55736-88-4

Basic information

• Product Name: Benzonitrile, 4-(4-oxo-4H-1-benzopyran-2-yl)- (9CI)
• Synonyms: Benzonitrile, 4-(4-oxo-4H-1-benzopyran-2-yl)- (9CI)
• CAS NO: 55736-88-4
• Molecular Formula: C₁₆H₉NO₂
• Molecular Weight: 247.24816
• Product Categories: FLAVONE
• Mol File: 55736-88-4.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzonitrile, 4-(4-oxo-4H-1-benzopyran-2-yl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzonitrile, 4-(4-oxo-4H-1-benzopyran-2-yl)- (9CI)(55736-88-4)
• EPA Substance Registry System: Benzonitrile, 4-(4-oxo-4H-1-benzopyran-2-yl)- (9CI)(55736-88-4)

Safety Data

• Hazardous Substances Data: 55736-88-4(Hazardous Substances Data)

Upstream product

• 582-24-1 1-phenyl-2-hydroxyethanone 
• 105-07-7 4-cyanobenzaldehyde 
• 3033-94-1 4-<3-(2-Hydroxy-phenyl)-3-oxo-propen-(1)-yl>-benzonitril 
• 118-93-4 o-hydroxyacetophenone 
• 20525-20-6 4'-bromoflavone 
• 201230-82-2 carbon monoxide 
• 623-00-7 4-bromobenzenecarbonitrile 

Downstream Products

• 20093-91-8 4-(4-oxo-4H-chromen-2-yl)benzoic acid 

Relevant articles and documents

CHROMEN-4-ONE DERIVATIVES, SUCH AS E.G. FLAVONES, FOR USE AS CK2 INHIBITORS FOR THE TREATMENT OF NEUROINFLAMMATION

Chromen-4-one derivatives, such as e.g. flavone derivatives and pharmaceutical compositions thereof are disclosed. In some instances, the compounds have increased aqueous solubility, bioavailability, and ability to cross the blood-brain-barrier. The compounds may be used to inhibit casein kinase 2 (CK2) activity and/or to treat diseases and conditions mediated at least in part by CK2 enzyme, such as e.g. inflammation, in particular neuroinflammation, or other diseases, such as e.g. cancer, cardiac hypertrophy, cystic fibrosis, a neurodegenerative disease, bipolar disorder, depression, a viral infection, obesity, diabetes mellitus, atherosclerosis, epilepsy, or any combination thereof.

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.