20780-74-9

Basic information

• Product Name: 7-BROMO-1H-INDOLE-2,3-DIONE
• Synonyms: BUTTPARK 50\07-96;7-BROMOINDOLINE-2,3-DIONE;7-BROMO-ISATIN;7-BROMO-2,3-DIOXOINDOLINE;7-BROMO-1H-INDOLE-2,3-DIONE;7-Bromoisatin 97%;7-BROMOINDOLE-3-CARBOXALDEHYDE;7-Bromoindoline-2,3-dione, 7-Bromo-1H-indole-2,3-dione
• CAS NO: 20780-74-9
• Molecular Formula: C₈H₄BrNO₂
• Molecular Weight: 226.03
• EINECS: 1308068-626-2
• Product Categories: Heterocycles;Indane/Indanone and Derivatives;Pharmaceutical intermediate
• Mol File: 20780-74-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 199 °C
• Appearance: /
• Density: 1.826 g/cm³
• Refractive Index: 1.649
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Slightly soluble.
• PKA: 8.69±0.20(Predicted)
• CAS DataBase Reference: 7-BROMO-1H-INDOLE-2,3-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-BROMO-1H-INDOLE-2,3-DIONE(20780-74-9)
• EPA Substance Registry System: 7-BROMO-1H-INDOLE-2,3-DIONE(20780-74-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39
• WGK Germany: 3
• Hazardous Substances Data: 20780-74-9(Hazardous Substances Data)

Usage

Uses

7-bromoisatin was treated with excess PhMgBr to afford tertiary alcohol 9 in 96 % yield. Isatin oxime triflates undergo a facile fragmentation which is promoted by DBU, to form anthranilonitriles after hydrolytic work-up.

InChI:InChI=1/C8H4BrNO2/c9-5-3-1-2-4-6(5)10-8(12)7(4)11/h1-3H,(H,10,11,12)

Upstream product

• 101080-38-0 N-(2-bromophenyl)-2-isonitrosoacetanilide 

Downstream Products

• 1368204-76-5 2-amino-3-bromo-N-ethylbenzamide 
• 1410975-92-6 (7aS,9S)-6-(3-methyl-4-oxo-3,4-dihydroquinazolin-8-yl)-2-methylthio-9-(4-nitrobenzoyloxy)-6,7,7a,8,9,10-hexahydro-5H-pyrimido[5,4-f]pyrrolo[1,2-a][1,4]diazepin-5-one 
• 1022960-45-7 2-amino-3-bromo-N-methylbenzamide 
• 1410974-28-5 3-bromo-2-(2-methoxyacetamido)-N-methylbenzamide 
• 1410974-23-0 2-amino-3-bromo-N-(2-hydroxyethyl)benzamide 
• 1367962-46-6 2-amino-3-bromo-N-(2-methoxyethyl)benzamide 
• 1448778-70-8 6-bromo-2-(4-methoxyphenyl)-4-methyl-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione 
• 63220-44-0 7-bromo-3-hydroxy-3-phenyl-1,3-dihydroindol-2-one 
• 1434103-28-2 8-(4-fluorophenyl)-3-methoxyquinolin-2(1H)-one 
• 1434103-16-8 8-(4-fluorophenyl)-3-hydroxyquinolin-2(1H)-one 
• 121490-67-3 8-bromoquinoline-4-carboxylic acid 

Relevant articles and documents

Indirubin core structure of glycogen synthase kinase-3 inhibitors as novel chemotype for intervention with 5-lipoxygenase

The enzymes 5-lipoxygenase (5-LO) and glycogen synthase kinase (GSK)-3 represent promising drug targets in inflammation. We made use of the bisindole core of indirubin, present in GSK-3 inhibitors, to innovatively target 5-LO at the ATP-binding site for the design of dual 5-LO/GSK-3 inhibitors. Evaluation of substituted indirubin derivatives led to the identification of (3Z)-6-bromo-3-[(3E)-3-hydroxyiminoindolin-2-ylidene]indolin-2-one (15) as a potent, direct, and reversible 5-LO inhibitor (IC50 = 1.5 μM), with comparable cellular effectiveness on 5-LO and GSK-3. Together, we present indirubins as novel chemotypes for the development of 5-LO inhibitors, the interference with the ATP-binding site as a novel strategy for 5-LO targeting, and dual 5-LO/GSK-3 inhibition as an unconventional and promising concept for anti-inflammatory intervention.