445291-56-5

Basic information

• Product Name: 4H-1-Benzopyran-3-carboxaldehyde, 2-(methylphenylamino)-4-oxo-
• CAS NO: 445291-56-5
• Molecular Formula: C17H13NO3
• Molecular Weight: 279.295
• Mol File: 445291-56-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4H-1-Benzopyran-3-carboxaldehyde, 2-(methylphenylamino)-4-oxo-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-3-carboxaldehyde, 2-(methylphenylamino)-4-oxo-(445291-56-5)
• EPA Substance Registry System: 4H-1-Benzopyran-3-carboxaldehyde, 2-(methylphenylamino)-4-oxo-(445291-56-5)

Safety Data

• Hazardous Substances Data: 445291-56-5(Hazardous Substances Data)

Upstream product

• 118-93-4 o-hydroxyacetophenone 
• 122-79-2 Phenyl acetate 
• 108-95-2 phenol 
• 213273-03-1 4-oxo-2-(N-phenyl)amino-4H-chromene-3-carbaldehyde 
• 74-88-4 methyl iodide 
• 113326-75-3 C-(4-oxo-4H<1>benzopyran-3-yl)-N-phenylnitrone 
• 17422-74-1 3-Formylchromone 

Downstream Products

• 1345096-79-8 3-(2-hydroxybenzoyl)-1-methylquinolin-2(1H)-one 
• 90701-02-3 Bis-<1>benzopyrano<2,3-b:3',2'-e>pyridin-5(5H),7(7H)-dion 
• 547741-59-3 ethyl (2E)-3-{2-{benzyl[(2E)-3-phenylprop-2-enyl]amino}-4-oxo-4H-1-benzopyran-3-yl}prop-2-enoate 
• 547741-58-2 ethyl (2E)-3-{2-{benzyl[(2E)-but-2-enyl]amino}-4-oxo-4H-1-benzopyran-3-yl}prop-2-enoate 
• 547741-57-1 ethyl (2E)-3-{2-[benzyl(prop-2-enyl)amino]-4-oxo-4H-1-benzopyran-3-yl}prop-2-enoate 
• 547741-56-0 2-{benzyl[(2E)-phenylprop-2-enyl]amino}-4-oxo-4H-1-benzopyran-3-carboxaldehyde 
• 547741-55-9 2-{benzyl[(2E)-but-2-enyl]amino}-4-oxo-4H-1-benzopyran-3-carboxaldehyde 
• 547741-54-8 2-[benzyl(prop-2-enyl)amino]-4-oxo-4H-1-benzopyran-3-carboxaldehyde 
• 547741-69-5 2-[benzyl(methyl)amino]-4-oxo-4H-1-benzopyran-3-carboxaldehyde 
• 71121-80-7 6H-[1]-benzopyrano[2,3-b][1,5]-benzodiazepin-13-one 
• 445291-65-6 2-(benzylamino)-4-oxochromene-3-carboxaldehyde 
• 445291-67-8 2-(p-anisylamino)-3-formylchromone 
• 445291-68-9 2-(p-tolylamino)-3-formylchromone 

Relevant articles and documents

3-Formylchromone based topoisomerase IIα inhibitors: Discovery of potent leads

Substituted 3-formylchromones were synthesized and evaluated as inhibitors of the human DNA topoisomerase IIα (hTopo-IIα) enzyme. The results of the decatenation, relaxation and DNA intercalation assays revealed that the compounds (11b, 12a, 12b, 12d, 12e, 13a and 13b) exhibited potent inhibitory activity against the hTopo-IIα enzyme, and are nonintercalating agents. These compounds also possess significant in vitro cytotoxicity (LC50 ranges from 0.5-8.6 μM) against prostate (PC-3) cancerous cell line as seen in comparison to the standard drug etoposide. To further probe the plausible mode of action of 3-formylchromone derivatives, molecular docking studies have also been carried out, which showed that the compounds under investigation fitted well in the ATP binding pocket of hTopo-IIα enzyme with good docking scores and form nonbonding interactions with the crucial residues of the catalytic site. The Royal Society of Chemistry.

A versatile route to 2-alkyl-/aryl-amino-3-formyl- and hetero-annelated-chromones, through a facile nucleophilic substitution at C2 in 2-(N-methylanilino)-3-formylchromones

The N-methylanilino group in 2-(N-methylanilino)-3-formylchromones, obtained in high yield by rearrangement of C(4-oxo-4H[1]-benzopyran-3-yl)-N-phenylnitrones to 2-anilino-3-formyl-chromones followed by N-methylation, undergoes facile nucleophilic substitution by a variety of nitrogen nucleophiles, thereby paving the way for synthesis of a variety of novel 2-substituted-3-formylchromone derivatives as well as hetero-annelated chromones.