36715-65-8

Basic information

• Product Name: 1-(2-hydroxyphenyl)-3-anthracen-9-ylprop-2-en-1-one
• Synonyms: 1-(2-hydroxyphenyl)-3-anthracen-9-ylprop-2-en-1-one
• CAS NO: 36715-65-8
• Molecular Weight: 324.379
• Mol File: 36715-65-8.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 1-(2-hydroxyphenyl)-3-anthracen-9-ylprop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-hydroxyphenyl)-3-anthracen-9-ylprop-2-en-1-one(36715-65-8)
• EPA Substance Registry System: 1-(2-hydroxyphenyl)-3-anthracen-9-ylprop-2-en-1-one(36715-65-8)

Safety Data

• Hazardous Substances Data: 36715-65-8(Hazardous Substances Data)

Usage

Description

1-(2-hydroxyphenyl)-3-anthracen-9-ylprop-2-en-1-one is a chemical compound with the molecular formula C25H18O2. It is a derivative of anthracene, a tricyclic aromatic hydrocarbon, and contains a hydroxyphenyl and propenone moiety. 1-(2-hydroxyphenyl)-3-anthracen-9-ylprop-2-en-1-one is a yellow crystalline solid and has potential applications in fields such as organic synthesis and material science. Its unique structure and properties make it a valuable molecule for further research and development in various industrial and scientific applications.

Uses

Used in Organic Synthesis:
1-(2-hydroxyphenyl)-3-anthracen-9-ylprop-2-en-1-one is used as an intermediate in the synthesis of various organic compounds for [application reason] its unique structure and reactivity.
Used in Material Science:
In the field of material science, 1-(2-hydroxyphenyl)-3-anthracen-9-ylprop-2-en-1-one is used as a component in the development of new materials for [application reason] its potential to contribute to the properties of these materials, such as optical, electronic, or mechanical characteristics.
Used in Pharmaceutical Research:
1-(2-hydroxyphenyl)-3-anthracen-9-ylprop-2-en-1-one is also used as a starting material in the pharmaceutical industry for [application reason] its potential to be modified and developed into new drugs with specific therapeutic properties.
Used in Chemical Research:
1-(2-hydroxyphenyl)-3-anthracen-9-ylprop-2-en-1-one is used in chemical research as a model system for studying the properties and reactions of aromatic hydrocarbons and their derivatives for [application reason] its unique structural features and potential to provide insights into the behavior of similar compounds.
Used in Dye and Pigment Industry:
1-(2-hydroxyphenyl)-3-anthracen-9-ylprop-2-en-1-one is used as a precursor in the production of dyes and pigments for [application reason] its yellow crystalline solid form and potential to yield colored products with specific characteristics.
Used in Analytical Chemistry:
In analytical chemistry, 1-(2-hydroxyphenyl)-3-anthracen-9-ylprop-2-en-1-one is used as a reference compound or standard for [application reason] its well-defined chemical structure and properties, which can be used to calibrate instruments or validate analytical methods.

Upstream product

• 118-93-4 o-hydroxyacetophenone 
• 642-31-9 9-anthracene aldehyde 
• 120-12-7 anthracene 

Downstream Products

• 1290176-42-9 C₂₃H₁₈N₂O 

Relevant articles and documents

Convenient synthesis of flavanone derivatives via oxa-Michael addition using catalytic amount of aqueous cesium fluoride

A total of 36 flavanones, which included polycyclic aromatic and heterocyclic rings, were readily synthesized via oxa-Michael addition from the corresponding hydroxychalcones with a catalytic amount of aqueous cesium fluoride solution under mild conditions. This method could be applied to the scalable synthesis of eriodictyol as a known potent inhibitor of the SARS-CoV-2 spike protein.

Synthesis and antiviral activity of 2-aryl-4H-chromen-4-one derivatives against Chikungunya virus

A series of nineteen 2-aryl-4H-chromen-4-one derivatives 2a-2s were synthesized and evaluated for their antiviral activity against Chikungunya virus (LR2006-OPY1) in Vero cell culture by CPE reduction assay. Three compounds 2a, 2b and 2g, were found to be active at concentration of (IC50) 0.44 μM, 0.45 μM and 2.02 μM, respectively. Compounds having heterocyclic ring 2a and 2b at the 2nd position of the chromenone were found to be potent inhibitor of ChikV. Cytotoxicity studies were performed using Vero cell culture, compounds 2a and 2b exhibited SI of ≥100. Molecular docking simulation has been carried out to understand the possible mechanism of action.

Monoamine oxidase inhibitory activity of 2-aryl-4H-chromen-4-ones

A series of twenty 2-aryl-4H-chromen-4-one (flavones) derivatives (3a-3s) were synthesized and tested for hMAO inhibitory activity. Fifteen compounds (3a, 3c, 3e-3h, 3j-3p, 3r, 3s) were found to be selective towards MAO-B, while 3d was selective towards MAO-A, and 3b, 3i and 3q were non-selective. Experimental Selectivity Index for MAO-B ranges from 2.0 (3g, 3p) to 30.0 (3j). Compound 3j, which is carrying 3,4-di-OMeC6H3 groups at R position on the molecule, was found to be potent MAO-B inhibitor amongst the fifteen with Ki value for MAO-B of 0.16 ± 0.01 μM comparable to that of standard drug, Selegiline (Ki for MAO-B is 0.16 ± 0.01 μM). Compound 3j also appeared as the most selective MAO-B inhibitor according to its best selectivity index (30.0), which is comparable to that of Selegiline (SIMAO-B = 35.0). Molecular docking and molecular dynamics simulation studies were carried out using Autodock-4.0 and Amber12 to understand the molecular level interaction and energy relation of MAO isoforms with selective inhibitors (3d and 3j). Simulation results are in good agreement with the experimental results. Leads identified may further be explored to develop potent isoform specific inhibitors of MAO.