42816-53-5

Usage

Definition

ChEBI: Isatin substituted at C-5 by an amino group.

Upstream product

• 611-09-6 5-nitroisatin 
• 75591-28-5 N-(2,3-dioxoindolin-5-yl)acetamide 
• 860542-79-6 N-(3-hydroxy-2-oxo-indolin-5-yl)-acetamide 
• 38423-73-3 1-acetylamino-4-(2-hydroxyimino-acetylamino)-benzene 
• 122-80-5 N-acetyl-p-phenylenediamine 
• 69951-01-5 2-iodo-1,4-phenylenediamine 

Downstream Products

• 222035-40-7 4-[N'-(5-Amino-2-oxo-1,2-dihydro-indol-3-ylidene)-hydrazino]-benzenesulfonamide hydrochloride 
• 20876-36-2 5-amino-1,3-dihydro-2H-indol-2-one 
• 1427789-19-2 C₁₃H₁₀N₂O₂ 
• 867376-36-1 C₁₆H₁₂N₂O₃ 
• 116569-09-6 5-Hydroxyisatin 

Relevant academic research and scientific papers

Discovery of an eIF4A Inhibitor with a Novel Mechanism of Action

Increased protein synthesis is a requirement for malignant growth, and as a result, translation has become a pharmaceutical target for cancer. The initiation of cap-dependent translation is enzymatically driven by the eukaryotic initiation factor (eIF)4A, an ATP-powered DEAD-box RNA-helicase that unwinds the messenger RNA secondary structure upstream of the start codon, enabling translation of downstream genes. A screen for inhibitors of eIF4A ATPase activity produced an intriguing hit that, surprisingly, was not ATP-competitive. A medicinal chemistry campaign produced the novel eIF4A inhibitor 28, which decreased BJAB Burkitt lymphoma cell viability. Biochemical and cellular studies, molecular docking, and functional assays uncovered that 28 is an RNA-competitive, ATP-uncompetitive inhibitor that engages a novel pocket in the RNA groove of eIF4A and inhibits unwinding activity by interfering with proper RNA binding and suppressing ATP hydrolysis. Inhibition of eIF4A through this unique mechanism may offer new strategies for targeting this promising intersection point of many oncogenic pathways.

Dansyl-NA3conjugates for glycoprotein detection through fluorescent tagging and native gel electrophoresis

A new approach to the fluorescent labelling of glycoproteins was developed utilizing the aldehyde-reactiveN-amino anthranilic acid (NA3) moiety linked to a dansyl fluorophore. The presented synthetic method is based on the conjugation of isatin as a “masked” anthranilic acid, thus eliminating the need for the use of protecting groups. Fluorescence properties and chemical stability of the prepared molecules were evaluated, resulting in the selection of a conjugate directly connecting the dansyl moiety and aldehyde-reactive NA3through a sulfonamide linkage for further studies. NaIO4-mediated oxidation of the glycosylated protein fetuin followed by rapid fluorescent tagging and native gel electrophoresis afforded glycoprotein detection. The detection limit of the described method was 18 ng of protein, providing sensitivity sufficient for the detection of abundant glycosylated serum proteins.

A Palladium-Catalyzed Double Carbonylation Approach to Isatins from 2-Iodoanilines

A high-yielding procedure for the synthesis of isatins has been developed. Sequential Pd-catalyzed double carbonylation of 2-iodoanilines with near stoichiometric amounts of CO followed by acid-promoted cyclization readily affords an array of isatins. The conversion of 2-iodoanilines to isatins in good to excellent yields was found to proceed with good functional group tolerance. This protocol proved adaptable to 13C-isotope labeling of isatins, which was extended to the synthesis of the 13C-isotope labeled antiviral drug metisazone and the experimental anti-schizophrenia drug ML137.

Synthesis of novel 5-substituted indirubins as protein kinases inhibitors

In an effort to identify new pharmacological inhibitors of disease-relevant protein kinases with increased potency and selectivity, we synthesized and evaluated new 5-substituted indirubins. The effects of 34 indirubin derivatives on CDK1/cyclin B, CDK5/p25, and GSK-3, as well as on SH-SY5Y human neuroblastoma cell survival, were investigated.

PTEN INHIBITORS

The therapeutic use of inhibitors of PTEN activity in the treatment of PTEN-mediated diseases, conditions, and injuries is disclosed.

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.