306325-13-3

Basic information

• Product Name: 6-BROMO-5-METHYLISATIN
• Synonyms: AG-690/08980048;ARONIS016716;BIM-0014096.P001;CBMicro_014209;STK042825;ZINC02052963;6-BROMO-5-METHYLISATIN;6-bromo-5-methyl-indoline-2,3-dione
• CAS NO: 306325-13-3
• Molecular Formula: C₉H₆BrNO₂
• Molecular Weight: 240.05
• Product Categories: Indane/Indanone and Derivatives
• Mol File: 306325-13-3.mol

Chemical Properties

• Appearance: /
• Density: 1.714±0.06 g/cm3(Predicted)
• PKA: 8.84±0.20(Predicted)
• CAS DataBase Reference: 6-BROMO-5-METHYLISATIN(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-5-METHYLISATIN(306325-13-3)
• EPA Substance Registry System: 6-BROMO-5-METHYLISATIN(306325-13-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 306325-13-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
6-BROMO-5-METHYLISATIN is used as a key intermediate in organic synthesis for the production of various pharmaceuticals and organic compounds. Its unique structure allows for versatile chemical reactions, making it a valuable component in the synthesis of complex organic molecules.
Used in Biological Studies as a Fluorescent Label:
Leveraging its fluorescent properties, 6-BROMO-5-METHYLISATIN is employed as a fluorescent label in biological studies. It aids researchers in visualizing and tracking specific biomolecules, cells, or cellular processes, thereby enhancing the understanding of biological systems and mechanisms.
Used in Pharmaceutical Development:
6-BROMO-5-METHYLISATIN is studied for its potential pharmacological activities, including its anti-inflammatory and anti-cancer properties. Its ability to modulate various biological pathways makes it a promising candidate for the development of new drugs to treat inflammatory and cancerous conditions.
Used in Material Science for New Material Development:
6-Bromo-5-methylisatin has been investigated for its potential use in the development of new materials for various applications. Its unique chemical and physical properties can contribute to the creation of innovative materials with enhanced performance characteristics in different industries.

Upstream product

• 7745-91-7 3-bromo-4-methylaniline 
• 147149-83-5 N-(3-bromo-4-methyl-phenyl)-2-hydroxyimino-acetamide 

Downstream Products

• 356524-80-6 C₁₉H₁₈BrN₃O₅ 

Relevant articles and documents

Utilizing Solubility differences to achieve regiocontrol in the synthesis of substituted quinoline-4-carboxylic acids

A practical method for the regiocontrolled synthesis of substituted quinoline-4-carboxylic acids is described. Solubility differences between the product quinoline regioisomers enable their facile separation, thus avoiding any challenging chromatographic purifications and allowing access to highly substituted quinoline compounds in three steps from commercially available anilines.

INDIRUBIN-TYPE COMPOUNDS, COMPOSITIONS, AND METHODS FOR THEIR USE

Compounds and compositions including 6-bromo-indirubin, 5-amino-indirubin and N-methyl-indirubins and related indirubin derivatives are provided that are useful as selective modulators of glycogen synthase kinase-3, cyclin-dependent protein kinases or aryl hydrocarbon receptors. Methods of inhibiting or modulating cell growth or cell cycling are provided using the compounds of the invention. In other aspects, compounds and methods for the treatment of protozoan-mediated diseases, Alzheimer's disease and diabetes are provided.

Structural Basis for the Synthesis of Indirubins as Potent and Selective Inhibitors of Glycogen Synthase Kinase-3 and Cyclin-Dependent Kinases

Pharmacological inhibitors of glycogen synthase kinase-3 (GSK-3) and cyclin-dependent kinases have a promising potential for applications against several neurodegenerative diseases such as Alzheimer's disease. Indirubins, a family of bis-indoles isolated from various natural sources, are potent inhibitors of several kinases, including GSK-3. Using the cocrystal structures of various indirubins with GSK-3β, CDK2 and CDK5/p25, we have modeled the binding of indirubins within the ATP-binding pocket of these kinases. This modeling approach provided some insight into the molecular basis of indirubins' action and selectivity and allowed us to forecast some improvements of this family of bis-indoles as kinase inhibitors. Predicted molecules, including 6-substituted and 5,6-disubstituted indirubins, were synthesized and evaluated as CDK and GSK-3 inhibitors. Control, kinase-inactive indirubins were obtained by introduction of a methyl substitution on N1.

Design of thymidylate synthase inhibitors using protein crystal structures: The synthesis and biological evaluation of a novel class of 5- substituted quinazolinones

The design, synthesis, and biological evaluation of a new class of inhibitors of thymidylate synthase (TS) is described. The molecular design was carried out by a repetitive crystallographic analysis of protein-ligand structures. At the onset of this project, we focused on the folate cofactor binding site of a high-resolution ternary crystal complex of Escherichia coli TS, 5'-fluorodeoxyuridylate (5-FdUMP) and a classical glutamate-containing folic acid analog. A preliminary ternary crystal structure of a novel compound was successfully solved. Upon analysis of this initial complex, further structural elaborations were made, and a series of active 5- (arylthio)quinazolinones was developed. The synthetic strategy was based on the displacement of a halogen at the 5-position of a quinazolinone by various arylthioanions. The compounds were tested for inhibition of purified E. coli and/or human TS, and were assayed for cytotoxicity against three tumor cell lines in vitro. Significant thymidine protection effects were observed with several of the inhibitors, indicating that TS was the intracellular locus of activity.