144189-81-1

Basic information

• Product Name: 2-(1-BROMO-ETHYL)-3H-QUINAZOLIN-4-ONE
• Synonyms: 2-(1-BROMO-ETHYL)-3H-QUINAZOLIN-4-ONE;2-(1-bromoethyl)-3,4-dihydroquinazolin-4-one
• CAS NO: 144189-81-1
• Molecular Formula: C₁₀H₉BrN₂O
• Molecular Weight: 253.09526
• Mol File: 144189-81-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 355.4±44.0 °C(Predicted)
• Appearance: /
• Density: 1.63±0.1 g/cm3(Predicted)
• PKA: 1.08±0.20(Predicted)
• CAS DataBase Reference: 2-(1-BROMO-ETHYL)-3H-QUINAZOLIN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1-BROMO-ETHYL)-3H-QUINAZOLIN-4-ONE(144189-81-1)
• EPA Substance Registry System: 2-(1-BROMO-ETHYL)-3H-QUINAZOLIN-4-ONE(144189-81-1)

Safety Data

• Hazardous Substances Data: 144189-81-1(Hazardous Substances Data)

Usage

Structure

Quinazolinone derivative with a bromoethyl group attached to the nitrogen atom in the quinazolinone ring

Potential applications

Medicinal chemistry, drug discovery, synthesis of biologically active molecules

Pharmacological properties

Potential as a drug candidate for various therapeutic purposes

Synthesis and characterization

Of interest to researchers in organic and pharmaceutical chemistry

Upstream product

• 28144-70-9 anthranilic acid amide 
• 129768-46-3 2-(α-Bromopropionyl)aminobenzamide 
• 3137-64-2 2-ethyl-3H-quinazolin-4-one 

Downstream Products

• 143993-29-7 2-(1-p-Tolylamino-ethyl)-3H-quinazolin-4-one 
• 143993-26-4 2-[1-(4-Chloro-phenylamino)-ethyl]-3H-quinazolin-4-one 
• 143993-20-8 2-(1-Benzylamino-ethyl)-3H-quinazolin-4-one 
• 143993-27-5 2-[1-(4-Fluoro-phenylamino)-ethyl]-3H-quinazolin-4-one 
• 815590-48-8 2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3H-quinazolin-4-one 
• 172420-51-8 3-Chloro-N-(4-methoxy-phenyl)-N-[1-(4-oxo-3,4-dihydro-quinazolin-2-yl)-ethyl]-propionamide 
• 216596-29-1 2-Bromo-N-(4-ethoxy-phenyl)-N-[1-(4-oxo-3,4-dihydro-quinazolin-2-yl)-ethyl]-propionamide 
• 216596-18-8 2-Chloro-N-(4-ethoxy-phenyl)-N-[1-(4-oxo-3,4-dihydro-quinazolin-2-yl)-ethyl]-acetamide 
• 216596-27-9 2-Bromo-N-(4-methoxy-phenyl)-N-[1-(4-oxo-3,4-dihydro-quinazolin-2-yl)-ethyl]-propionamide 
• 216596-28-0 2-Bromo-N-(4-fluoro-phenyl)-N-[1-(4-oxo-3,4-dihydro-quinazolin-2-yl)-ethyl]-propionamide 

Relevant articles and documents

Discovery of natural alkaloid bouchardatine as a novel inhibitor of adipogenesis/lipogenesis in 3T3-L1 adipocytes

Bouchardatine (1), a naturally occurring β-indoloquinazoline alkaloid, was synthesized. For the first time, the lipid-lowering effect and mechanism of 1 was investigated in 3T3-L1 adipocytes. Our study showed that 1 could significantly reduce lipid accumulation without cytotoxicity and mainly inhibited early differentiation of adipocyte through proliferation inhibition and cell cycle arrested in dose-dependent manner. Furthermore, the inhibition of early differentiation was reflected by down-regulation of key regulators of adipogenesis/lipogenesis, including CCAAT enhancer binding proteins (C/EBPβ, C/EBPδ, C/EBPα), peroxisome proliferator-activated receptors γ (PPARγ) and sterol-regulatory element binding protein-1c (SREBP-1c), in both of mRNA and protein levels. Subsequently decreasing the protein levels of acetyl CoA carboxylase (ACC), fatty acid synthase (FAS), and stearyl coenzyme A desaturated enzyme 1 (SCD-1), the rate-limited metabolic enzymes of fatty acid synthesis, were also observed. Further studies revealed that 1 persistently activated adenosine 5′-monophosphate (AMP)-activated protein kinase (AMPK) during differentiation, suggesting that the AMPK may be an upstream mechanism for the effect of 1 on adipogenesis and lipogenesis. Our data suggest that 1 can be a candidate for the development of new therapeutic drugs against obesity and related metabolic disorders.

PYRIMIDINE DERIVATIVES AS MODULATORS OF ATP-BINDING CASSETTE TRANSPORTERS

The present invention relates to compounds of Formula (I) as modulators of ATP-Binding Cassette (“ABC”) transporters or fragments thereof, including Cystic Fibrosis Transmembrane Regulator (“CFTR”), compositions thereof, and methods therewith. The present invention also relates to methods of treating ABC transporter mediated diseases using such modulators.

Synthesis of chrysogine, a metabolite of Penicillium chrysogenum and some related 2-substituted 4-(3H)-quinazolinones

Syntheses of both enantiomers of chrysogine, 2-(α-hydroxyethyl)-4(3H)-quinazolinone, 1 from 2-ammobenzamide are reported. Thus reaction of 2-aminobenzamide and optically active α-acetoxypropionyl chloride gave 9, which upon saponification and cyclization induced by aqueous sodium carbonate at room temperature gave chrysogine. The enantiomeric purity of 1 was determined by NMR. Inversion of (-)-(S)-1, using the Mitsunobo reaction, gave (+)-(R)-1. Reduction of 2-acetyl-4(3H)-qumazolinone 2 with baker's yeast gave the S-enantiomer of 1. The cyclization method used could be extended and a number of 2-(a-hydroxy)alkyl-4-(3H)-quinazolinones are also reported.