66134-57-4

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

• 161185-28-0 6-ethyl-4-hydroxy-2,5-dioxo-5,6-dihydro-2H-pyrano[3,2-c]quinoline 
• 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 

Downstream Products

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

Relevant academic research and scientific papers

Substituted quinolinones. Part 23. Synthesis of 6-ethyl-4,5-dioxo-5,6- dihydro-4//-pyrano[3,2-c]quinoline-3-carboxaldehyde and its chemical behavior towards hydroxylamine hydrochloride

The synthesis of novel 6-ethyl-4,5-dioxo-5,6-dihydro-4H-pyrano[3,2-c] quinoline-3-carbox-aldehyde is described via Vilsmeier-Haack reaction of 3-acetyl-1-ethyl-4-hydroxyquinolin-2(1H)-one. The reaction of titled aldehyde with hydroxylamine hydrochloride, under different conditions, revealed its distinctive chemical behavior and a variety of products were obtained. This study revealed existence of ring-opening ring-closure (RORC) on treatment with hydroxylamine hydrochloride in both acetic acid and/or ethanolic potassium hydroxide. The structure of the new products was deduced on basis of their analytical and spectral data. ARKAT-USA, Inc.

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.

Syntheses of 3-Acyl-4-hydroxy-2(1H)-quinolones

3-Acyl-4-hydroxy-2(1H)-quinolones 5 are obtained by hydrolytic ring opening and subsequent decarboxylation from the corresponding pyranoquinolin-2,5(6H)-diones 4, which in turn are easily obtained from 1:2 condensation of of anilines 1 with diethyl malonate 2a or 1:1 condensation of diethyl alkyl- or arylmalonates 2b-e with 4-hydroxy-2(1H)-quinolones 3.Nitropyranoquinolinediones 6 furnish after ringopening 3-nitroacetyl-4-hydroxy-2(1H)-quinolones 8.Pyranoquinolines 7 and 9 with acetyl- or aminosubstituents are hydrolyzed during basic ringopening to yield 5.