6468-96-8

Usage

Uses

Used in Cellulose Research:
3-Phenylumbelliferone is used as a fluorescent marker for cellulose research, allowing for easier monitoring of the processes involved in cellular activities. Its fluorescent properties make it a valuable tool in studying the structure and function of cellulose in various applications.
Used in Chemical Analysis:
3-Phenylumbelliferone is used as a reference compound in chemical analysis, particularly in the identification and quantification of cellulose and other related compounds. Its distinct properties, such as its pale yellow crystalline appearance and sweet-smelling hawthorn-like scent, make it a reliable standard for comparison in various analytical techniques.
Used in Toxicity Studies:
3-Phenylumbelliferone is used as a subject in toxicity studies to understand the potential hazards associated with high concentrations of the compound. These studies are crucial in determining the safe levels of exposure and the potential applications of 3-Phenylumbelliferone in various industries, ensuring that its use does not pose significant risks to human health or the environment.
Used in Pharmaceutical Research:
3-Phenylumbelliferone is used as a starting material or intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical properties, such as its pale yellow crystalline appearance and sweet-smelling hawthorn-like scent, make it a promising candidate for the development of new drugs and therapeutic agents.
Used in Material Science:
3-Phenylumbelliferone is used in the development of new materials with unique properties, such as fluorescent materials for sensing applications or as components in advanced composites. Its chemical properties, including its pale yellow crystalline appearance and sweet-smelling hawthorn-like scent, contribute to the development of innovative materials with potential applications in various industries.

InChI:InChI=1/C15H10O3/c16-12-7-6-11-8-13(10-4-2-1-3-5-10)15(17)18-14(11)9-12/h1-9,16H

Upstream product

• 93-35-6 7-hydroxy-2H-chromen-2-one 
• 100-34-5 benzene diazonium chloride 
• 6296-55-5 acetic acid 2-oxo-3-phenyl-2H-chromen-7-yl ester 
• 17838-69-6 ethyl 3-oxo-2-phenylpropanoate 
• 108-46-3 recorcinol 
• 5841-70-3 phenyl(formyl)acetonitrile 
• 103-80-0 phenylacetyl chloride 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 103-82-2 phenylacetic acid 
• 673-22-3 2-Hydroxy-4-methoxybenzaldehyde 
• 98-09-9 benzenesulfonyl chloride 
• 52924-53-5 acetic acid 4-formyl-3-hydroxyphenyl ester 
• 59-88-1 phenylhydrazine hydrochloride 
• 98-80-6 phenylboronic acid 

Downstream Products

• 116557-43-8 6-bromo-7-hydroxy-3-phenyl-coumarin 
• 672938-07-7 8-bromo-7-hydroxy-3-phenyl-coumarin 
• 672938-12-4 6,8-dibromo-7-hydroxy-3-phenyl-coumarin 
• 2555-22-8 3-phenyl-7-methoxycoumarin 
• 1187457-62-0 7-(3,3-dimethyl-2-oxobutoxy)-3-phenylchromen-2-one 
• 887864-94-0 7-[2-(3-methoxyphenyl)-2-oxoethoxy]-3-phenylchromen-2-one 
• 195137-94-1 7-(2-oxopropoxy)-3-phenylchromen-2-one 
• 827009-19-8 7-[2-(4-methylphenyl)-2-oxoethoxy]-3-phenylchromen-2-one 
• 1210915-42-6 3-phenyl-7-O-(β-D-tetraacetylglucopyranosyl)-2H-chromen-2-one 
• 1217544-40-5 (1R,5S)-3-[(7-hydroxy-3-phenyl-2-oxo-2H-chromen-8-yl)methyl]-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one 

Relevant academic research and scientific papers

Dual Role of Oxoaldehydes: Divergent Synthesis of 3-Aryl- and 3-Aroylcoumarins

A facile and efficient synthetic approach to various valuable 3-aryl- and 3-aroylcoumarins by the direct arylation and aroylation of coumarins with glyoxals in a metal-free manner is presented. The aryl glyoxal is for the first time recognized to serve as an aryl surrogate in addition to its role as an aroyl transfer reagent via a simple switch in reaction conditions. The approach accommodates a broad substrate scope and high yields of the two types of cross-coupling reactions starting from identical starting materials.

Chlorophyll-catalyzed photochemical regioselective coumarin C-H arylation with diazonium salts

This communication describes the development of a mild method for the cross-coupling of the C3-position of coumarin with an array of diazonium salts mediated by chlorophyll as a biocatalyst via visible light catalysis. A natural pigment such as chlorophyll is used as a green photosensitizer and environmentally benign catalyst. This general and easy procedure provides a transition-metal-free alternative for the formation of 3-aryl coumarin derivatives at room temperature with good to excellent yields. This journal is

7-Hydroxycoumarins Are Affinity-Based Fluorescent Probes for Competitive Binding Studies of Macrophage Migration Inhibitory Factor

Macrophage migration inhibitory factor (MIF) is a cytokine with key roles in inflammation and cancer, which qualifies it as a potential drug target. Apart from its cytokine activity, MIF also harbors enzyme activity for keto-enol tautomerization. MIF enzymatic activity has been used for identification of MIF binding molecules that also interfere with its biological activity. However, MIF tautomerase activity assays are troubled by irregularities, thus creating a need for alternative methods. In this study, we identified a 7-hydroxycoumarin fluorophore with high affinity for the MIF tautomerase active site (Ki = 18 ± 1 nM) that binds with concomitant quenching of its fluorescence. This property enabled development of a novel competition-based assay format to quantify MIF binding. We also demonstrated that the 7-hydroxycoumarin fluorophore interfered with the MIF-CD74 interaction and inhibited proliferation of A549 cells. Thus, we provide a high-affinity MIF binder as a novel tool to advance MIF-oriented research.

