3817-05-8

Basic information

• Product Name: 2-(CHLOROMETHYL)-4(3H)-QUINAZOLINONE
• Synonyms: 2-Chloromethyl-4-(3H)-quinozolinone;2-(Chloromethyl)quinazlin-4-ol;2-ChloroMethyl-3H-quinazolin-4-one;2-(chloroMethyl)-3,4-dihydroquinazolin-4-one;2-(Chloromethyl)-4(1H)-quinazolinone;2-ChloroMethyl-1H-quinazolin-4-one;2-(Chloromethyl)-4(3H)-quinazolinone 97%
• CAS NO: 3817-05-8
• Molecular Formula: C₉H₇ClN₂O
• Molecular Weight: 194.62
• Product Categories: Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Quinazolines;QuinazolinesHeterocyclic Building Blocks
• Mol File: 3817-05-8.mol
• Article Data: 34

Chemical Properties

• Melting Point: 249-253 °C(lit.)
• Boiling Point: 340.7°Cat760mmHg
• Flash Point: 159.9°C
• Appearance: /
• Density: 1.42
• Vapor Pressure: 8.43E-05mmHg at 25°C
• Refractive Index: 1.662
• PKA: 1.26±0.20(Predicted)
• CAS DataBase Reference: 2-(CHLOROMETHYL)-4(3H)-QUINAZOLINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(CHLOROMETHYL)-4(3H)-QUINAZOLINONE(3817-05-8)
• EPA Substance Registry System: 2-(CHLOROMETHYL)-4(3H)-QUINAZOLINONE(3817-05-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36-43
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 3817-05-8(Hazardous Substances Data)

Usage

General Description

2-(Chloromethyl)-4(3H)-quinazolinone, also known as CMQ, is a chemical compound that belongs to the quinazolinone family. It is a potent and selective antagonist of the human A3 adenosine receptor, which plays a role in regulating inflammation and immune responses. CMQ has been studied for its potential anti-inflammatory and anti-cancer properties, as well as its ability to modulate the immune system. It has also been investigated as a potential therapeutic agent for the treatment of conditions such as asthma, arthritis, and certain types of cancer. Additionally, CMQ has shown promise as a tool for studying the role of the A3 adenosine receptor in various physiological and pathological processes.

InChI:InChI=1/C9H7ClN2O/c10-5-8-11-7-4-2-1-3-6(7)9(13)12-8/h1-4H,5H2,(H,11,12,13)

Upstream product

• 21721-78-8 2-ω-chloroacetylaminobenzamide 
• 58915-18-7 methyl N-(chloroacetyl)anthranilate 
• 107-14-2 chloroacetonitrile 
• 134-20-3 2-carbomethoxyaniline 
• 1769-24-0 2-methyl-4-quinazolone 
• 71993-21-0 [(2-cyanophenyl)aminocarbonylmethyl]chloride 
• 28144-70-9 anthranilic acid amide 
• 79-11-8 chloroacetic acid 
• 87-25-2 2-ethoxycarbonylaniline 
• 1885-29-6 anthranilic acid nitrile 
• 79-04-9 chloroacetyl chloride 
• 118-92-3 anthranilic acid 
• 32807-28-6 Methyl 4-chloroacetoacetate 
• 638-07-3 ethyl (2-chloroaceto)acetate 

Downstream Products

• 134577-50-7 2-(p-Tolylamino-methyl)-3H-quinazolin-4-one 
• 134577-54-1 2-[(4-Chloro-phenylamino)-methyl]-3H-quinazolin-4-one 
• 134577-52-9 2-{[(4-methoxyphenyl)amino]methyl}quinazolin-4(3H)-one 
• 3817-06-9 2-Phenylaminomethyl-3H-quinazolin-4-one 
• 134577-53-0 2-[(4-Ethoxy-phenylamino)-methyl]-3H-quinazolin-4-one 
• 134577-51-8 2-[(4-Ethyl-phenylamino)-methyl]-3H-quinazolin-4-one 
• 143707-89-5 2-[(5-Ethyl-6-methyl-2-oxo-1,2-dihydro-pyridin-3-ylamino)-methyl]-3H-quinazolin-4-one 
• 194496-83-8 2-(4-Chloro-phenyl)-10,10a-dihydro-3aH-2,3b,9-triaza-pentaleno[1,2-b]naphthalene-1,3,4-trione 
• 194496-92-9 1-(4-Chloro-phenyl)-2-nitro-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one 
• 34637-41-7 4-chloro-2-(chloromethyl)quinazoline 

Relevant articles and documents

In Vivo and Mechanistic Studies on Antitumor Lead 7-Methoxy-4-(2-methylquinazolin-4-yl)-3,4-dihydroquinoxalin-2(1H)-one and Its Modification as a Novel Class of Tubulin-Binding Tumor-Vascular Disrupting Agents

7-Methoxy-4-(2-methylquinazolin-4-yl)-3,4-dihydroquinoxalin-2(1H)-one (2), a promising anticancer lead previously identified by us, inhibited tumor growth by 62% in mice at 1.0 mg/kg without obvious signs of toxicity. Moreover, compound 2 exhibited extremely high antiproliferative activity in the NIH-NCI 60 human tumor cell line panel, with low to sub-nanomolar GI50 values (10-10 M level). It also showed a suitable balance between aqueous solubility and lipophilicity, as well as moderate metabolic stability in vivo. Mechanistic studies using Mayer's hematoxylin and eosin and immunohistochemistry protocols on xenograft tumor tissues showed that 2 inhibited tumor cell proliferation, induced apoptosis, and disrupted tumor vasculature. Moreover, evaluation of new synthetic analogues (6a-6t) of 2 indicated that appropriate 2-substitution on the quinazoline ring could enhance antitumor activity and improve druglike properties. Compound 2 and its analogues with a 4-(2-methylquinazolin-4-yl)-3,4-dihydroquinoxalin-2(1H)-one scaffold thus represent a novel class of tubulin-binding tumor-vascular disrupting agents (tumor-VDAs) that target established blood vessels in tumors.

Design and synthesis of new benzopyrimidinone derivatives: α-amylase inhibitory activity, molecular docking and DFT studies

New benzopyrimidinone derivatives have been synthesized by reaction of 2-aminobenzamide with different acyl chlorides in good yield and their structures were confirmed by 1H NMR, 13C NMR and mass spectrometry. The newly synthesized c

Tankyrase inhibitor

The invention belongs to the technical field of medicines and particularly relates to a tankyrase inhibitor represented by a general formula (I) shown in the description and pharmaceutically acceptable salts, esters, solvates or stereoisomers thereof, wherein R1, R2, R3, m, n, Z, L, Q, A, X1, X2 and Y are as defined in the description. The invention further relates to a preparation method for the compounds, pharmaceutical preparations and pharmaceutical compositions containing the compounds and application of the compound and the pharmaceutically acceptable salts, esters, solvates or stereoisomers thereof in preparation of drugs for treating and/or preventing tankyrase mediated cancers and related diseases.