5725-79-1

Basic information

• Product Name: 3-AMINO-4-HYDROXY-CHROMEN-2-ONE
• Synonyms: 3-AMINO-4-HYDROXY-CHROMEN-2-ONE;AKOS AU-SVL-1
• CAS NO: 5725-79-1
• Molecular Formula: C₉H₇NO₃
• Molecular Weight: 177.16
• Mol File: 5725-79-1.mol
• Article Data: 21

Chemical Properties

• Melting Point: 225 °C (decomp)
• Boiling Point: 372.1±42.0 °C(Predicted)
• Appearance: /
• Density: 1.505±0.06 g/cm3(Predicted)
• PKA: 4.77±0.20(Predicted)
• CAS DataBase Reference: 3-AMINO-4-HYDROXY-CHROMEN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AMINO-4-HYDROXY-CHROMEN-2-ONE(5725-79-1)
• EPA Substance Registry System: 3-AMINO-4-HYDROXY-CHROMEN-2-ONE(5725-79-1)

Safety Data

• Hazardous Substances Data: 5725-79-1(Hazardous Substances Data)

Upstream product

• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 13948-45-3 3-acetamido-4-hydroxycoumarin 
• 81327-41-5 5-(2-Methoxymethoxy-phenyl)-oxazole-4-carboxylic acid methyl ester 
• 52140-71-3 4-hydroxy-3-phenylazo-cumarine 
• 5876-91-5 2-(methoxymethyloxy)benzoic acid 
• 20261-31-8 4-hydroxy-3-nitrocoumarin 

Downstream Products

• 5186-54-9 3-diazobenzopyran-2,4(3H)-dione 
• 90515-57-4 5-Methyl-3-phenyl-isoxazole-4-carboxylic acid (4-hydroxy-2-oxo-2H-chromen-3-yl)-amide 
• 90515-64-3 2-(2-Chloro-phenoxy)-N-(4-hydroxy-2-oxo-2H-chromen-3-yl)-acetamide 
• 90515-49-4 N-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-3,4,5-trimethoxy-benzamide 

Relevant articles and documents

Targeting adenosine receptors with coumarins: Synthesis and binding activities of amide and carbamate derivatives

Objectives With the aim of finding the structural features governing binding activity and selectivity against adenosine receptors (ARs), several 3-subtituted coumarins with amide (compounds 3-6) and carbamate (7-9) functions were synthesized. To study its possible influence on the binding activity and selectivity, a hydroxyl substituent was also introduced at position 4 of the coumarin moiety. Methods A new series of coumarins (3-9) were synthesized and evaluated by radioligand binding studies towards ARs. Key findings None of the 4-hydroxy derivatives (4, 8 and 9) showed binding affinity for any of the ARs. None of the compounds interacted with the hA2B AR (Ki > 100 000 nm). Compounds 3, 5, 6 and 7 had different activity profiles with dissimilar binding affinity and selectivity towards human A1, A 2A and A3 ARs. Conclusions The most remarkable derivative is compound 7, which presents the best affinity and selectivity for the A 3 adenosine receptor (Ki = 5500 nm).

A convergent paired electrochemical synthesis of new heterocyclic compounds. Reaction of benzoquinones with 3-Amino-4-hydroxycoumarin

Electrochemical oxidation of catechols (1) has been studied in the presence of cathodically generated 3-amino-4- hydroxycoumarin (3a) as a nucleophile in aqueous solutions, using cyclic voltammetry and controlled-potential coulometry. The results indicate that the o-benzoquinones derived from catechols (1) participate in Michael addition reaction with 3-amino-4- hydroxycoumarin (3a) to form the corresponding new heterocyclic compounds (7) (oxidized form of coumestan derivatives). The electrochemical process consists of a multi-step including (a) cathodic reduction of 4-hydroxy-3-nitrocoumarin (3) to 3-amino-4- hydroxycoumarin (3a), (b) anodic oxidation of catechols (1) to related o-benzoquinone (2), (c) the Michael addition reaction of 3- amino-4-hydroxycoumarin (3a) to o-benzoquinone (2), and (d) anodic oxidation of formed adduct. The paired electrochemical synthesis of compounds 7a and 7b has been successfully performed in a one-pot process at carbon rods as working and counter electrodes in an undivided cell.

Pseudo three-component approach to coumarin-annulated azepines: Synthesis of coumarin[3,4-: B] azepines

A series of coumarin-annulated azepines were synthesized via acid-catalyzed condensation of 3-amino-4-hydroxycoumarin with two equivalents of substituted acetophenones in toluene with moderate to good yields. A plausible mechanism for this pseudo three-component reaction was proposed.

4 - hydroxy coumarin - 3 - sheaff alkali derivatives and their use for treating Alzheimer's disease

The invention relates to the field of medicinal chemistry, in particular to a 4-hydroxycoumarin-3-Schiff base compound (I). Pharmacodynamic experiments prove that the compound is a multifunctional monoamine oxidase (MAO) inhibitor, has better effects of i