hydrazine and tartaric acid moieties, have been prepared and examined for possible biological activity. Several of these compounds exhibit promising HIV-1 integrase inhibition (IC50 = 3.5 μM), and anti-T. brucei (32% viability) and anti-mycobacterial (Visual MIC90 = 15.63 μM) activity.

Synthesis of substituted 4-(4-((3-Nitro-2-oxo-2H-chromene-4-yl)amino)phenyl)morpholine-3-one coumarin derivatives

A series of novel 4-(4-amino phenyl) morpholine-3-one substituted coumarin derivatives have been prepared by chloramine coupling reaction and were identified. The novel synthetic route involves nucleophilic substitution reaction of 4-chloro-3-nitro-2H-chromene-2- one with 4-(4-amino phenyl)morpholine-3-one. Due to the presence of nitro group in coumarin derivatives make substitution reaction easy and convenient at low temperature. Using DMF as solvent and K2CO3 as base various substituted 4-(4-((3-nitro-2-oxo-2H-chromen- 4-yl)amino)phenyl)morpholine-3-one derivatives (YS-1 to YS-10) can be obtain in good yield and high purity. Structural characterization of all synthesized compound was done by NMR, Mass and IR spectra.

Regioselective Synthesis of 4,5-Dihydro-6H-oxepino[3,2-c]chromene-2,6(3H)-diones through Palladium-Catalyzed Intramolecular Alkoxycarbonylation of 3-Allyl-4-hydroxycoumarins

Seven-membered ring lactones fused to coumarin scaffolds were obtained via a palladium-catalyzed regioselective intramolecular alkoxycarbonylation under a CO atmosphere. Cyclocarbonylation of 3-allyl-4-hydroxycoumarin derivatives was accessed in the absen

Annulation of β-naphthols and 4-hydroxycoumarins with vinylsulfonium salts: Synthesis of dihydrofuran derivatives

A new synthetic approach to dihydrofuran derivatives via the annulation reaction of β-naphthols and 4-hydroxycoumarins with vinylsulfonium salts has been developed. A variety of dihydrofuran derivatives were prepared in moderate to good yields under mild conditions. The products could be readily transformed to the corresponding furans via the dehydrogenation with DDQ.

Synthesis of furo[3,2-c]coumarins via I2/TBHP-mediated reaction of 4-hydroxycoumarins with terminal alkynes

An efficient I2/TBHP-mediated process for the formation of furo[3,2-c]coumarins from readily available materials has been developed. This process for the formation of furo[3,2-c]coumarins is quite environmental friendly and atom-economical.

Synthesis and biological evaluation of 4 arylcoumarin analogues as tubulin-targeting antitumor agents

The synthesis of twenty-six 4-arylcoumarin analogues of combretastatin A-4 (CA-4) led to the identification of two new compounds (25 and 26) with strong cytotoxic activity. Both compounds had a high cytotoxic effect on a CA-4-resistant colon adenocarcinoma cell line (HT29D4). The compounds affected cell cycle progression characterized by a mitotic block. The activity of these compounds against microtubules both in vitro and in cells was examined and both compounds were found to potently inhibit in vitro microtubule formation via a sub-stoichiometric mode like CA-4. By immunofluorescence, it was observed that both compounds induced strong microtubule network disruption. Our results provide a strong experimental basis to develop new potent anti-tubulin molecules targeting CA-4-resistant cancer cells.

Palladium-catalyzed [2+2+1] oxidative annulation of 4-hydroxycoumarins with unactivated internal alkynes: Access to spiro cyclopentadiene-chroman-2,4-dione complexes

Herein, we report our new results regarding a palladium-catalyzed [2+2+1] oxidative annulation of 4-hydroxycoumarins with unactivated internal alkynes, which affords a new class of compounds: the spiro cyclopentadiene-chroman-2,4- diones.

Palladium-catalyzed oxidative annulation via C-H/N-H functionalization: Access to substituted pyrroles

Pyrroles, ubiquitous bioactive heterocycles in nature, are readily prepared via a palladium-catalyzed oxidative annulation of cyclic trans-enamines to various internal alkynes in the absence of a directing group. Copyright

Coumarin-Based Bioactive Compounds: Facile Synthesis and Biological Evaluation of Coumarin-Fused 1,4-Thiazepines

As part of our ongoing studies on the synthesis of bioactive coumarin compounds, we synthesized a series of new coumarin-fused 1,4-thiazepines using a simple method. The biological activity of target compounds along with 3-(2-hydroxybenzylidene)chroman-2,4-dione intermediates was screened by evaluation of their antioxidant and cytotoxic activities. The antioxidant activity was assessed using two methods, namely, 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging method and ferric reducing antioxidant power (FRAP) assay. 4-Methoxyphenolic compound 5d in thiazepine series showed the most potent scavenging activity, while the 4-bromophenolic derivative 5b was the most efficient compound in FRAP assay. Also, the result of cytotoxic evaluation using MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide] assay demonstrated that compound 5b is at least twofold more potent than etoposide against MCF-7, SK-N-MC, and MDA-MB 231 cell lines. A series of new coumarin-fused 1,4-thiazepines were synthesized using a simple method. The biological activities of target compounds were screened by evaluation of their antioxidant and cytotoxic activities.