210303-07-4

Basic information

• Product Name: (3Z)-3-(1H-pyrrol-2-ylmethylidene)-1,3-dihydro-2H-indol-2-one
• Synonyms: 2H-indol-2-one, 1,3-dihydro-3-(1H-pyrrol-2-ylmethylene)-, (3Z)-
• CAS NO: 210303-07-4
• Molecular Formula: C₁₃H₁₀N₂O
• Molecular Weight: 210.2313
• Mol File: 210303-07-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 490.7°C at 760 mmHg
• Flash Point: 250.6°C
• Density: 1.337g/cm³
• Vapor Pressure: 8.94E-10mmHg at 25°C
• Refractive Index: 1.724
• CAS DataBase Reference: (3Z)-3-(1H-pyrrol-2-ylmethylidene)-1,3-dihydro-2H-indol-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3Z)-3-(1H-pyrrol-2-ylmethylidene)-1,3-dihydro-2H-indol-2-one(210303-07-4)
• EPA Substance Registry System: (3Z)-3-(1H-pyrrol-2-ylmethylidene)-1,3-dihydro-2H-indol-2-one(210303-07-4)

Safety Data

• Hazardous Substances Data: 210303-07-4(Hazardous Substances Data)

Usage

Description

(3Z)-3-(1H-pyrrol-2-ylmethylidene)-1,3-dihydro-2H-indol-2-one, commonly known as isatin, is a heterocyclic organic compound with the molecular formula C8H7NO2. It features a unique structure that includes a pyrrole ring fused to an oxindole. (3Z)-3-(1H-pyrrol-2-ylmethylidene)-1,3-dihydro-2H-indol-2-one has garnered significant interest due to its diverse biological activities and potential applications in various fields.

Uses

Used in Pharmaceutical Development:
Isatin is utilized as a key component in the development of pharmaceutical drugs, capitalizing on its antimicrobial, anti-inflammatory, and anticancer properties. Its multifaceted biological activities make it a promising candidate for treating a range of diseases and disorders.
Used in Organic Synthesis:
As a building block in organic synthesis, isatin contributes to the creation of various complex organic compounds. Its unique structure allows it to be a valuable intermediate in the synthesis of a wide array of molecules, enhancing the scope of chemical research and development.
Used as a Dye and Indicator:
Leveraging its characteristic blue color, isatin serves as a dye and indicator in chemical and biological research. Its distinctive hue aids in visual identification and tracking of reactions or processes in laboratory settings, facilitating research and experimentation.

Upstream product

• 1003-29-8 2-pyrrole aldehyde 
• 59-48-3 2-oxoindole 

Relevant articles and documents

Seven 3-methyl-idene-1H-indol-2(3H)-ones related to the multiple-receptor tyrosine kinase inhibitor sunitinib

The solid-state structures of a series of seven substituted 3-methyl-idene-1H-indol-2(3H)-one derivatives have been determined by single-crystal X-ray diffraction and are compared in detail. Six of the structures {(3Z)-3-(1H-pyrrol-2-ylmethyl-idene)-1H-in

Photoinduced Isomerization and Hepatoxicities of Semaxanib, Sunitinib and Related 3-Substituted Indolin-2-ones

3-Substituted indolin-2-ones are an important class of compounds that display a wide range of biological activities. Sunitinib is an orally available multiple tyrosine kinase inhibitor that has been approved by the US Food and Drug Administration (FDA) for the treatment of renal cell cancer. Sunitinib and a related compound, semaxanib, exist as thermodynamically stable Z isomers, which photoisomerize to E isomers in solution. In this study, 17 3-substituted indolin-2-ones were synthesized, and the kinetics of their photoisomerization were studied by 1H NMR spectroscopy. The rate constants for photoisomerization ranged from 0.009 to 0.048 h-1. Selected compounds were tested for cytotoxicity in the TAMH liver cell line. E/Z mixtures of four compounds were also assessed for toxicity in the TAMH and HepG2 cell lines. In some cases, the stereochemically pure drug was more toxic than the E/Z mixtures, but a general statement cannot be made. Our studies show that each stereoisomer could contribute differently to toxicity, suggesting that stereochemical purity issues that could arise from isomerization cannot be ignored.

Kinase inhibitors for the treatment of disease

The present invention relates to organic molecules capable of modulating tyrosine kinase signal transduction in order to regulate, modulate and/or inhibit abnormal cell proliferation.