71592-11-5

Basic information

• Product Name: 3-[(Z)-ANILINOMETHYLIDENE]-2H-CHROMENE-2,4-DIONE
• Synonyms: 3-[(Z)-ANILINOMETHYLIDENE]-2H-CHROMENE-2,4-DIONE;AURORA KA-4147;(3Z)-3-[(phenylamino)methylidene]-3,4-dihydro-2H-1-benzopyran-2,4-dione
• CAS NO: 71592-11-5
• Molecular Formula: C₁₆H₁₁NO₃
• Molecular Weight: 265.26
• Mol File: 71592-11-5.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-[(Z)-ANILINOMETHYLIDENE]-2H-CHROMENE-2,4-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[(Z)-ANILINOMETHYLIDENE]-2H-CHROMENE-2,4-DIONE(71592-11-5)
• EPA Substance Registry System: 3-[(Z)-ANILINOMETHYLIDENE]-2H-CHROMENE-2,4-DIONE(71592-11-5)

Safety Data

• Hazardous Substances Data: 71592-11-5(Hazardous Substances Data)

Upstream product

• 39079-62-4 chromone-3-carboxylic acid 
• 62-53-3 aniline 
• 51751-34-9 4-hydroxycoumarin-3-carboxaldehyde 
• 80-62-6 methacrylic acid methyl ester 
• 113326-75-3 N-((4-oxo-4H-chromen-3-yl)methylene)aniline oxide 
• 109-92-2 ethyl vinyl ether 
• 79-06-1 2-propenamide 
• 78-94-4 methyl vinyl ketone 
• 1191-99-7 2,3-dihydro-2H-furan 

Relevant articles and documents

Synthesis and evaluation of chromone derivatives as inhibitors of monoamine oxidase

Abstract: Based on reports that chromone compounds are good potency inhibitors of monoamine oxidase (MAO), the present study evaluates the effect of substitution with flexible side chains on the 3 position on MAO inhibition potency. Fifteen chromone derivatives were synthesised by reacting aromatic and aliphatic amines and alcohols with chromone 3-carboxylic acid in the presence of carbonyldiimidazole (CDI). This yielded chromane-2,4-dione and ester chromone derivatives. Generally, the esters exhibited weak MAO inhibition, while the chromane-2,4-dione derivatives showed promise as selective MAO-B inhibitors with IC50 values in the micromolar range. Compound 14b, 3-[(benzylamino)methylidene]-3,4-dihydro-2H-1-benzopyran-2,4-dione, was the most potent MAO-B inhibitor with an IC50 value of 638?μM. This compound was shown to be a reversible and competitive MAO-B inhibitor with a Ki of 94?μM. In conclusion, the effect of chain elongation and introduction of flexible substituents on position 3 of chromone were explored and the results showed that aminomethylidene substitution is preferable over ester substitution. Good potency MAO-B inhibitors may act as leads for the design and development of therapy for Parkinson’s disease where these agents reduce the central metabolism of dopamine. Graphical abstract: [Figure not available: see fulltext.].

Investigations on peri-, regio- and stereoselectivities in thermal cycloadditions involving C-(4-oxo-4H[1]benzopyran-3-yl)-N-phenylnitrones: Role of steric factors and secondary interactions in 1,3-dipolar cycloadditions

Complete peri-, regio- and stereoselectivities in thermal reactions of C-(4-oxo-4H[1]benzopyran-3-yl)-N-phenylnitrones with both electron-rich and electron-deficient olefins have been investigated. This conjugated nitrone undergoes frontier-orbital (LUMO-