20886-09-3

Basic information

• Product Name: 4-(benzyloxy)quinolin-2(1H)-one
• CAS NO: 20886-09-3
• Molecular Formula: C₁₆H₁₃NO₂
• Molecular Weight: 251.2799
• Mol File: 20886-09-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 506.2°C at 760 mmHg
• Flash Point: 259.9°C
• Density: 1.25g/cm³
• Vapor Pressure: 2.28E-10mmHg at 25°C
• Refractive Index: 1.648
• CAS DataBase Reference: 4-(benzyloxy)quinolin-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(benzyloxy)quinolin-2(1H)-one(20886-09-3)
• EPA Substance Registry System: 4-(benzyloxy)quinolin-2(1H)-one(20886-09-3)

Safety Data

• Hazardous Substances Data: 20886-09-3(Hazardous Substances Data)

Upstream product

• 70254-43-2 4-Hydroxy-2-quinolone 
• 100-44-7 benzyl chloride 
• 62-53-3 aniline 

Downstream Products

• 1147107-89-8 C₁₆H₁₂ClNO 

Relevant articles and documents

Synthesis and SAR studies of novel 6,7,8-substituted 4-substituted benzyloxyquinolin-2(1H)-one derivatives for anticancer activity

Background and Purpose 4-Phenylquinolin-2(1H)-one (4-PQ) derivatives can induce cancer cell apoptosis. Additional new 4-PQ analogs were investigated as more effective, less toxic antitumour agents. Experimental Approach Forty-five 6,7,8-substituted 4-substituted benzyloxyquinolin-2(1H)-one derivatives were synthesized. Antiproliferative activities were evaluated using a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazoliun bromide assay and structure-activity relationship correlations were established. Compounds 9b, 9c, 9e and 11e were also evaluated against the National Cancer Institute-60 human cancer cell line panel. Hoechst 33258 and Annexin V-FITC/PI staining assays were used to detect apoptosis, while inhibition of microtubule polymerization was assayed by fluorescence microscopy. Effects on the cell cycle were assessed by flow cytometry and on apoptosis-related proteins (active caspase-3, -8 and -9, procaspase-3, -8, -9, PARP, Bid, Bcl-xL and Bcl-2) by Western blotting. Key Results Nine 6,7,8-substituted 4-substituted benzyloxyquinolin-2(1H)-one derivatives (7e, 8e, 9b, 9c, 9e, 10c, 10e, 11c and 11e) displayed high potency against HL-60, Hep3B, H460, and COLO 205 cancer cells (IC50 50 > 50 μM). Particularly, compound 11e exhibited nanomolar potency against COLO 205 cancer cells. Mechanistic studies indicated that compound 11e disrupted microtubule assembly and induced G2/M arrest, polyploidy and apoptosis via the intrinsic and extrinsic signalling pathways. Activation of JNK could play a role in TRAIL-induced COLO 205 apoptosis. Conclusion and Implications New quinolone derivatives were identified as potential pro-apoptotic agents. Compound 11e could be a promising lead compound for future antitumour agent development.

Design and synthesis of 5-alkoxy-[1,2,4]triazolo[4,3-a]quinoline derivatives with anticonvulsant activity

A series of 5-alkoxy-[1,2,4]triazolo[4,3-a]quinoline derivatives were synthesized using 4-hydroxyquinolin-2(1H)-one as the starting material. Their anticonvulsant activities were evaluated by the maximal electroshock test (MES) and their neurotoxicities w