20780-74-9 Usage
Description
7-BROMO-1H-INDOLE-2,3-DIONE is an organic compound with the molecular formula C8HBrNO2. It is a derivative of isatin, featuring a bromo substituent at the 7th position and a dione group at the 2nd and 3rd positions. 7-BROMO-1H-INDOLE-2,3-DIONE is known for its potential applications in various fields due to its unique chemical structure and reactivity.
Uses
Used in Pharmaceutical Industry:
7-BROMO-1H-INDOLE-2,3-DIONE is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for further chemical modifications, making it a valuable building block for the development of new drugs.
Used in Chemical Research:
In the field of chemical research, 7-BROMO-1H-INDOLE-2,3-DIONE serves as a key compound for studying the reactivity and properties of indole-based molecules. It can be used to explore new reaction pathways and develop innovative synthetic methods.
Used in Synthesis of Tertiary Alcohols:
7-BROMO-1H-INDOLE-2,3-DIONE is used as a starting material for the synthesis of tertiary alcohols, such as compound 9, which was obtained with a 96% yield when treated with excess PhMgBr. This demonstrates its utility in organic synthesis and the preparation of complex molecular structures.
Used in the Formation of Anthranilonitriles:
7-BROMO-1H-INDOLE-2,3-DIONE is also used in the synthesis of anthranilonitriles through the fragmentation of isatin oxime triflates. This process is facilitated by DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) and involves hydrolytic work-up, showcasing the compound's role in the preparation of nitrogen-containing heterocycles.
Check Digit Verification of cas no
The CAS Registry Mumber 20780-74-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,0,7,8 and 0 respectively; the second part has 2 digits, 7 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 20780-74:
(7*2)+(6*0)+(5*7)+(4*8)+(3*0)+(2*7)+(1*4)=99
99 % 10 = 9
So 20780-74-9 is a valid CAS Registry Number.
InChI:InChI=1/C8H4BrNO2/c9-5-3-1-2-4-6(5)10-8(12)7(4)11/h1-3H,(H,10,11,12)
20780-74-9Relevant articles and documents
Indirubin core structure of glycogen synthase kinase-3 inhibitors as novel chemotype for intervention with 5-lipoxygenase
Pergola, Carlo,Gaboriaud-Kolar, Nicolas,Jest?dt, Nadine,K?nig, Stefanie,Kritsanida, Marina,Schaible, Anja M.,Li, Haokun,Garscha, Ulrike,Weinigel, Christina,Barz, Dagmar,Albring, Kai F.,Huber, Otmar,Skaltsounis, Alexios L.,Werz, Oliver
, p. 3715 - 3723 (2014/05/20)
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.
