5-Amino-1H-indole-2,3-dione
[CAS# 42816-53-5]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Indoles
• Name: 5-Amino-1H-indole-2,3-dione
• Synonyms: 5-Aminoisatin
• Molecular Formula: C₈H₆N₂O₂
• Molecular Weight: 162.15
• CAS Registry Number: 42816-53-5
• SMILES: C1=CC2=C(C=C1N)C(=O)C(=O)N2

Properties

• Density: ensity1.5±0.1 g/cm³, Calc.^*
• Index of refraction: 1.683, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

5-Amino-1H-indole-2,3-dione, also known as 5-aminoindole-2,3-dione or simply 5-AI, is a chemical compound that belongs to the indole family, which is a group of heterocyclic compounds containing a fused benzene and pyrrole ring structure. It is an amino-substituted derivative of indole-2,3-dione, a structure found in a variety of biologically active molecules.

This compound has garnered attention for its potential biological activities, particularly in relation to its role in medicinal chemistry and synthetic biology. 5-Amino-1H-indole-2,3-dione serves as a building block or intermediate in the synthesis of various bioactive molecules. The amino group at position 5 of the indole ring system can participate in further chemical modifications, which may enhance its biological properties or enable it to form more complex structures with specific pharmacological activities.

In medicinal chemistry, indole derivatives, including 5-aminoindole-2,3-dione, are often explored for their potential anticancer, antimicrobial, and anti-inflammatory properties. Their ability to interact with biological targets, such as enzymes or receptors, makes them of interest for the development of new therapeutic agents. Specifically, compounds with indole-based scaffolds have been studied for their activity in inhibiting certain enzymes that play a key role in cancer cell proliferation or microbial growth. Additionally, the structure of 5-aminoindole-2,3-dione has potential as a precursor for the synthesis of other indole derivatives with more targeted therapeutic effects.

5-Amino-1H-indole-2,3-dione is also used as a precursor in the synthesis of other heterocyclic compounds that may have improved bioactivity or targeted pharmacological profiles. The indole ring system is a core structural element in many natural products and synthetic drugs, making compounds like 5-aminoindole-2,3-dione valuable in research and drug discovery.

Given its potential applications in the field of medicinal chemistry, further research into the biological activities and chemical modifications of 5-aminoindole-2,3-dione is ongoing. The molecule's ability to undergo various chemical transformations allows for the development of novel compounds with diverse biological functions, and it remains an important structure in the study of indole-based therapeutics.

Though 5-aminoindole-2,3-dione itself is not yet widely used as a commercial drug, its importance in the synthesis of more complex bioactive molecules highlights its potential in future pharmaceutical development. As research continues, the molecule could become a significant component of therapeutic agents targeting various diseases.

References

2020. Interaction of Isatin with Cytochrome P450 Isoenzymes: Investigation by Means of Spectral and Electrochemical Methods The role of Isatin in Cytochromes P450 Ligand-Protein Binding Events. BioNanoScience, 10(1).
DOI: 10.1007/s12668-019-00707-y

2018. Specificity of Isatin Interaction with Cytochromes P450. Biochemistry (Moscow), Supplement Series B: Biomedical Chemistry, 14(2).
DOI: 10.1134/s1990750818020026

2012. Effect of affinity Sorbent on proteomic profiling of isatin-binding proteins of mouse brain. Biochemistry. Biokhimiia, 77(11).
DOI: 10.1134/s0006297912110120