776-41-0

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl indole-3-carboxylate is used as a reactant for the preparation of indole-based heterocycles, which are essential in the synthesis of indole-based p38 inhibitors and gramines. These compounds play a crucial role in the development of new drugs for various medical applications.
Used in Neuroscience Research:
In the field of neuroscience, ethyl indole-3-carboxylate is used as a glycine receptor ligand. This application aids in the study of the nervous system and the development of treatments for neurological disorders.
Used in Inflammation and Allergy Research:
Ethyl indole-3-carboxylate is also used as an inhibitor of human 5-lipoxygenase, an enzyme involved in the production of leukotrienes, which are associated with inflammation and allergy. This application contributes to the development of anti-inflammatory and anti-allergic drugs.
Used in Antimicrobial Applications:
Furthermore, ethyl indole-3-carboxylate is utilized as an antimicrobial agent, demonstrating its potential in the development of new antibiotics and antifungal agents to combat drug-resistant infections.

InChI:InChI=1/C11H11NO2/c1-2-14-11(13)9-7-12-10-6-4-3-5-8(9)10/h3-7,12H,2H2,1H3

Upstream product

• 59496-25-2 Indole-3-carbonyl chloride 
• 541-41-3 chloroformic acid ethyl ester 
• 64-17-5 ethanol 
• 30030-90-1 2,2,2-trichloro-1-(1H-indol-3-yl)ethan-1-one 
• 13307-67-0 ethyl 1H-indole-1-carboxylate 
• 352667-81-3 3-benzotriazol-1-yl-acrylic acid ethyl ester 
• 187753-58-8 ethyl 2,3-di(phenylamino)propenoate 
• 771-50-6 1H-indole-3-carboxylic acid 
• 75-03-6 ethyl iodide 
• 623-73-4 diazoacetic acid ethyl ester 
• 529-23-7 o-aminobenzaldehyde 
• 586-96-9 Nitrosobenzene 
• 120-72-9 indole 
• 615-43-0 2-iodophenylamine 

Downstream Products

• 15317-58-5 1H-indole-3-carboxylic acid hydrazide 
• 91090-95-8 6-nitro-indole-3-carboxylic acid ethyl ester 
• 128915-34-4 1-Benzoylindol-3-carbonsaeureethylester 
• 128915-36-6 1-Carbobenzoxyindol-3-carbonsaeureethylester 
• 128915-35-5 1-(3,5-Dinitrobenzoyl)-indol-3-carbonsaeureethylester 
• 56559-61-6 ethyl 1-benzyl-1H-indole-3-carboxylate 
• 73053-97-1 N-[2-(1H-indol-3-yl)-2-oxoethyl]-2-phenylacetamide 
• 73053-91-5 34N 
• 13640-26-1 pimprinine 
• 73053-81-3 pimprinethine 
• 73053-85-7 3-(2-benzyl-1,3-oxazol-5-yl)-1H-indole 
• 854923-38-9 5,6-dibromo-1H-indole 
• 4769-96-4 6-nitroindole 
• 876479-95-7 6-amino-indole-3-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Convenient method of synthesizing 3-ethoxycarbonyl indoles

We have developed a convenient two-step procedure for the synthesis of 3-ethoxycarbonyl indoles from commercially available materials. The two-step procedure involves the synthesis of 2-aryl-3-hydroxypropenoic acid ester, followed by a catalytic reduction

Development and Profiling of Inverse Agonist Tools for the Neuroprotective Transcription Factor Nurr1

The ligand-sensing transcription factor nuclear receptor related 1 (Nurr1) evolves as an appealing target to treat neurodegenerative diseases. Despite its therapeutic potential observed in various rodent models, potent modulators for Nurr1 are lacking as pharmacological tools. Here, we report the structure-activity relationship and systematic optimization of indole-based inverse Nurr1 agonists. Optimized analogues decreased the receptor's intrinsic transcriptional activity by up to more than 90% and revealed preference for inhibiting Nurr1 monomer activity. In orthogonal cell-free settings, we detected displacement of NCoRs and disruption of the Nurr1 homodimer as molecular modes of action. The inverse Nurr1 agonists reduced the expression of Nurr1-regulated genes in T98G cells, and treatment with an inverse Nurr1 agonist mimicked the effect of Nurr1 silencing on interleukin-6 release from LPS-stimulated human astrocytes. The indole-based inverse Nurr1 agonists valuably extend the toolbox of Nurr1 modulators to further probe the role of Nurr1 in neuroinflammation, cancer, and beyond.

