110254-63-2

Basic information

• Product Name: 4-CHLORO-1-PHENYL-1,2-DIHYDROQUINOLIN-2-ONE
• Synonyms: AKOS BBS-00003070;4-CHLORO-1-PHENYL-1H-QUINOLIN-2-ONE;4-CHLORO-1-PHENYLQUINOLIN-2(1H)-ONE;4-CHLORO-1-PHENYL-1,2-DIHYDROQUINOLIN-2-ONE;AURORA KA-3939
• CAS NO: 110254-63-2
• Molecular Formula: C₁₅H₁₀ClNO
• Molecular Weight: 255.7
• Mol File: 110254-63-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 138-141 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 399.4°Cat760mmHg
• Flash Point: 195.3°C
• Appearance: /
• Density: 1.35g/cm³
• Vapor Pressure: 1.38E-06mmHg at 25°C
• Refractive Index: 1.686
• PKA: -5.06±0.40(Predicted)
• CAS DataBase Reference: 4-CHLORO-1-PHENYL-1,2-DIHYDROQUINOLIN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-1-PHENYL-1,2-DIHYDROQUINOLIN-2-ONE(110254-63-2)
• EPA Substance Registry System: 4-CHLORO-1-PHENYL-1,2-DIHYDROQUINOLIN-2-ONE(110254-63-2)

Safety Data

• Hazardous Substances Data: 110254-63-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H10ClNO/c16-13-10-15(18)17(11-6-2-1-3-7-11)14-9-5-4-8-12(13)14/h1-10H

Upstream product

• 122-39-4 diphenylamine 
• 14994-75-3 4-hydroxy-1-phenylquinolin-2(1H)-one 

Downstream Products

• 166191-74-8 (2-Oxo-1-phenyl-1,2-dihydro-quinolin-4-ylsulfanyl)-acetic acid 
• 166191-80-6 3-Hydroxy-5-phenyl-5H-thieno[3,2-c]quinolin-4-one 

Relevant articles and documents

Symmetrical bisquinolones via metal-catalyzed cross-coupling and homocoupling reactions

Functionalized 4,4′-bisquinolones can be efficiently synthesized by microwave-assisted palladium(0)-catalyzed one-pot borylation/Suzuki cross-coupling reactions or via nickel(0)-mediated homocouplings of 4-chloroquinolin-2(1H)-one precursors. Both methods are also applicable to other types of symmetrical biaryls.

Novel 4-(piperazin-1-yl)quinolin-2(1H)-one bearing thiazoles with antiproliferative activity through VEGFR-2-TK inhibition

A new series of 2-(4-(2-oxo-1,2-dihydroquinolin-4-yl)piperazin-1-yl)-N-(4-phenylthiazol-2-yl)acetamide derivatives were synthesized and evaluated for anticancer activity. All target compounds showed anticancer activity higher than that of their 2-oxo-4-piperazinyl-1,2-dihydroquinolin-2(1H)-one precursors. Multidose testing of target compounds was performed against breast cancer T-47D cell line. Five compounds showed higher cytotoxic activity than Staurosporine. The dihalogenated derivative showed the best cytotoxic activity with IC50 2.73 ± 0.16 μM. In addition, the VEGFR-2 inhibitory activity of all synthetic compounds was evaluated. Two compounds of 6-fluoro-4-(piperazin-1-yl)quinolin-2(1H)-ones showed inhibitory activity comparable to sorafenib with IC50 46.83 ± 2.4, 51.09 ± 2.6 and 51.41 ± 2.3 nM, respectively. The cell cycle analysis of two compounds namely, 2-(4-(6-fluoro-2-oxo-1,2-dihydroquinolin-4-yl)piperazin-1-yl)-N-(4-phenylthiazol-2-yl)acetamide and N-(4-(4-chlorophenyl)thiazol-2-yl)-2-(4-(2-oxo-1-phenyl-1,2-dihydroquinolin-4-yl)piperazin-1-yl)acetamide revealed that the arrest of cell cycle occurred at S phase. In apoptosis assay, the same two compounds were able to induce significant levels of early and late apoptosis. In a similar manner to Sorafenib, docking of target compounds with VEGFR-2 protein 4ASD showed HB with Cys919 in hinge region of enzyme and HB with both Glu885 and Asp1046 in gate area. Using SwissADME, all target compounds were predicted to be highly absorbed from gastrointestinal tract with no BBB permeability. It is clear that the two compounds are promising antiproliferative candidates that require further optimization.

Methods for the Synthesis of 4-Azido-2(1H)-quinolones

4-Hydroxy-2-quinolones 1 are generally found to be converted to the 4-azidocompounds 3 via the 4-chloroquinolones 2, the 4-tosyloxyquinolones 6, or the 4-aminoquinolones 4, respectively.Choice of the reaction conditions and yields depend on the substituen