75483-04-4

Usage

Uses

Used in Antioxidant Response Element (ARE) Activation:
4-Chloro-1,2-dihydro-3-(ethoxycarbonyl)-1-methyl-2-oxoquinoline is used as an ARE activator for activating Nrf2 by covalently modifying Keap1, a negative regulator of Nrf2. This modification disrupts the ability of Keap1 to serve as an adaptor for the Cul3-Keap1 ubiquitin ligase complex, thereby stabilizing and inducing transcriptional activation of Nrf2.
Used in Cellular Physiology Research:
4-Chloro-1,2-dihydro-3-(ethoxycarbonyl)-1-methyl-2-oxoquinoline is used as a pharmacological tool for probing the involvement of Nrf2 in cellular physiology. Its cell permeable property allows for easy study of its effects on cells.

References

1) Hur?et al. (2010),?A small-molecule inducer of the antioxidant response element; Chem. Biol.,?17?537

InChI:InChI=1/C13H12ClNO3/c1-3-18-13(17)10-11(14)8-6-4-5-7-9(8)15(2)12(10)16/h4-7H,3H2,1-2H3

Upstream product

• 99429-64-8 ethyl ester of 4-chloro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 
• 118-48-9 isatoic anhydride 
• 61352-46-3 6-fluoro-1-methyl-2H-benzo[d][1,3]oxazine-2,4(1H)-dione 
• 321-69-7 5-fluoroisatoic anhydride 
• 85-91-6 Methyl N-methylanthranilate 
• 105-53-3 diethyl malonate 
• 10328-92-4 N-Methylisatoic anhydride 
• 57513-54-9 ethyl 4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate 

Downstream Products

• 1157852-19-1 ethyl 1-methyl-2-oxo-4-tosyl-1,2-dihydroquinoline-3-carboxylate 
• 79966-23-7 2,3,4,5-tetrahydro-5-methyl-3,4-dioxothieno<3,2-c>quinoline-2-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

SUBSTITUTED QUINOLINONYL PIPERAZINE COMPOUNDS USEFUL AS T CELL ACTIVATORS

Disclosed are compounds of Formula (I) or a salt thereof, wherein: R1, R2, R3, R4, R5, R6, and m are defined herein. Also disclosed are methods of using such compounds to inhibit the activi

A novel templates of piperazinyl-1,2-dihydroquinoline-3-carboxylates: Synthesis, anti-microbial evaluation and molecular docking studies

A series of piperazinyl-1,2-dihydroquinoline carboxylates were synthesized by the reaction of ethyl 4-chloro-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylates with various piperazines and their structures were confirmed by 1H NMR, 13C NMR, IR and mass spectral analysis. All the synthesized compounds were screened for their in vitro antimicrobial activities. Further, the in silico molecular docking studies of the active compounds was performed to explore the binding interactions between piperazinyl-1,2-dihydroquinoline carboxylate derivatives and the active site of the Staphylococcus aureus (CrtM) dehydrosqualene synthase (PDB ID: 2ZCQ). The docking studies revealed that the synthesized derivatives showed high binding energies and strong H-bond interactions with the dehydrosqualene synthase validating the observed antimicrobial activity data. Based on antimicrobial activity and docking studies, the compounds 9b and 10c were identified as promising antimicrobial lead molecules. This study might provide insights to identify new drug candidates that target the S. aureus virulence factor, dehydrosqualene synthase.

Synthesis, regioselectivity, and DFT analysis of new antioxidant pyrazolo[4,3-c]quinoline-3,4-diones

The condensation of hydrazine, N-methylhydrazine, and N-phenylhydrazine with ethyl 4-chloro-2-oxo- 1,2-dihydroquinoline-3-carboxylate derivatives has been investigated. As a result, 12 new antioxidant pyrazolo[4,3- c]quinolin-3,4-diones were obtained with good to high yields. When two cross-products could be possible, only one isomer bearing the methyl or the phenyl group at the N1 position is isolated and unequivocally characterized using 1D and 2D NMR techniques, FT-IR, and combustion analyses. DFT analysis of the reaction mechanism was carried out in the Pearson’s hard soft acid base framework, confirming the assigned structure to the observed pyrazolo[4,3-c]quinolin-3,4-diones. These calculations indicate a favored kinetic control for the synthesized pyrazolo[4,3- c]quinolin-3,4-diones compared to its possible regioisomer.

Synthesis of 3,4-disubstituted quinolin-2-(1H)-ones via palladium-catalyzed decarboxylative arylation reactions

The Pd-catalyzed decarboxylative cross-coupling reaction of 4-substituted quinolin-2(1H)-one-3-carboxylic acids with (hetero)aryl halides is described. With palladium(II) bromide and triphenylarsine ligand as the catalyst system, a variety of 4-substituted 3-(hetero)aryl quinolin-2(1 H)-ones and related heterocycles, such as 4-substituted 3-arylcoumarins can be prepared in good to excellent yields. Copyright

4-Hydroxyquinol-2-ones. 86. Synthesis of methyl (ethyl) esters of 1-substituted 4-amino-2-oxoquinoline-3-carboxylic acids

Several variants of the synthesis of esters of 1-N-substituted 4-amino-2-oxoquinoline-3-carboxylic acids have been studied, one of which is recommended as preparative. 2005 Springer Science+Business Media, Inc.

Synthesis of new pyrazolo[4,3-c]quinolin-3-one derivatives and some oxazolo[4,5-c]quinoline-2,4-diones

The new pyrazolo[4,3-c]quinolin-3-one derivatives 3a-c and 6a-c were prepared by the following three steps: first the preparation of ethyl 4- hydroxyquinoline-3-carboxylate derivatives 1 and 4 by reaction of isatoic anhydrides and ethyl malonate and ethyl acetoacetate respectively, then chloration of 1 and 4 with phosphorus oxychloride to give 2 and 5 and finally the condensation of 2 and 5 with hydrazine and its derivatives. In addition, the successful synthesis of oxazolo[4,5-c]quinoline-2,4-diones 9a-f are reported.

Ring Closure and Rearrangement Reactions of 4-Azido-2-oxoquinoline-3-carboxylates and 4-Azidocoumarin-3-carboxylates [1]

4-Azido-2-oxoquinoline-3-carboxylates and 4-azidocoumarin-3-carboxylates 6, which were obtained from the corresponding 4-hydroxy derivatives 1 via 4-tosylates 2 or 4-chloro compounds 4, cyclized upon thermolysis to 3-alkoxyisoxazolo[4,3-c]quinolin-4(5H)-ones or the corresponding coumarins 8, whereas at slightly higher temperatures a 3-O, 4-O-rearrangement took place to give the 4-alkoxy-isoxazolo[4,3-c]-quinolin-3-ones and the corresponding coumarins 9. The necessary reaction conditions could be obtained easily with the help of differential scanning calorimetry.

4-hydroxy-2-quinolones. 30. Alkylation of 1H-2-oxo-3-carbethoxy-4-hydroxyquinoline

A study has been made of the alkylation of 1H-2-oxo-3-carbethoxy-4-hydroxyquinoline by alkyl halides in the presence of inorganic bases. New methods for the synthesis of 1-substituted 2-oxo-3-carbethoxy-4-hydroxyquinolines are examined. 1997 Plenum Publishing Corporation.