5-Methoxyisatin
[CAS# 39755-95-8]

Identification

• Classification: Biochemical >> Biochemical reagent >> Biological dye
• Name: 5-Methoxyisatin
• Synonyms: 5-Methoxy-1H-indole-2,3-dione
• Molecular Formula: C₉H₇NO₃
• Molecular Weight: 177.16
• CAS Registry Number: 39755-95-8
• EC Number: 670-372-2
• SMILES: COC1=CC2=C(C=C1)NC(=O)C2=O

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Melting point: 197-199 ºC (Expl.)
• Index of Refraction: 1.585, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319
Eye irritation	Eye Irrit.	2	H319

Discovory and Applicatios

5-Methoxyisatin is a chemical compound belonging to the class of isatins, which are characterized by the presence of an indole-2,3-dione structure. It is a derivative of isatin with a methoxy group (-OCH₃) attached to the fifth position of the aromatic ring. Isatins, including 5-methoxyisatin, are important in both synthetic and medicinal chemistry due to their diverse biological activities and utility in chemical synthesis.

The compound 5-methoxyisatin has been studied for its role as an intermediate in organic synthesis, where it can be further modified to create more complex molecules. Isatins themselves are valuable building blocks in the production of pharmaceuticals, dyes, and other organic compounds due to their reactive functional groups. The methoxy group in 5-methoxyisatin influences the reactivity and properties of the molecule, making it useful in the synthesis of a variety of derivatives with potentially useful biological activities.

5-Methoxyisatin has been investigated for its biological activities, which include antimicrobial, anticancer, and anti-inflammatory properties. Research has shown that isatins, including 5-methoxyisatin, exhibit interactions with enzymes, receptors, and other biomolecules, making them of interest in drug design. The compound has been explored for its potential therapeutic applications, particularly in the development of novel agents for the treatment of infections and cancer.

In addition to its biological activity, 5-methoxyisatin is used as a starting material in the synthesis of various derivatives, which are explored for their pharmacological properties. For example, it can be used to create compounds that inhibit specific enzymes or modulate cellular pathways, which may be useful in the treatment of various diseases.

While 5-methoxyisatin itself may not be a widely used commercial pharmaceutical, its derivatives are of significant interest in research aimed at developing new therapeutic agents. As part of the isatin family, it contributes to a broader understanding of the biological and chemical properties of isatin derivatives, which continue to be an important area of study in medicinal chemistry.

In summary, 5-methoxyisatin is a derivative of isatin that plays an important role in organic synthesis and has been studied for its biological activities. Its applications include use as an intermediate in the synthesis of more complex molecules and as a potential source of compounds with antimicrobial, anticancer, and anti-inflammatory effects. Through its contribution to the development of new pharmaceutical agents, 5-methoxyisatin continues to be a compound of interest in chemical and medicinal research.

References

2007. In vitro cytotoxicity evaluation of some substituted isatin derivatives. Bioorganic & Medicinal Chemistry, 15(2).
DOI: 10.1016/j.bmc.2006.10.035

2017. Assessment of 5-substituted Isatin as Surface Recognition Group: Design, Synthesis, and Antiproliferative Evaluation of Hydroxamates as Novel Histone Deacetylase Inhibitors. Pharmaceutical Chemistry Journal, 51(5).
DOI: 10.1007/s11094-017-1616-1

2024. Synthesis, structure elucidation, antioxidant properties, and theoretical calculations of new Schiff bases-isatin derivatives. Research on Chemical Intermediates, 50(8).
DOI: 10.1007/s11164-024-05318-1