26138-64-7

Basic information

• Product Name: 3-acetyl-4-hydroxy-2-quinolone
• Synonyms: 3-acetyl-4-hydroxy-2-quinolone;3-Acetyl-2,4-dihydroxyquinoline;3-Acetyl-4-hydroxyquinolin-2(1H)-one;3-Acetyl-4-hydroxyquinolin-2(1H)
• CAS NO: 26138-64-7
• Molecular Formula: C₁₁H₉NO₃
• Molecular Weight: 203.19406
• EINECS: 247-476-8
• Mol File: 26138-64-7.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 362.6°Cat760mmHg
• Flash Point: 173.1°C
• Appearance: /
• Density: 1.388g/cm³
• Vapor Pressure: 6.8E-06mmHg at 25°C
• Refractive Index: 1.633
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 3-acetyl-4-hydroxy-2-quinolone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-acetyl-4-hydroxy-2-quinolone(26138-64-7)
• EPA Substance Registry System: 3-acetyl-4-hydroxy-2-quinolone(26138-64-7)

Safety Data

• Hazardous Substances Data: 26138-64-7(Hazardous Substances Data)

Usage

General Description

3-acetyl-4-hydroxy-2-quinolone is a chemical compound with the molecular formula C11H9NO3. It is a derivative of 4-hydroxy-2-quinolone and is known for its biological activities, including antibiotic, antifungal, and antitumor properties. 3-acetyl-4-hydroxy-2-quinolone has been studied for its potential use in pharmaceutical applications due to its ability to inhibit the growth of various microorganisms. It has also shown promise in cancer research, with studies indicating its potential for use in cancer therapy. 3-acetyl-4-hydroxy-2-quinolone is a highly versatile compound with a wide range of potential applications in the field of medicine and drug development.

InChI:InChI=1/C11H9NO3/c1-6(13)9-10(14)7-4-2-3-5-8(7)12-11(9)15/h2-5H,1H3,(H2,12,14,15)

Upstream product

• 70254-43-2 4-Hydroxy-2-quinolone 
• 86119-84-8 phosphoric acid 
• 64-19-7 acetic acid 
• 87-25-2 2-ethoxycarbonylaniline 
• 81937-41-9 Methyl N-acetoacetylanthranilate 
• 89-52-1 o-acetylamino-benzoic acid 
• 141-97-9 ethyl acetoacetate 
• 134-20-3 2-carbomethoxyaniline 
• 118-92-3 anthranilic acid 
• 102-01-2 N-phenylacetoacetamide 
• 145508-18-5 2-[bis(methylsulfanyl)methylidene]-3-oxo-N-phenylbutanamide 
• 525-76-8 2-methyl-4-oxo-3,1-benzoxazine 
• 41470-88-6 2-ethoxy-4H-benzo[d][1,3]oxazin-4-one 
• 477868-31-8 2-(2-Acetylamino-benzoyl)-3-oxo-butyric acid ethyl ester 

Downstream Products

• 101569-81-7 3-[1-(2-phenylhydrazono)ethyl]-4-hydroxyquinolin-2(1H)-one 
• 54289-76-8 3-acetyl-4-hydroxy-1-methyl-2(1H)-quinolone 
• 1190695-30-7 C₂₇H₂₆N₄O₅ 
• 1478449-20-5 C₁₉H₁₆N₂O₃ 
• 4694-51-3 7-methyldibenzo[c,f][2,7]naphthyridin-6(5H)-one 
• 1478449-16-9 3-(1-(phenylimino)ethyl)-2,4-dihydroxyquinoline 
• 1478449-56-7 3-(1-(4-methylphenylimino)ethyl)-2,4-dihydroxyquinoline 
• 1478449-58-9 3-(1-(2-methoxyphenylimino)ethyl)-2,4-dihydroxyquinoline 
• 1478449-60-3 3-(1-(4-methoxyphenylimino)ethyl)-2,4-dihydroxyquinoline 

Relevant articles and documents

Novel quinolinone–pyrazoline hybrids: synthesis and evaluation of antioxidant and lipoxygenase inhibitory activity

Abstract: The present project deals with the investigation of structure–activity relationship of several quinolinone–chalcone and quinolinone–pyrazoline hybrids, in an effort to discover promising antioxidant and anti-inflammatory agents. In order to accomplish this goal, four bioactive hybrid quinolinone–chalcone compounds (8a–8d) were synthesized via an aldol condensation reaction, which were then chemically modified, forming fifteen new pyrazoline analogues (9a–9o). All the synthesized analogues were in vitro evaluated in terms of their antioxidant and soybean lipoxygenase (LOX) inhibitory activity. Among all the pyrazoline derivatives, compounds 9b and 9m were found to possess the best combined activity, whereas 9b analogue exhibited the most potent LOX inhibitory activity, with IC50 value 10?μM. The in silico docking results revealed that the synthetic pyrazoline analogue 9b showed high AutoDock Vina score (? 10.3?kcal/mol), while all the tested derivatives presented allosteric interactions with the enzyme. Graphic Abstract: [Figure not available: see fulltext.]

Synthesis and Evaluation of 4-Hydroxycoumarin Imines as Inhibitors of Class II Myosins

Inhibitors of muscle myosin ATPases are needed to treat conditions that could be improved by promoting muscle relaxation. The lead compound for this study ((3-(N-butylethanimidoyl)ethyl)-4-hydroxy-2H-chromen-2-one; BHC) was previously discovered to inhibit skeletal myosin II. BHC and 34 analogues were synthesized to explore structure-activity relationships. The properties of analogues, including solubility, stability, and toxicity, suggest that the BHC scaffold may be useful for developing therapeutics. Inhibition of actin-activated ATPase activity of fast skeletal and cardiac muscle myosin II, inhibition of skeletal muscle contractility ex vivo, and slowing of in vitro actin-sliding velocity were measured. Several analogues with aromatic side arms showed improved potency (half-maximal inhibitory concentration (IC50) 1 μM) and selectivity (≥12-fold) for skeletal myosin versus cardiac myosin compared to BHC. Several analogues blocked neurotransmission, suggesting that they are selective for nonmuscle myosin II over skeletal myosin. Competition and molecular docking studies suggest that BHC and blebbistatin bind to the same site on myosin.

Synthesis and anti-parasitic activity of a novel quinolinone-chalcone series

A series of novel quinolinone-chalcone hybrids and analogues were designed, synthesized and their biological activity against the mammalian stages of Trypanosoma brucei and Leishmania infantum evaluated. Promising molecular scaffolds with significant microbicidal activity and low cytotoxicity were identified. Quinolinone-chalcone 10 exhibited anti-parasitic properties against both organisms, being the most potent anti-L. infantum agent of the entire series (IC50 value of 1.3 ± 0.1 μM). Compounds 4 and 11 showed potency toward the intracellular, amastigote stage of L. infantum (IC50 values of 2.1 ± 0.6 and 3.1 ± 1.05 μM, respectively). Promising trypanocidal compounds include 5 and 10 (IC 50 values of 2.6 ± 0.1 and 3.3 ± 0.1 μM, respectively) as well as 6 and 9 (both having IC50 values of 5 μM). Chemical modifications on the quinolinone-chalcone scaffold were performed on selected compounds in order to investigate the influence of these structural features on antiparasitic activity.