779-30-6

Basic information

• Product Name: 3-ACETAMIDOCOUMARIN
• Synonyms: 3-(AcetylaMino)couMarin;N-(2-Oxo-2H-1-benzopyran-3-yl)acetaMide;NSC 65873;3-ACETAMIDOCOUMARIN;ACETAMIDOCOUMARIN, 3-;N-(2-Oxo-2H-chromen-3-yl)acetamide;3-ACETAMIDOCOUMARIN 99%;PALMATINE CHLORIDE(P)
• CAS NO: 779-30-6
• Molecular Formula: C₁₁H₉NO₃
• Molecular Weight: 203.19
• EINECS: 125-784-9
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Coumarin;Building Blocks;Coumarins;Heterocyclic Building Blocks;Amines
• Mol File: 779-30-6.mol
• Article Data: 28

Chemical Properties

• Melting Point: 205-207 °C(lit.)
• Boiling Point: 482 °C at 760 mmHg
• Flash Point: 245.3 °C
• Appearance: /
• Density: 1.31 g/cm³
• Vapor Pressure: 1.89E-09mmHg at 25°C
• Refractive Index: 1.604
• CAS DataBase Reference: 3-ACETAMIDOCOUMARIN(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ACETAMIDOCOUMARIN(779-30-6)
• EPA Substance Registry System: 3-ACETAMIDOCOUMARIN(779-30-6)

Safety Data

• Safety Statements: S22:Do not inhale dust.; S24/25:Avoid contact with skin and eyes.
• WGK Germany: 3
• Hazardous Substances Data: 779-30-6(Hazardous Substances Data)

Usage

Uses

3-ACETAMIDOCOUMARIN is a 3-substituted couramin derivative with antioxidant activity. It is used as a matrix in MALDI TOF-MS analysis of polyethylene glycol samples.

InChI:InChI=1/C11H9NO3/c1-7(13)12-9-6-8-4-2-3-5-10(8)15-11(9)14/h2-6H,1H3,(H,12,13)

Upstream product

• 91137-46-1 3-(1-hydroxyimino-ethyl)-coumarin 
• 10026-13-8 phosphorus pentachloride 
• 7719-12-2 phosphorus trichloride 
• 60-35-5 acetamide 
• 939-18-4 3-bromo-2H-chromen-2-one 
• 1635-31-0 aminocoumarine 
• 75-36-5 acetyl chloride 
• 1906-82-7 ethyl acetamidoacetate 
• 90-02-8 salicylaldehyde 
• 3949-36-8 3-acetylcoumarin 
• 543-24-8 N-acetylglycine 
• 24474-93-9 2-methyl-4H-oxazol-5-one 

Downstream Products

• 1635-31-0 aminocoumarine 
• 5818-89-3 Chromannedione-2,3 
• 6803-09-4 3-(2'-hydroxyphenyl)-2-hydroxypropanoic acid 
• 709-16-0 2-hydroxy-phenylalanine 
• 1414381-87-5 3-(2-chlorophenyl)-1-phenyl-5H-chromeno[3,4-b]pyridin-5-one 
• 1414381-85-3 3-(4-bromophenyl)-1-phenyl-5H-chromeno[3,4-b]pyridin-5-one 
• 1070987-62-0 3-(4-nitrophenyl)-1-phenyl-5H-chromeno[3,4-b]pyridin-5-one 
• 1414381-90-0 4-(5-oxo-1-phenyl-5H-chromeno[3,4-b]pyridin-3-yl)benzonitrile 

Relevant articles and documents

A convenient and expeditious synthesis of 3-(N-substituted) aminocoumarins via palladium-catalyzed Buchwald-Hartwig coupling reaction

A convenient protocol for the rapid and efficient synthesis of 3-(N-substituted) aminocoumarins is described. The synthetic route developed involves the Pd-catalyzed C-N coupling reaction from readily available 3-bromocoumarin derivatives in the presence of the catalytic system Pd(OAc)2/Xantphos. Under these conditions, a series of nucleophiles including amides, sulfonamides, carbamates and functionalized amines, have been successfully reacted to afford the coupling products in fair to good yields.

Mild and highly efficient deacetylation of acetamido and acetoxy coumarins: A convenient and expeditious synthesis of substituted 3-aminocoumarins

A convenient protocol for efficient and cost-effective method for synthesis of substituted 3-aminocoumarins has been developed. The synthetic route involves expeditious and fast quantitative deacetylation of readily available acetamido derivative under anhydrous acidic conditions, employing thionyl chloride in methanol, without formation of undesired substituted 3-hydroxycoumarins. The method is suitable for derivatives bearing electron-donating as well as electron-withdrawing groups at position 7 of the coumarin scaffold. Under these conditions, a series of acetoxy substituted 3-dialkylaminocoumarins has been also successfully deacetylated to afford easily isolable corresponding hydroxy derivatives in high yields.

Rational design, synthesis and biological evaluation of novel multitargeting anti-AD iron chelators with potent MAO-B inhibitory and antioxidant activity

A series of (3-hydroxypyridin-4-one)-coumarin hybrids were developed and investigated as potential multitargeting candidates for the treatment of Alzheimer's disease (AD) through the incorporation of iron-chelating and monoamine oxidase B (MAO-B) inhibition. This combination endowed the hybrids with good capacity to inhibit MAO-B as well as excellent iron-chelating effects. The pFe3+ values of the compounds were ranging from 16.91 to 20.16, comparable to more potent than the reference drug deferiprone (DFP). Among them, compound 18d exhibited the most promising activity against MAO-B, with an IC50 value of 87.9 nM. Moreover, compound 18d exerted favorable antioxidant activity, significantly reversed the amyloid-β1-42 (Aβ1-42) induced PC12 cell damage. More importantly, 18d remarkably ameliorated the cognitive dysfunction in a scopolamine-induced mice AD model. In brief, a series of hybrids with potential anti-AD effect were successfully obtained, indicating that the design of iron chelators with MAO-B inhibitory and antioxidant activities is an attractive strategy against AD progression.