1333500-26-7

Basic information

• Product Name: 4-hydroxy-3-[3-(4-nitrophenyl)-1-oxo-2-propen-1-yl]-2(1Η)-quinolinone
• Synonyms: 4-hydroxy-3-[3-(4-nitrophenyl)-1-oxo-2-propen-1-yl]-2(1Η)-quinolinone
• CAS NO: 1333500-26-7
• Molecular Weight: 336.304
• Mol File: 1333500-26-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4-hydroxy-3-[3-(4-nitrophenyl)-1-oxo-2-propen-1-yl]-2(1Η)-quinolinone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-hydroxy-3-[3-(4-nitrophenyl)-1-oxo-2-propen-1-yl]-2(1Η)-quinolinone(1333500-26-7)
• EPA Substance Registry System: 4-hydroxy-3-[3-(4-nitrophenyl)-1-oxo-2-propen-1-yl]-2(1Η)-quinolinone(1333500-26-7)

Safety Data

• Hazardous Substances Data: 1333500-26-7(Hazardous Substances Data)

Upstream product

• 477868-31-8 2-(2-Acetylamino-benzoyl)-3-oxo-butyric acid ethyl ester 
• 118-92-3 anthranilic acid 
• 525-76-8 2-methyl-4-oxo-3,1-benzoxazine 
• 134-20-3 2-carbomethoxyaniline 
• 81937-41-9 Methyl N-acetoacetylanthranilate 
• 26138-64-7 4-hydroxy-3-acetyl-1H-quinoline-2-one 
• 555-16-8 4-nitrobenzaldehdye 

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.

Solvent-free protocol for stereo selective crossed aldol condensation assisted by solid acid catalyst

A highly efficient, inexpensive, recyclable, green and solvent free protocol has been developed for crossed-aldol reaction. SiO2-OSO 3H has been found to be an efficient catalyst for the synthesis of 4-hydroxy-3-(3-phenyl-acryloyl)-1H-quinoline-2-one derivatives 3(a-i) from 4-hydroxy-3-acetyl-1H-quinoline-2-one (1) and substituted benzaldehydes 2(a-i). Reactions occurred smoothly with variations of the substituents. The reagent can be reused for five cycles with out sacrificing the yields and activity. This method is simple, convenient and the target compounds are produced in good to excellent yields. Compound 1 can be synthesized by the acylation of methyl anthranilate (4) with acetoacetic ester (5) in refluxing xylene and subsequent Dieckman cyclization of the intermediary 2-methoxycarbonyl anilide (6).