83520-73-4

Basic information

• Product Name: 3-(1H-Benzimidazol-2-yl)-2(1H)-quinolinone
• Synonyms: 3-(1H-Benzimidazol-2-yl)-2(1H)-quinolinone
• CAS NO: 83520-73-4
• Molecular Formula: C16H11N3O
• Molecular Weight: 261
• Mol File: 83520-73-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 324-325℃ (DEC.)
• Appearance: /
• Density: 1.375
• CAS DataBase Reference: 3-(1H-Benzimidazol-2-yl)-2(1H)-quinolinone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(1H-Benzimidazol-2-yl)-2(1H)-quinolinone(83520-73-4)
• EPA Substance Registry System: 3-(1H-Benzimidazol-2-yl)-2(1H)-quinolinone(83520-73-4)

Safety Data

• Hazardous Substances Data: 83520-73-4(Hazardous Substances Data)

Upstream product

• 103-84-4 Acetanilid 
• 73568-25-9 2-chloro-3-quinoline carboxaldehyde 
• 91301-03-0 3-formyl-2-quinolone 
• 95-54-5 1,2-diamino-benzene 
• 51-17-2 benzoimidazole 
• 939-16-2 3-bromoquinolin-2-one 
• 14741-71-0 ethyl (1H-benzimidazol-2-yl)acetate 
• 529-23-7 o-aminobenzaldehyde 

Relevant articles and documents

A general Pd/Cu-catalyzed C-H heteroarylation of 3-bromoquinolin-2(1H)-ones

3-(Heteroaryl)quinolin-2(1H)-ones were synthesized in good to excellent yields using a bimetallic catalytic system through the C-H heteroarylation strategy. Starting from 3-bromoquinolin-2(1H)-ones, various azoles have been successfully used. In all cases, the reactions take place rapidly in dioxane and efficiently proceed in the presence of a bimetallic Pd(OAc)2/CuI as the catalyst, PPh3 as the ligand and LiOtBu or KOAc as the base. This journal is

Design, synthesis and pharmacological evaluation of new 3-(1H-benzimidazol-2-yl)quinolin-2(1H)-one derivatives as potential antitumor agents

A series of new 3-(1H-benzimidazol-2-yl)quinolin-2(1H)-one derivatives (5a1?5d6) were designed and synthesized as antitumor agents. In vitro antitumor assay results showed that some compounds exhibited moderate to high inhibitory activity against HepG2, SK-OV-3, NCI-H460 and BEL-7404 tumor cell lines, and most compounds exhibited much lower cytotoxicity against the HL-7702 normal cell line compared to 5-FU and cisplatin. In vivo antitumor assay results demonstrated that 5a3 exhibited effective inhibition on tumor growth in the NCI-H460 xenograft mouse model and that 5d3 displayed excellent antiproliferative activity in the BEL-7402 xenograft model. These results suggested that both 5a3 and 5d3 could be used as anticancer drug candidates. Mechanistic studies suggested that compounds 5a3 and 5d3 exerted their antitumor activity by up-regulation of Bax, intracellular Ca2+ release, ROS generation, downregulation of Bcl-2, activation of caspase-9 and caspase-3 and subsequent cleavage of PARP, inhibition of CDK activity and activation of the p53 protein.

A simple one-pot synthesis of new imidazol-2-yl-lh-quinolin-2-ones from the direct reaction of 2-chloroquinolin-3-carbaldehyde with aromatic o-diamines

An alternative and general one-pot synthesis of a library of novel imidazol-2-yl-1H-quinolin-2-one derivatives was performed in 70 % aqueous acetic acid by the direct reaction of 2-chloroquinolin-3-carbaldehyde with aromatic o-diamines. Experiments showed that adding Amberlyst (20% w/w) to the reaction media increased both the speed of reaction as well as the yield of products. Both DFT theoretical calculations and X-ray diffraction studies confirmed the proposed structures and the more stable conformation of the obtained products, Antitumor studies against sixty different cancer cell lines showed the potential of these kinds of compounds.