147149-84-6

Usage

Uses

Used in Pharmaceutical Industry:
4-Bromo-5-methyl-2,3-indolinedione is used as a chemical reagent for the production of Nolatrexed Dihydrochloride, a potent anticancer agent. It contributes to the synthesis process by acting as a key intermediate, enabling the development of effective cancer treatments.

InChI:InChI=1/C9H6BrNO2/c1-4-2-3-5-6(7(4)10)8(12)9(13)11-5/h2-3H,1H3,(H,11,12,13)

Upstream product

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

Downstream Products

• 1292780-40-5 C₁₈H₁₃BrN₄O₃S 
• 147149-88-0 methyl 2-amino-6-bromo-5-methylbenzoate 
• 328026-66-0 N'-(4-bromo-5-methyl-2-oxoindolin-3-ylidene)-3,4,5-trimethoxybenzohydrazide 
• 147150-03-6 Diethyl N-<4-<(2-amino-6-methyl-4-oxo-3,4-dihydroquinazolin-5-yl)sulfanyl>benzoyl>-L-glutamate 
• 147150-02-5 Diethyl-N-<4-<(2,6-dimethyl-4-oxo-3,4-dihydroquinazolin-5-yl)sulfanyl>benzoyl>-L-glutamate 
• 147150-00-3 4-((2-amino-6-methyl-4-oxo-3,4-dihydroquinazolin-5-yl)sulfanyl)benzoic acid methyl ester 
• 152946-39-9 4-((2,6-dimethyl-4-oxo-3,4-dihydroquinazolin-5-yl)sulfanyl)benzoic acid methyl ester 
• 147150-01-4 4-(2-Amino-6-methyl-4-oxo-3,4-dihydro-quinazolin-5-ylsulfanyl)-benzoic acid 
• 147149-69-7 4-[(3,4-Dihydro-2,6-dimethyl-4-oxo-5-quinazolinyl)thio]-benzoic acid 
• 147149-89-1 2-amino-5-bromo-6-methyl-3-H-quinazolin-4-one 
• 502607-48-9 2-guanidino-5-bromo-3,4-dihydro-6-methylquinazolin-4-one 
• 147149-85-7 6-amino-2-bromo-3-methyl-benzoic acid 

Relevant academic research and scientific papers

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.