A general and scalable synthesis of polysubstituted indoles

A consecutive 2-step synthesis of N-unprotected polysubstituted indoles bearing an electron-withdrawing group at the C-3 position from readily available nitroarenes is reported. The protocol is based on the [3,3]-sigmatropic rearrangement of N-oxyenamines generated by the DABCO-catalyzed reaction of N-arylhydroxylamines and conjugated terminal alkynes, and delivers indoles endowed with a wide array of substitution patterns and topologies.

Amination/Cyclization Cascade by Acid-Catalyzed Activation of Indolenine for the One-Pot Synthesis of Phaitanthrin E

We have developed a concise one-pot synthesis of phaitanthrin E derivatives, where simple starting materials undergo an acid-catalyzed intermolecular amination/intramolecular cyclization cascade.

Catalytic synthesis method of indole compounds

The invention discloses a catalytic synthesis method of indole compounds.The method includes the following steps of firstly, conducting stirring reaction on ortho-nitrostyrolene or derivatives of ortho-nitrostyrolene, bis(pinacolato)diboron, alkali and low-grade saturated monohydric alcohol under the atmosphere of nitrogen; secondly, cooling the reaction product in the first step to the room temperature, adding ethyl acetate to be sufficiently mixed, and washing with ethyl acetate after filtering; thirdly, spin-drying low-grade saturated monohydric alcohol in an organic phase of the material obtained in the second step, passing through a silica gel column, and drip washing the silica gel column with eluent composed of petroleum ether and ethyl acetate to obtain pure products, namely, the indole compounds.By means of the method, under the neutral conditions, bis(pinacolato)diboron low in price serves as the raw material, friendly low-grade saturated monohydric alcohol serves as the solvent, the indole compounds are obtained through simple operation, the raw materials are low in price and easy to obtain, efficiency and safety are high, and wide expandability and good industrial application prospects are achieved.

Photochemistry of benzotriazoles: Generation of 1,3-diradicals and intermolecular cycloaddition as a new route toward indoles and dihydropyrrolo[3,4-b]indoles

Irradiation of benzotriazoles 1a-e at λ = 254 nm in acetonitrile solution generated the corresponding 1,3-diradicals which underwent intermolecular cycloaddition with maleimides to afford the corresponding dihydropyrrolo[3,4-b]indoles and with acetylene derivatives to afford indoles as the major products. This offers an interesting and simple access to such ring systems of potential synthetic and biological interest. The structures of the photoproducts were established spectroscopically and by single crystal X-ray crystallography.

A series of 2-arylamino-5-(indolyl)-1,3,4-thiadiazoles as potent cytotoxic agents

A series of 2-arylamino-5-(indolyl)-1,3,4-thiadiazoles 6a-v were prepared and studied for their anticancer activity against selected human cancer cell lines. The reaction of indolylhydrazides 3a-h with a variety of aryl isothiocyanates 4 afforded the key intermediate thiosemicarbazides 5a-v, which upon treatment with acetyl chloride produced the 2-arylamino-5-(indolyl)-1,3,4- thiadiazoles 6a-v in good yields. Most of the synthesized compounds showed selective cytotoxicity towards human breast cancer cell line (MDA-MB-231). Of the synthesized 2-arylamino-5-(indolyl)-1,3,4-thiadiazoles, compound 6f is the most potent towards tested cancer cell lines (IC50 = 0.15-1.18 μM).

Novel bis(indolyl)hydrazide-hydrazones as potent cytotoxic agents

A series of bis(indolyl) hydrazide-hydrazones 5a-n were synthesized and evaluated for their cytotoxicity against selected human cancer cell lines. The reaction of indole-3-carboxaldehyde 2 with indole-3-carbohydrazide 4 in presence of catalytic amount of acetic acid afforded 5a-n in good yields. Among the synthesized bis(indolyl)hydrazide-hydrazones, the compound 5b with N-(p-chlorobenzyl) and bromo substituents was found to be the most potent against multiple cancer cell lines (IC50 = 1.0 μM, MDA-MB-231). The compound 5k exhibited selective cytotoxicity against breast cancer cell line MCF7 (IC50 = 3.1 μM).