66134-57-4

Basic information

• Product Name: 3-ACETYL-1-ETHYL-4-HYDROXY-2(1H)-QUINOLINONE
• Synonyms: AKOS BBS-00001236;3-ACETYL-1-ETHYL-4-HYDROXY-2(1H)-QUINOLINONE;AURORA KA-4041;3-Acetyl-1-ethyl-4-hydroxy-1H-quinolin-2-one
• CAS NO: 66134-57-4
• Molecular Formula: C₁₃H₁₃NO₃
• Molecular Weight: 231.25
• Mol File: 66134-57-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 366.4°Cat760mmHg
• Flash Point: 175.4°C
• Appearance: /
• Density: 1.292g/cm³
• Vapor Pressure: 5.17E-06mmHg at 25°C
• Refractive Index: 1.607
• CAS DataBase Reference: 3-ACETYL-1-ETHYL-4-HYDROXY-2(1H)-QUINOLINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ACETYL-1-ETHYL-4-HYDROXY-2(1H)-QUINOLINONE(66134-57-4)
• EPA Substance Registry System: 3-ACETYL-1-ETHYL-4-HYDROXY-2(1H)-QUINOLINONE(66134-57-4)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• Hazardous Substances Data: 66134-57-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H13NO3/c1-3-14-10-7-5-4-6-9(10)12(16)11(8(2)15)13(14)17/h4-7,17H,3H2,1-2H3

Upstream product

• 68556-21-8 C₁₀H₁₁NO₂ 
• 134-20-3 2-carbomethoxyaniline 
• 17318-49-9 methyl 2-(ethylamino)benzoate 
• 103-69-5 N-ethyl-N-phenylamine 
• 231935-88-9 3-acetyl-4-hydroxy-6-ethylpyrano<3,2-c>quinoline-2,5(6H)-ione 
• 161185-28-0 6-ethyl-4-hydroxy-2,5-dioxo-5,6-dihydro-2H-pyrano[3,2-c]quinoline 

Downstream Products

• 1063696-22-9 (2E)-1-(1-ethyl-4-hydroxyquinolin-2(1H)-one-3-yl)-3-(4-chlorophenyl)-2-propen-1-one 
• 54675-30-8 1-ethyl-4-hydroxy-1H-quinolin-2-one 

Relevant articles and documents

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.

Studies with polyfunctionally substituted heteroarenes: New synthesis of benzo [c] quinolinones and pyrano [3,2-c] quinoline derivatives

Nitration, bromination and acetylation of 4 - hydroxypyranoquinolines 1 yielded 3-nitro-, 3-bromo, and 3-acetylpyranoquinolines 3,5,8. Hyrolysis of 3, 5 and 8 with 2N NaOH afforded 3-nitroacetyl, 3-bromoacetyl and 3- acetylquinolines 4, 6 and 7 respectively. Formylation of 1 or 7 gave 3- formyl pyranoquinolines 9a-c. Reactions of 8 with 2 afforded benzo [c] quinolines 11 and 12. Treatment of 1, 24 or 7 with the ylidene 21 resulted in the formation of pyranoquinolines 25.