42816-53-5

Basic information

• Product Name: 5-AMINOISATIN
• Synonyms: 5-AMINOISATIN;5-Amino-1H-indole-2,3-dione;5-Aminoindoline-2,3-dione
• CAS NO: 42816-53-5
• Molecular Formula: C₈H₆N₂O₂
• Molecular Weight: 162.15
• Product Categories: Indane/Indanone and Derivatives
• Mol File: 42816-53-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: >260℃
• Appearance: /
• Density: 1.476
• Storage Temp.: 2-8°C(protect from light)
• PKA: 9.54±0.20(Predicted)
• CAS DataBase Reference: 5-AMINOISATIN(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMINOISATIN(42816-53-5)
• EPA Substance Registry System: 5-AMINOISATIN(42816-53-5)

Safety Data

• Hazardous Substances Data: 42816-53-5(Hazardous Substances Data)

Usage

Definition

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

Upstream product

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

Downstream Products

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

Relevant articles and documents

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.

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.

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.