96682-70-1

Basic information

• Product Name: 3H-Indol-3-one, 1-acetyl-2-[(4-bromophenyl)methylene]-1,2-dihydro-
• CAS NO: 96682-70-1
• Molecular Formula: C17H12BrNO2
• Molecular Weight: 342.192
• Mol File: 96682-70-1.mol

Chemical Properties

• CAS DataBase Reference: 3H-Indol-3-one, 1-acetyl-2-[(4-bromophenyl)methylene]-1,2-dihydro-(CAS DataBase Reference)
• NIST Chemistry Reference: 3H-Indol-3-one, 1-acetyl-2-[(4-bromophenyl)methylene]-1,2-dihydro-(96682-70-1)
• EPA Substance Registry System: 3H-Indol-3-one, 1-acetyl-2-[(4-bromophenyl)methylene]-1,2-dihydro-(96682-70-1)

Safety Data

• Hazardous Substances Data: 96682-70-1(Hazardous Substances Data)

Upstream product

• 16800-68-3 1-acetyl-2,3-dihydro-1H-indol-3-one 
• 1122-91-4 4-bromo-benzaldehyde 
• 68095-22-7 N-(2-(2-chloroacetyl)phenyl)acetamide 
• 62-53-3 aniline 
• 64605-23-8 2'-amino-2-chloroacetophenone 

Downstream Products

• 97583-95-4 4-(4-Bromo-phenyl)-2-methoxy-5H-pyrido[3,2-b]indole-3-carbonitrile 
• 144294-95-1 2-(4-bromophenyl)-3-methoxyquinolin-4(1H)-one 
• 144294-89-3 4'-bromo-1H-2-phenyl-3-hydroxy-4-oxoquinoline 
• 120642-62-8 (2-Amino-phenyl)-[5-(4-bromo-phenyl)-1H-[1,2,3]triazol-4-yl]-methanone 
• 97583-88-5 5-Acetyl-2-amino-4-(4-bromo-phenyl)-4,5-dihydro-pyrano[3,2-b]indole-3-carbonitrile 
• 144294-84-8 1-Acetyl-2-bromo-2-[bromo-(4-bromo-phenyl)-methyl]-1,2-dihydro-indol-3-one 
• 144294-78-0 1-Acetyl-2-[(4-bromo-phenyl)-chloro-methyl]-2-chloro-1,2-dihydro-indol-3-one 
• 120642-60-6 N-{2-[5-(4-Bromo-phenyl)-1H-[1,2,3]triazole-4-carbonyl]-phenyl}-acetamide 
• 96682-75-6 2-Amino-3-(4-bromo-phenyl)-1H-quinolin-4-one 
• 96682-80-3 2-[1-Amino-1-(4-bromo-phenyl)-meth-(Z)-ylidene]-1,2-dihydro-indol-3-one 

Relevant articles and documents

Probing the Azaaurone Scaffold against the Hepatic and Erythrocytic Stages of Malaria Parasites

The potential of azaaurones as dual-stage antimalarial agents was investigated by assessing the effect of a small library of azaaurones on the inhibition of liver and intraerythrocytic lifecycle stages of the malaria parasite. The whole series was screened against the blood stage of a chloroquine-resistant Plasmodium falciparum strain and the liver stage of P. berghei, yielding compounds with dual-stage activity and sub-micromolar potency against erythrocytic parasites. Studies with genetically modified parasites, using a phenotypic assay based on the P. falciparum Dd2-ScDHODH line, which expresses yeast dihydroorotate dehydrogenase (DHODH), showed that one of the azaaurone derivatives has the potential to inhibit the parasite mitochondrial electron-transport chain. The global urgency in finding new therapies for malaria, especially against the underexplored liver stage, associated with chemical tractability of azaaurones, warrants further development of this chemotype. Overall, these results emphasize the azaaurone chemotype as a promising scaffold for dual-stage antimalarials.

Azaaurones as Potent Antimycobacterial Agents Active against MDR- and XDR-TB

Herein we report the screening of a small library of aurones and their isosteric counterparts, azaaurones and N-acetylazaaurones, against Mycobacterium tuberculosis. Aurones were found to be inactive at 20 μm, whereas azaaurones and N-acetylazaaurones emerged as the most potent compounds, with nine derivatives displaying MIC99 values ranging from 0.4 to 2.0 μm. In addition, several N-acetylazaaurones were found to be active against multidrug-resistant (MDR) and extensively drug-resistant (XDR) clinical M. tuberculosis isolates. The antimycobacterial mechanism of action of these compounds remains to be determined; however, a preliminary mechanistic study confirmed that they do not inhibit the mycobacterial cytochrome bc1 complex. Additionally, microsomal metabolic stability and metabolite identification studies revealed that N-acetylazaaurones are deacetylated to their azaaurone counterparts. Overall, these results demonstrate that azaaurones and their N-acetyl counterparts represent a new entry in the toolbox of chemotypes capable of inhibiting M. tuberculosis growth.

NEW METHOD OF SYNTHESIS OF δ-CARBOLINES FROM 3-INDOLINONE VIA PYRANOINDOLES

2-Arylidene-1-acetylindolin-3-ones were obtained from 1-acetylindolin-3-ones and p-substituted benzaldehydes or 4-pyridinecarboxaldehyde, by the action of malonodinitrile, and were converted into 2-amino-4-aryl-5-acetyl-3-cyanopyranoindoles.When heated with an aqueous-alcoholic solution of KOH, the latter compounds transform into 2-alkoxy-4-aryl-3-cyano-δ-carbolines.The possible paths of formation of δ-carbolines and pyranoindoles are discussed.