946712-03-4

Basic information

• Product Name: 2-(chloromethyl)-1H-quinolin-4-one
• Synonyms: 2-(Chloromethyl)quinolin-4(1H)-one; 4(1H)-quinolinone, 2-(chloromethyl)-
• CAS NO: 946712-03-4
• Molecular Formula: C₁₀H₈ClNO
• Molecular Weight: 193.6296
• Mol File: 946712-03-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 306.7°C at 760 mmHg
• Flash Point: 139.3°C
• Density: 1.269g/cm³
• Vapor Pressure: 0.00076mmHg at 25°C
• Refractive Index: 1.584
• CAS DataBase Reference: 2-(chloromethyl)-1H-quinolin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(chloromethyl)-1H-quinolin-4-one(946712-03-4)
• EPA Substance Registry System: 2-(chloromethyl)-1H-quinolin-4-one(946712-03-4)

Safety Data

• Hazardous Substances Data: 946712-03-4(Hazardous Substances Data)

Usage

General Description

2-(Chloromethyl)-1H-quinolin-4-one is a chemical compound with the molecular formula C10H8ClNO. It is a derivative of quinolin-4-one, which is a bicyclic aromatic organic compound. The presence of a chloromethyl group in the molecule makes it useful for various chemical reactions and synthetic processes. It can be used as a building block in the synthesis of various pharmaceuticals, agrochemicals, and other organic compounds. The compound has potential applications in the field of medicinal chemistry and drug discovery due to its structural features and reactivity. It is important to handle this compound with caution due to its potential health hazards and reactivity with other chemicals.

Upstream product

• 638-07-3 ethyl (2-chloroaceto)acetate 
• 62-53-3 aniline 

Downstream Products

• 303224-88-6 4-chloro-2-(chloromethyl)quinoline 

Relevant articles and documents

Syntheses and characterization of non-bisphosphonate quinoline derivatives as new FPPS inhibitors

Background Farnesyl pyrophosphate synthase (FPPS) is a key regulatory enzyme in the biosynthesis of cholesterol and in the post-translational modification of signaling proteins. It has been reported that non-bisphosphonate FPPS inhibitors targeting its allosteric binding pocket are potentially important for the development of promising anti-cancer drugs. Methods The following methods were used: organic syntheses of non-bisphosphonate quinoline derivatives, enzyme inhibition studies, fluorescence titration assays, synergistic effect studies of quinoline derivatives with zoledronate, ITC studies for the binding of FPPS with quinoline derivatives, NMR-based HAP binding assays, molecular modeling studies, fluorescence imaging assay and MTT assays. Results We report our syntheses of a series of quinoline derivatives as new FPPS inhibitors possibly targeting the allosteric site of the enzyme. Compound 6b showed potent inhibition to FPPS without significant hydroxyapatite binding affinity. The compound showed synergistic inhibitory effect with active-site inhibitor zoledronate. ITC experiment confirmed the good binding effect of compound 6b to FPPS, and further indicated the binding ratio of 1:1. Molecular modeling studies showed that 6b could possibly bind to the allosteric binding pocket of the enzyme. The fluorescence microscopy indicated that these compounds could get into cancer cells. Conclusions Our results showed that quinoline derivative 6b could become a new lead compound for further optimization for cancer treatment. General significance The traditional FPPS active-site inhibitors bisphosphonates show poor membrane permeability to tumor cells, due to their strong polarity. The development of new non-bisphosphonate FPPS inhibitors with good cell membrane permeability is potentially important.