552330-87-7

Basic information

• Product Name: 6-bromocinnolin-4(1H)-one
• Synonyms: 6-bromocinnolin-4(1H)-one;6-broMo-1,4-dihydrocinnolin-4-one;6-BroMo-1H-cinnolin-4-one;6-Bromo-4(1H)-cinnolinone
• CAS NO: 552330-87-7
• Molecular Formula: C₈H₅BrN₂O
• Molecular Weight: 225.0421
• Mol File: 552330-87-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 374.174 °C at 760 mmHg
• Flash Point: 180.095 °C
• Appearance: /
• Density: 1.82
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.721
• PKA: -3.23±0.20(Predicted)
• CAS DataBase Reference: 6-bromocinnolin-4(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-bromocinnolin-4(1H)-one(552330-87-7)
• EPA Substance Registry System: 6-bromocinnolin-4(1H)-one(552330-87-7)

Safety Data

• Hazardous Substances Data: 552330-87-7(Hazardous Substances Data)

Usage

General Description

6-bromocinnolin-4(1H)-one is a chemical compound with the molecular formula C9H5BrN2O. It is a cinnoline derivative, which are heterocyclic aromatic compounds containing a cinnoline ring system. 6-bromocinnolin-4(1H)-one has a bromine atom attached to the cinnoline ring and a carbonyl group at the 4-position. 6-bromocinnolin-4(1H)-one is used in organic synthesis and as a building block for the construction of more complex chemical compounds. It also has potential pharmaceutical applications and may be used in the development of drugs. Due to its structure and properties, it is important for the field of medicinal chemistry and drug discovery.

InChI:InChI=1/C8H5BrN2O/c9-5-1-2-7-6(3-5)8(12)4-10-11-7/h1-4H,(H,11,12)

Upstream product

• 29124-64-9 N-(2-acetyl-4-bromophenyl)acetamide 
• 13631-76-0 (4-bromo-phenylhydrazono)-malonic acid diethyl ester 
• 624-19-1 4-bromoaniline hydrochloride 
• 20357-04-4 (5-bromo-2-nitro-phenyl)-propiolic acid 
• 90271-82-2 (4-bromo-phenylhydrazono)-malonyl chloride 
• 90484-39-2 (4-bromo-phenylhydrazono)-malonic acid 
• 5234-26-4 N-(2-acetylphenyl)acetamide 
• 551-93-9 2-aminoacetophenone 
• 29124-56-9 1-(2-amino-5-bromophenyl)ethanone 
• 61588-11-2 6-bromo-4-oxo-1,4-dihydro-3-cinnolinecarboxylic acid 

Downstream Products

• 68211-13-2 4,6-dichlorocinnoline 
• 68211-15-4 6-bromo-4-chlorocinnoline 
• 872284-86-1 6-bromo-3-chloro-1H-cinnolin-4-one 
• 318276-72-1 6-bromocinnoline 

Relevant articles and documents

Discovery of Pyridopyrimidinones as Potent and Orally Active Dual Inhibitors of PI3K/mTOR

The identification and lead optimization of a series of pyridopyrimidinone derivatives are described as a novel class of efficacious dual PI3K/mTOR inhibitors, resulting in the discovery of 31. Compound 31 exhibited high enzyme activity against PI3K and mTOR, potent suppression of Akt and p70s6k phosphorylation in cell assays, and good pharmacokinetic profile. Furthermore, compound 31 demonstrated in vivo efficacy in a PC-3M tumor xenograft model.

Protozoan Parasite Growth Inhibitors Discovered by Cross-Screening Yield Potent Scaffolds for Lead Discovery

Tropical protozoal infections are a significant cause of morbidity and mortality worldwide; four in particular (human African trypanosomiasis (HAT), Chagas disease, cutaneous leishmaniasis, and malaria) have an estimated combined burden of over 87 million disability-adjusted life years. New drugs are needed for each of these diseases. Building on the previous identification of NEU-617 (1) as a potent and nontoxic inhibitor of proliferation for the HAT pathogen (Trypanosoma brucei), we have now tested this class of analogs against other protozoal species: T. cruzi (Chagas disease), Leishmania major (cutaneous leishmaniasis), and Plasmodium falciparum (malaria). Based on hits identified in this screening campaign, we describe the preparation of several replacements for the quinazoline scaffold and report these inhibitors' biological activities against these parasites. In doing this, we have identified several potent proliferation inhibitors for each pathogen, such as 4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-6-(4-((4-methyl-1,4-diazepan-1-yl)sulfonyl)phenyl)quinoline-3-carbonitrile (NEU-924, 83) for T. cruzi and N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-7-(4-((4-methyl-1,4-diazepan-1-yl)sulfonyl)phenyl)cinnolin-4-amine (NEU-1017, 68) for L. major and P. falciparum.

Synthesis and SAR of indazole-pyridine based protein kinase B/Akt inhibitors

A series of heteroaryl-pyridine containing inhibitors of Akt are reported. The synthesis and structure-activity relationships are discussed, leading to the discovery of a indazole-pyridine analogue (Ki = 0.16 nM). These compounds bind in the ATP binding site, are potent, ATP competitive, and reversible inhibitors of Akt activity. No selectivity amongst the Akt isoforms is observed for this analogue, but there is good selectivity against an panel of other kinases. It is least selective for other members of the AGC family of kinases but is nonetheless 40-fold selective for Akt over PKA. The compound shows cellular activity and significantly slows tumor growth in vivo.