1,2,3,4-Tetrahydroisoquinoline/2H-chromen-2-one conjugates as nanomolar P-glycoprotein inhibitors: Molecular determinants for affinity and selectivity over multidrug resistance associated protein 1

A series of coniugates bearing a 1,2,3,4-tetrahydroisoquinoline motif linked to substituted 7-hydroxy-2H-chromen-2-ones was synthesized and assayed through calcein-AM test in Madin-Darby Canine Kidney (MDCK) cells overexpressing P-glycoprotein (P-gp) and closely related multidrug resistance associated protein 1 (MRP1) to probe the interference with efflux mechanisms mediated by P-gp and MRP1, respectively. A number of substituents at C3 and C4 of coumarin nucleus along with differently sized and shaped spacers was enrolled to investigate the effects of focused structural modifications over affinity and selectivity. Linker length and flexibility played a key role in enhancing P-gp affinity as proved by the most potent P-gp modulator (3h, IC50 = 70 nM). A phenyl ring within the spacer (3k, 3l, 3o) and bulkier groups (Br in 3r, Ph in 3u) at coumarin C3 led to derivatives showing nanomolar activity (160 nM 50 350). Molecular docking calculations carried out on a human MDR1 homology model structure contributed to gain insights into the ligands’ binding modes. Some compounds (3d, 3h, 3l, 3r, 3t, 3u) reversed MDR thereby restoring doxorubicin cytotoxicity when co-administered with the drug into MDCK-MDR1 cells.

Antibacterial Activity and Molecular Docking Studies of a Selected Series of Hydroxy-3-arylcoumarins

Antibiotic resistance is one of the main public health concerns of this century. This resistance is also associated with oxidative stress, which could contribute to the selection of resistant bacterial strains. Bearing this in mind, and considering that f

Synthesis and biological evaluation of 3-arylcoumarin derivatives as potential anti-diabetic agents

A variety of substituted 3-arylcoumarin derivatives were synthesised through microwave radiation heating. The method has characteristics of environmental friendliness, economy, simple separation, and purification process, less by-products and high reaction yield. Those 3-arylcoumarin derivatives were screened for antioxidant, α-glucosidase inhibitory and advanced glycation end-products (AGEs) formation inhibitory. Most compounds exhibited significant antioxidant and AGEs formation inhibitory activities. Anti-diabetic activity studies showed that compounds 11 and 17 were equipotent to the standard drug glibenclamide in vivo. According to the experimental results, the target compound 35 can be used as a lead compound for the development of new anti-diabetic drugs. The whole experiment showed that anti-diabetic activity is prevalent in 3-arylcoumarins, which added a new natural skeleton to the development of anti-diabetic active drugs.

3-Aryl Coumarin Derivatives Bearing Aminoalkoxy Moiety as Multi-Target-Directed Ligands against Alzheimer's Disease

Two series of novel coumarin derivatives, substituted at 3 and 7 positions with aminoalkoxy groups, are synthesized, characterized, and screened. The effect of amine substituents and the length of cross-linker are investigated in acetyl- and butyrylcholin

Synthesis and biological evaluation of 3-arylcoumarins as potential anti-Alzheimer's disease agents

Alzheimer's disease, a neurodegenerative illness, has the extremely complex pathogenesis. Accumulating evidence indicates there is a close relationship between several enzymes and Alzheimer's disease. Various substituted 3-arylcoumarin derivatives were synthesised, and their in vitro activity, including cholinesterase inhibitory activity, monoamine oxidase inhibitory activity, and antioxidant activity were investigated. Most of the compounds exhibited high activity; therefore 3-arylcoumarin compounds have the potential as drug candidates for the treatment of Alzheimer's disease.

COMPOUNDS CONTAINING SI ATOMS FOR OPTICALLY ACTIVE DEVICES

The present invention relates to novel 2-oxo-2H-chromen compounds, particularly to compounds comprising a photoactive unit, said novel compounds being particularly suitable for compositions and ophthalmic devices as well as to compositions and ophthalmic

Design, synthesis and evaluation of novel multi-target-directed ligands for treatment of Alzheimer's disease based on coumarin and lipoic acid scaffolds

A novel series of coumarin-lipoic acid conjugates were synthesized via cycloaddition click reaction to find out new multi-target-directed ligands (MTDLs) for treatment of Alzheimer's disease (AD). All of synthesized compounds were screened for neuroprotec