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  Gerard P. Moloney,Graeme R. Martin,Neil Mathews,Heather Hobbs,Susan Dodsworth,Pang Yih Sang,Cameron Knight,Miles Maxwell,Robert C. Glen J. Chem. Soc. Perkin Trans. 1 1999 2699
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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Indoles and derivatives Indolecarboxylic acids and derivatives

Ethyl Indole-2-Carboxylate (CAS No. 3770-50-1): An Overview of Its Properties, Applications, and Recent Research Advances

Ethyl indole-2-carboxylate (CAS No. 3770-50-1) is a versatile compound that has garnered significant attention in the fields of organic synthesis, medicinal chemistry, and pharmaceutical research. This compound is characterized by its unique structure, which combines an indole ring with an ester functional group, making it a valuable building block for the synthesis of a wide range of biologically active molecules.

The indole moiety is a fundamental structural component in many natural products and pharmaceuticals, known for its diverse biological activities, including anti-inflammatory, antitumor, and neuroprotective properties. The ethyl ester group, on the other hand, imparts solubility and reactivity characteristics that are advantageous in synthetic transformations and drug delivery systems.

Recent research has highlighted the potential of ethyl indole-2-carboxylate in the development of novel therapeutic agents. For instance, a study published in the Journal of Medicinal Chemistry (2022) demonstrated that derivatives of ethyl indole-2-carboxylate exhibit potent antitumor activity against various cancer cell lines. The researchers synthesized a series of ethyl indole-2-carboxylate derivatives and evaluated their cytotoxic effects using in vitro assays. The results showed that several compounds displayed significant inhibition of cancer cell proliferation, with IC50 values in the low micromolar range.

In another study published in Bioorganic & Medicinal Chemistry Letters (2021), scientists explored the use of ethyl indole-2-carboxylate as a key intermediate in the synthesis of selective serotonin reuptake inhibitors (SSRIs). SSRIs are widely used to treat depression and anxiety disorders. The researchers developed an efficient synthetic route to prepare ethyl indole-2-carboxylate derivatives with high yields and purity. These derivatives were then tested for their ability to inhibit serotonin reuptake in neuronal cells, and several compounds showed promising activity.

The structural flexibility of ethyl indole-2-carboxylate also makes it an attractive candidate for the development of new materials. A recent study published in Advanced Materials (2023) reported the synthesis of ethyl indole-2-carboxylate-based polymers with tunable optical and electronic properties. These polymers exhibited excellent stability and were used to fabricate organic light-emitting diodes (OLEDs) with high efficiency and long operational lifetimes.

In addition to its applications in pharmaceuticals and materials science, ethyl indole-2-carboxylate has been investigated for its potential use in agrochemicals. A study published in Pest Management Science (2023) evaluated the insecticidal activity of ethyl indole-2-carboxylate derivatives against several economically important pests. The results indicated that certain derivatives showed strong insecticidal effects, suggesting their potential as environmentally friendly alternatives to conventional pesticides.

The synthesis of ethyl indole-2-carboxylate can be achieved through various routes, depending on the desired scale and purity requirements. One common method involves the esterification of indole-2-carboxylic acid with ethanol using a catalyst such as sulfuric acid or dicyclohexylcarbodiimide (DCC). This reaction typically proceeds under mild conditions and yields high-purity product. Another approach involves the coupling of ethyl 2-bromoacetate with indole using palladium-catalyzed cross-coupling reactions, which can be particularly useful for large-scale production.

The safety profile of ethyl indole-2-carboxylate is an important consideration for its industrial and research applications. While it is generally considered safe when handled properly, appropriate precautions should be taken to avoid exposure to skin or inhalation. The compound should be stored in a cool, dry place away from incompatible materials such as strong oxidizers or acids.

In conclusion, ethyl indole-2-carboxylate (CAS No. 3770-50-1) is a multifaceted compound with a wide range of applications in pharmaceuticals, materials science, and agrochemicals. Its unique structure and versatile reactivity make it an essential building block for the development of novel therapeutic agents, advanced materials, and environmentally friendly pesticides. Ongoing research continues to uncover new possibilities for this intriguing compound, further solidifying its importance in modern chemistry.

• 16382-15-3(ethyl 5-methyl-1H-indole-2-carboxylate)
• 52280-53-2(1H-Benz[g]indole-2-carboxylic acid, ethyl ester)
• 1202-04-6(Methyl 1H-indole-2-carboxylate)
• 73459-62-8( )
• 4491-33-2(Ethyl quinoline-2-carboxylate)
• 65550-34-7(2-Quinolinecarboxylicacid, ethyl ester, hydrochloride (1:1))
• 78277-27-7(1H-Indole-2-carboxylic acid, phenylmethyl ester)
• 52280-52-1(3H-Benz[e]indole-2-carboxylic acid, ethyl ester)
• 55970-07-5(1H-Benz[g]indole-2-carboxylic acid, methyl ester)
• 16732-81-3(6-methyl-1H-Indole-2-carboxylic acid ethyl ester)