18009-07-9

Usage

InChI:InChI=1/C14H9BrN2OS/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

• 5794-88-7 5-Bromo-2-aminobenzoic acid 
• 4955-82-2 1-cyanothioformanilide 
• 103-72-0 phenyl isothiocyanate 

Downstream Products

• 174020-06-5 Acetic acid (2S,3R,4S,5S)-4,5-diacetoxy-2-(6-bromo-4-oxo-3-phenyl-3,4-dihydro-quinazolin-2-ylsulfanyl)-tetrahydro-pyran-3-yl ester 
• 174020-06-5 Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-(6-bromo-4-oxo-3-phenyl-3,4-dihydro-quinazolin-2-ylsulfanyl)-tetrahydro-pyran-3-yl ester 
• 1383992-14-0 C₂₂H₁₈BrN₃O₂ 
• 1383991-65-8 C₁₄H₈BrClN₂O 
• 1383992-15-1 2-amino-6-bromo-3-phenylquinazolin-4(3H)-one 
• 1449795-03-2 N-(5-(2-amino-4-oxo-3-phenyl-3,4-dihydroquinazolin-6-yl)-2-methoxyphenyl)-2,4-difluorobenzenesulfonamide 
• 1402932-19-7 C₁₉H₁₇BrN₂OS 
• 701245-01-4 C₂₁H₁₅BrN₂OS 
• 18009-19-3 6-bromo-2-methylsulfanyl-3-phenyl-3H-quinazolin-4-one 
• 116862-09-0 C₂₈H₁₆Br₂N₄O₂S 
• 84772-19-0 6-bromo-2-hydrazino-3-phenyl-3H-quinazolin-4-one 
• 23965-11-9 6-bromo-3-phenylquinazoline-2,4(1H,3H)-dione 
• 80416-46-2 1-[2-(6-Bromo-4-oxo-3-phenyl-3,4-dihydro-quinazolin-2-ylsulfanyl)-acetyl]-3-m-tolyl-urea 
• 80416-45-1 1-[2-(6-Bromo-4-oxo-3-phenyl-3,4-dihydro-quinazolin-2-ylsulfanyl)-acetyl]-3-o-tolyl-urea 

Relevant academic research and scientific papers

Application of Deep Eutectic Solvents in the Synthesis of Substituted 2-Mercaptoquinazolin-4(3H)-Ones: A Comparison of Setected Green Chemistry Methods

In this study, deep eutectic solvents (DESs) were used as green and eco-friendly media for the synthesis of substituted 2-mercaptoquinazolin-4(3H)-ones from different anthranilic acids and aliphatic or aromatic isothiocyanates. A model reaction on anthranilic acid and phenyl isothiocyanate was porformed in 20 choline chloride-based DESs at 80 °C to find the best solvent. Based on the product yield, choline chloride-urea (1:2) DES was found to be the most effective, while DESs acted both as solvents and catalysts. Desired compounds were prepared with moderate to good yields using stirring, microwave-assisted, and ultrasound-assisted synthesis. Significantly, higher yields were obtained with mixing and ultrasonication (16-76%), while microwave-induced synthesis showed lower effectiveness (13-49%). The specific contribution of this research is the use of DESs in combination with the above-mentioned green techniques for the synthesis of a wide range of derivatives. The structures of the synthesized compounds were confirmed by1H and13C NMR spectroscopy.

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 selective small molecule type III phosphatidylinositol 4-kinase alpha (PI4KIIIα) inhibitors as anti hepatitis C (HCV) agents

Hepatitis C virus (HCV) assembles many host cellular proteins into unique membranous replication structures as a prerequisite for viral replication, and PI4KIIIα is an essential component of these replication organelles. RNA interference of PI4KIIIα results in a breakdown of this replication complex and cessation of HCV replication in Huh-7 cells. PI4KIIIα is a lipid kinase that interacts with the HCV nonstructural 5A protein (NS5A) and enriches the HCV replication complex with its product, phosphoinositol 4-phosphate (PI4P). Elevated levels of PI4P at the endoplasmic reticulum have been linked to HCV infection in the liver of HCV infected patients.1 We investigated if small molecule inhibitors of PI4KIIIα could inhibit HCV replication in vitro. The synthesis and structure-activity relationships associated with the biological inhibition of PI4KIIIα and HCV replication are described. These efforts led directly to identification of quinazolinone 28 that displays high selectivity for PI4KIIIα and potently inhibits HCV replication in vitro.

Design, synthesis and biological activity evaluation of 2-mercapto-4(3H)-quinazolinone derivatives as novel inhibitors of protein tyrosine phosphatase 1B

A series of novel 2-mercapto-4(3H)-quinazolinone derivatives have been synthesized and their inhibitory effects on PTP1B and TCPTP are evaluated for the first time. Most of these derivatives showed good inhibitory activity on PTP1B and reasonable selectivity for PTP1B over TCPTP, among them 32 was the most potent PTP1B inhibitor (IC50 = 1.50 μ ;g/mL), and 27 possessed the best selectivity of 3.0-fold.

COMPOUND THAT IS A DUAL INHIBITOR OF ENZYMES PDE7 AND/OR PDE4, PHARMACEUTICAL COMPOSITIONS AND USES THEREOF

The invention relates to a series of dual inhibitors of enzymes PDE7 and PDE4, having formula (I) and to the use thereof in the production of pharmaceutical compositions for the treatment of inflammatory and/or autoimmune processes.

A comparative study of the behavior of cyanothioformamide and oxazolidine (thiones or iminothiones) towards some binucleophiles

Reactions of cyanothioformamides (I) with o-phenylenediamines, o-aminophenol, and anthranilic acids furnished benzimidazole (II,III), benzoxazole (VII), quinazoline (IX) derivatives, respectively. Oxazolidine (thiones or iminothiones) (IV) were reacted with the same binucleophiles to produce quinoxaline (V), benzimidazole (VI), and quinazoline (XI) derivatives.

Monoamine Oxidase and Succinate Dehydrogenase Inhibitory Properties of Substituted Mercaptoquinazolones

Twelve 6-substituted-2-(1'-mercaptoacetyl-3'-arylurea)-3-phenyl-4-quinazolones were synthesized by condensation of 6-substituted anthranilic acids and aryl isothiocyanates followed by reaction with chloroacetyl arylurea.These compounds were characterized by their sharp melting points and elemental analyses.All compounds were evaluated for their enzyme inhibitory activity.It was found that all substituted quinazolones at a final concentration of 2 x 10-4 M inhibited in vitro monoamine oxidase and succinate dehydrogenase activity of rat brain homogenates and the degree of inhibition ranged from 11-77percent and 25-53percent, respectively.