84772-27-0

Basic information

• Product Name: 6-CHLORO-3-PHENYL-2-THIOXO-2,3-DIHYDRO-4(1H)-QUINAZOLINONE
• Synonyms: 6-CHLORO-3-PHENYL-2-THIOXO-2,3-DIHYDRO-4(1H)-QUINAZOLINONE;6-Chloro-3-phenyl-2-thioxo-2,3-dihydro-1H-quinazolin-4-one;6-Chloro-2,3-dihydro-3-phenyl-2-thioxo-1H-quinazolin-4-one
• CAS NO: 84772-27-0
• Molecular Formula: C₁₄H₉ClN₂OS
• Molecular Weight: 288.75206
• Mol File: 84772-27-0.mol
• Article Data: 12

Chemical Properties

• Melting Point: >350
• Boiling Point: 455.1 °C at 760 mmHg
• Flash Point: 229.1 °C
• Appearance: /
• Density: 1.5 g/cm³
• Vapor Pressure: 1.8E-08mmHg at 25°C
• Refractive Index: 1.753
• PKA: 10.57±0.20(Predicted)
• CAS DataBase Reference: 6-CHLORO-3-PHENYL-2-THIOXO-2,3-DIHYDRO-4(1H)-QUINAZOLINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLORO-3-PHENYL-2-THIOXO-2,3-DIHYDRO-4(1H)-QUINAZOLINONE(84772-27-0)
• EPA Substance Registry System: 6-CHLORO-3-PHENYL-2-THIOXO-2,3-DIHYDRO-4(1H)-QUINAZOLINONE(84772-27-0)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 84772-27-0(Hazardous Substances Data)

Usage

General Description

6-Chloro-3-phenyl-2-thioxo-2,3-dihydro-4(1H)-quinazolinone is a chemical compound that belongs to the quinazolinone class of compounds. It contains a quinazolinone ring system with a chlorine atom at the 6-position, a phenyl group at the 3-position, and a thioxo group at the 2-position. 6-CHLORO-3-PHENYL-2-THIOXO-2,3-DIHYDRO-4(1H)-QUINAZOLINONE has been studied for its potential pharmacological properties, including its activity as an antitumor and anticancer agent. It has also been investigated for its potential as a scaffold for the development of novel pharmaceuticals. The precise biological and chemical activities of this compound are the subject of ongoing research in the field of medicinal chemistry.

InChI:InChI=1/C14H9ClN2OS/c15-9-6-7-12-11(8-9)13(18)17(14(19)16-12)10-4-2-1-3-5-10/h1-8H,(H,16,19)

Upstream product

• 103-72-0 phenyl isothiocyanate 
• 635-21-2 5-chloroanthranilic acid 
• 40763-96-0 2-nitro-5-chlorobenzamide 

Downstream Products

• 132968-23-1 7-Chloro-1-(6-chloro-4-oxo-3-phenyl-3,4-dihydro-quinazolin-2-ylsulfanylmethyl)-4-ethyl-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one 
• 13191-02-1 6-chloro-3-phenyl-2,4(1H,3H)-quinazolinedione 
• 31730-51-5 6-chloro-2-hydrazino-3-phenyl-3H-quinazolin-4-one 
• 174869-09-1 6-Chloro-3-phenyl-4(3H)-quinazolinone-2-ylmercaptoacetic acid ethyl ester 
• 174869-10-4 2-((6-chloro-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetohydrazide 
• 174869-12-6 C₁₉H₁₈ClN₅O₂S₂ 
• 174869-24-0 C₂₃H₁₇Cl₂N₅O₂S₂ 
• 174869-25-1 C₂₃H₁₇BrClN₅O₂S₂ 
• 1380091-16-6 6-chloro-2-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methylthio)-3-phenylquinazolin-4(3H)-one 
• 1380091-18-8 6-chloro-2-((1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)methylthio)-3-phenylquinazolin-4(3H)-one 
• 1380091-17-7 6-chloro-2-((1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl)methylthio)-3-phenylquinazolin-4(3H)-one 
• 1402932-22-2 C₂₁H₁₅ClN₂OS 
• 1402932-20-0 C₁₉H₁₇ClN₂OS 
• 1443205-03-5 C₁₇H₁₁ClN₄OS₂ 

Relevant articles and documents

Quinazolin-4(3H)-one based potential multiple tyrosine kinase inhibitors with excellent cytotoxicity

A series of quinazolin-4(3H)-one derivatives were synthesised and evaluated for their cytotoxicity against human Caucasian breast adenocarcinoma (MCF-7) and human ovarian carcinoma (A2780) cell lines. Cytotoxicity of the most tested compounds was 2- to 30-fold more than the positive control lapatinib (IC50 of 2j = 3.79 ± 0.96; 3j = 0.20 ± 0.02; and lapatinib = 5.9 ± 0.74) against MCF7 cell lines except two compounds (IC50 of 2 b = 15.72 ± 0.07 and 2e = 14.88 ± 0.99). On the other hand, cytotoxicity was 4 ? 87 folds (IC50 of 3a = 3.00 ± 1.20; 3 g = 0.14 ± 0.03) more the positive control lapatinib (IC50 = 12.11 ± 1.03) against A2780 cell lines except compound 2e (IC50 = 16.43 ± 1.80). Among the synthesised quinazolin-4(3H)-one derivatives, potent cytotoxic 2f-j and 3f-j were investigated for molecular mechanism of action. Inhibitory activities of the compounds were tested against multiple tyrosine protein kinases (CDK2, HER2, EGFR and VEGFR2) enzymes. As expected, all the quinazolin-4(3H)-one derivatives were showed comparable inhibitory activity against those kinases tested, especially, compound 2i and 3i showed potent inhibitory activity against CDK2, HER2, EGFR tyrosine kinases. Therefore, molecular docking analysis for quinazolin-4(3H)-one derivatives 2i and 3i were performed, and it was revealed that compounds 2i and 3i act as ATP non-competitive type-II inhibitor against CDK2 kinase enzymes and ATP competitive type-I inhibitor against EGFR kinase enzymes. However, in case of HER2, compounds 2i act as ATP non-competitive type-II inhibitor and 3i act as ATP competitive type-I inhibitor. Docking results of known inhibitors were compared with synthesised compounds and found synthesised 2i and 3i are superior than the known inhibitors in case of interactions. In addition, in silico drug likeness properties of quinazolin-4(3H)-one derivatives showed better predicted ADME values than lapatinib.

Design, Synthesis, Anticancer Activity, and Cell Cycle Analysis of Novel Quinazoline Derivatives Targeting VEGFR-2 Kinase

Abstract: Novel quinazoline derivatives have been designed, synthesized and tested for cytotoxic activity against HCT116, and MCF-7 cell lines. The preliminary data indicate their promising antitumor potential. Enzyme inhibitory activity of the most active product against VEGFR-2 has been assessed. Apoptosis and cell cycle arrest during the G2/M phase has been triggered by the product, and according to the gene expression data, it increases BAX and caspase-3 expression while decreasing Bcl-2 expression.

Discovery of Potent and Novel Quinazolinone Sulfide Inhibitors with Anti-ToCV Activity

A series of novel quinazolinone sulfide derivatives containing a dithioacetal moiety were designed and synthesized using Tomato chlorosis virus coat protein (ToCVCP) as a potential drug target, and the inhibitory effect of ToCV was systematically evaluate