4613-53-0

Basic information

• Product Name: 6-AMINOFLAVONE 97
• Synonyms: 6-AMINOFLAVONE 97;6-Aminoflavone 97%;6-amino-2-phenylchromen-4-one
• CAS NO: 4613-53-0
• Molecular Formula: C₁₅H₁₁NO₂
• Molecular Weight: 237.257
• Product Categories: Benzopyrans;Building Blocks;Heterocyclic Building Blocks
• Mol File: 4613-53-0.mol
• Article Data: 10

Chemical Properties

• Melting Point: 196-200 °C(lit.)
• Boiling Point: 451.6°C at 760 mmHg
• Flash Point: 239.8°C
• Appearance: /
• Density: 1.306g/cm³
• Vapor Pressure: 2.4E-08mmHg at 25°C
• Refractive Index: 1.677
• PKA: 3.26±0.40(Predicted)
• CAS DataBase Reference: 6-AMINOFLAVONE 97(CAS DataBase Reference)
• NIST Chemistry Reference: 6-AMINOFLAVONE 97(4613-53-0)
• EPA Substance Registry System: 6-AMINOFLAVONE 97(4613-53-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 4613-53-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H11NO2/c16-11-6-7-14-12(8-11)13(17)9-15(18-14)10-4-2-1-3-5-10/h1-9H,16H2

Upstream product

• 4010-28-0 5'-bromo-2'-benzoyloxy-acetophenone 
• 1450-75-5 5-Bromo-2-hydroxyacetophenone 
• 1218-80-0 6-bromoflavone 
• 103-90-2 4-acetaminophenol 
• 100-52-7 benzaldehyde 
• 24449-58-9 5′-acetamino-2′-hydroxychalcone 
• 7298-67-1 5-acetamido-2-hydroxyacetophenone 
• 36773-22-5 1-phenyl-3-(2'-hydroxy-5'-acetamidophenyl)-1,3-propanedione 
• 18467-10-2 N-(4-oxo-2-phenyl-4H-chromen-6-yl)acetamide 
• 98-88-4 benzoyl chloride 
• 50-80-6 5-amino-2-hydroxyacetophenone 
• 2623-33-8 4-acetoxyacetanilide 
• 123-30-8 4-amino-phenol 
• 51-66-1 4-methoxyacetanilide 

Downstream Products

• 159679-98-8 1-(4-Methoxy-benzoyl)-3-(4-oxo-2-phenyl-4H-chromen-6-yl)-thiourea 
• 159679-97-7 1-(4-Methyl-benzoyl)-3-(4-oxo-2-phenyl-4H-chromen-6-yl)-thiourea 
• 159679-95-5 N-benzoyl-N'-(2-phenyl-4-oxo-4H-<1>benzopyran-6-yl)thiourea 
• 159679-96-6 1-(4-Chloro-benzoyl)-3-(4-oxo-2-phenyl-4H-chromen-6-yl)-thiourea 
• 1422722-54-0 4-benzylidene-1-(4-oxo-2-phenyl-4H-chromen-6-yl)-2-phenyl-1H-imidazol-5-one 
• 1422722-55-1 4-(4-methoxybenzylidene)-1-(4-oxo-2-phenyl-4H-chromen-6-yl)-2-phenyl-1H-imidazol-5-one 
• 1422722-56-2 4-(3,4-dichlorobenzylidene)-1-(4-oxo-2-phenyl-4H-chromen-6-yl)-2-phenyl-1H-imidazol-5-one 
• 1422722-57-3 4-(3,4-dimethoxybenzylidene)-1-(4-oxo-2-phenyl-4H-chromen-6-yl)-2-phenyl-1H-imidazol-5-one 
• 1422722-58-4 4-(4-hydroxybenzylidene)-1-(4-oxo-2-phenyl-4Hchromen-6-yl)-2-phenyl-1H-imidazol-5-one 

Relevant articles and documents

N-Benzylation of 6-aminoflavone by reductive amination and efficient access to some novel anticancer agents via topoisomerase II inhibition

Series of novel N-benzyl derivatives of 6-aminoflavone (9a–n) were synthesized and evaluated for anticancer and topoisomerase II enzyme inhibition activity. All the synthesized compounds were screened for in vitro anticancer activity against human breast cancer cell line (MCF-7) and human lung cancer cell line (A-549). Among the synthesized compounds, 9f and 9g were found to be the most potent anticancer agents against human breast cancer cell line (MCF-7) with IC50 values of 9.35?μM and 9.58?μM, respectively. Compounds 9b, 9c and 9n exhibited promising anticancer activity against human lung cancer cell line (A-549) with 43.71%, 46.48% and 44.26% inhibition at the highest concentration of 10?μM, respectively. Compounds 9c, 9f and 9g have ability to inhibit the topoisomerase II enzyme. Compound 9f showed most potent topoisomerase II enzyme inhibition activity with IC50 value of 12.11?μM. Further, these compounds have a high potential to be developed as a promising topoisomerase II inhibitors.

Synthesis and antiproliferative activity of new 1,2,3-triazole/flavone hybrid heterocycles against human cancer cell lines

A series of new 1,2,3-triazole/flavone hybrid heterocycles were synthesized from 6-amino flavone via key intermediate N-propargyl flavone 6 by adopting the Sharpless Click reaction. Copper(I) catalyzed 1,3-dipolar cycloaddition reaction that gave products in high yields. All the synthesized compounds were screened for their in vitro antiproliferative activity against four human cancer cell lines, HeLa (cervical cancer cell line), MIA PaCa (pancreatic cancer cell line), MDA-MB-231 (breast cancer cell line), and IMR 32 (neuroblastoma cancer cell line). Compounds 7a, 7b, 7d, 7g (GI50 = 0.01–0.68 μM) demonstrated promising antiproliferative activity.

COMPOUNDS FOR THE TREATMENT OF AMYLOID-ASSOCIATED DISEASES

This invention provides novel compounds of formulae (I) or (II) or a stereoisomer, enantiomer, racemic, or tautomer thereof, (I) (II) wherein the substituents are as defined in the specification. The present invention also relates to the novel compounds for use as a medicine, more in particular for the prevention or treatment of amyloid-related diseases, more specifically certain neurological disorders, such as disorders collectively known as tauopathies, disorders characterized by cytotoxic α-synuclein amyloidogenesis. The present invention also relates to the use of said novel compounds for the manufacture of medicaments useful for treating such amyloid-related diseases. The present invention further relates to pharmaceutical compositions including said novel compounds and to methods for the preparation of said novel compounds.