174636-77-2

Basic information

• Product Name: 4-QUINOLINECARBONYL CHLORIDE,6-CHLORO-2-PHENYL-
• Synonyms: 4-QUINOLINECARBONYL CHLORIDE,6-CHLORO-2-PHENYL-;6-chloro-2-phenyl-4-quinolinecarbonyl chloride
• CAS NO: 174636-77-2
• Molecular Formula: C16H9Cl2NO
• Molecular Weight: 302.16
• Mol File: 174636-77-2.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-QUINOLINECARBONYL CHLORIDE,6-CHLORO-2-PHENYL-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-QUINOLINECARBONYL CHLORIDE,6-CHLORO-2-PHENYL-(174636-77-2)
• EPA Substance Registry System: 4-QUINOLINECARBONYL CHLORIDE,6-CHLORO-2-PHENYL-(174636-77-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 174636-77-2(Hazardous Substances Data)

Upstream product

• 6633-62-1 6-chloro-2-phenylquinoline-4-carboxylic acid 
• 106-47-8 4-chloro-aniline 
• 65798-06-3 N-(4-chlorophenyl)-2-(hydroxyimino)ethanamide 
• 17630-76-1 5-chloroindole 2,3-dione 
• 98-86-2 acetophenone 

Relevant articles and documents

Design, synthesis and biological evaluation of 2-phenylquinoline-4-carboxamide derivatives as a new class of tubulin polymerization inhibitors

A novel series of 2-phenylquinoline-4-carboxamide derivatives was synthesized, characterized and evaluated for its antiproliferative activity against five cancer cell lines, Hela, SK-OV-3, HCT116, A549 and MDA-MB-468, and a normal human fetal lung fibroblastic cell line, MRC-5. Among them, compound 7b displayed potent cytotoxic activity in vitro against SK-OV-3 and HCT116 cell lines with IC50 values of 0.5 and 0.2 μM, respectively. In general, the antiproliferative activity was correlated with the binding property of the colchicine binding site and inhibitory effect on tubulin polymerization. In addition, immunofluorescence and flow cytometry analysis revealed that selected compounds caused disruption of the mitotic spindle assembly and G2/M phase arrest of the cell cycle, which correlated with proliferation inhibitory activity. Molecular docking analysis demonstrated the interaction of 7b at the colchicine binding site of tubulin. These results indicate these compounds are promising inhibitors of tubulin polymerization for the potent treatment of cancer.

Design, synthesis and evaluation of quinoline-based small molecule inhibitor of stat3

As STAT3 has been validated as an anticancer target, its inhibitors have been shown to possess therapeutic promise for the treatment of human cancers. To identify novel and selective STAT3 inhibitors, a virtual screening based on the STAT3 SH2 domain was performed and a small molecule, 2-phenylquinoline-4- carboxylic acid (5a), with an inhibition constant Ki value of 17.53 iM to STAT3 was discovered. On this basis, the derivatives of 5a including esters, amides and dimers were synthesized. The bioactivity and inhibitory selectivity of the derivatives were assayed using human breast cancer cell lines, MDA-MB-468 and MCF-7. Among the derivatives, 5c and 9b showed the most potent inhibitory activity with a good selectivity, and also inhibited STAT3 protein level of MDA-MB-468 cells. The results demonstrated a successful application of virtual screening for lead discovery. Compound 9b might be an effective STAT3 inhibitor lead for the further development of antitumor agents.