4590-52-7

Basic information

• Product Name: NISTC4590527
• Synonyms: NISTC4590527;7-Fluoro-3,4-dihydroquinolin-2(1H)-one;7-fluoro-3,4-dihydro-2(1H)-Quinolinone;7-Fluoro-3,4-dihydroquinolin-2(1H);2(1H)-Quinolinone, 7-fluoro-3,4-dihydro-
• CAS NO: 4590-52-7
• Molecular Formula: C₉H₈FNO
• Molecular Weight: 165.1643232
• Mol File: 4590-52-7.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 305.8°Cat760mmHg
• Flash Point: 138.7°C
• Appearance: /
• Density: 1.241g/cm³
• Vapor Pressure: 0.000804mmHg at 25°C
• Refractive Index: 1.542
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.01±0.20(Predicted)
• CAS DataBase Reference: NISTC4590527(CAS DataBase Reference)
• NIST Chemistry Reference: NISTC4590527(4590-52-7)
• EPA Substance Registry System: NISTC4590527(4590-52-7)

Safety Data

• Hazardous Substances Data: 4590-52-7(Hazardous Substances Data)

Usage

Uses

7-Fluoro-3,4-dihydroquinolin-2(1H)-one is a useful reagent in the multicomponent one-pot synthesis of 3,4-dihydroquinolinones.

InChI:InChI=1/C9H8FNO/c10-7-3-1-6-2-4-9(12)11-8(6)5-7/h1,3,5H,2,4H2,(H,11,12)

Upstream product

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• 313545-72-1 2-chloro-4-fluorophenylboronic acid 
• 364-78-3 2-nitro-4-fluoroaniline 
• 231297-56-6 methyl (E)-3-(4′-fluoro-2′-nitrophenyl)acrylate 

Downstream Products

• 939758-75-5 7-fluoro-1,2,3,4-tetrahydroquinoline 
• 148136-14-5 7-fluoroquinolin-2(1H)-one 
• 1384850-32-1 3-(7-fluoro-1,2,3,4-tetrahydroquinolin-1-yl)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid 
• 1384850-72-9 methyl 3-(7-fluoro-1,2,3,4-tetrahydroquinolin-1-yl)-2-(4-fluorophenyl)quinoxaline-6-carboxylate 
• 1156389-00-2 6-bromo-7-fluoro-3,4-dihydroquinolin-2(1H)-one 

Relevant articles and documents

Dehydrogenative and Redox-Neutral N-Heterocyclization of Aminoalcohols Catalyzed by Manganese Pincer Complexes

A new manganese catalyzed heterocyclization of aminoalcohols has been accomplished. A wide range of heterocycles were synthesized, including 1,2,3,4-tetrahydroquinolines, dihydroquinolinones, and 2,3,4,5-tetrahydro-1H-benzo[b]azepines. The reaction is performed under mild reaction conditions using air and moisture stable manganese catalysts. The desired heterocycles were obtained in good to excellent yields.

Discovery of tetrahydroquinolines and benzomorpholines as novel potent RORγt agonists

The retinoic acid receptor-related orphan receptor γt (RORγt) is an important nuclear receptor that regulates the differentiation of Th17 cells and production of interleukin 17(IL-17). RORγt agonists increase basal activity of RORγt and could provide a potential approach to cancer immunotherapy. Herein, hit compound 1 was identified as a weak RORγt agonist during in-house library screening. Changes in LHS core of 1 led to the identification of tetrahydroquinoline compound 6 as a partial RORγt agonist (max. act. = 39.3%). Detailed structure-activity relationship on substituent of the LHS core, amide linker and RHS arylsulfonyl moiety was explored and a novel series of tetrahydroquinolines and benzomorpholines was discovered as potent RORγt agonists. Tetrahydroquinoline compound 8g (EC50 = 8.9 ± 0.4 nM, max. act. = 104.5%) and benzomorpholine compound 9g (EC50 = 7.5 ± 0.6 nM, max. act. = 105.8%) were representative compounds with high RORγt agonistic activity in dual FRET assay, and they showed good activity in cell-based Gal4 reporter gene assay and Th17 cell differentiation assay (104.5% activation at 300 nM of 8g; 59.4% activation at 300 nM of 9g). The binding modes of 8g and 9g as well as the two RORγt inverse agonists accidentally discovered were also discussed.

TETRAHYDROQUINOLINO DERIVATIVES FOR THE TREATMENT OF METASTATIC AND CHEMORESISTANT CANCERS

Disclosed herein are compounds of Structural Formula I. Compounds of Structural Formula I inhibit aldehyde dehydrogenase isoform Ia3 (ALDHIa3) and are useful for treating cancer, for example, metastatic or chemoresistant cancer, such as metastatic cancer resistant to chemotherapy. Also disclosed herein are compositions comprising compounds of Structural Formula I and uses of compounds of Structural Formula I for treating cancer, for example, metastatic or chemoresistant cancer.