250355-46-5

Usage

Structure

1H-Indole-3-carboxylic acid, 1-ethyl-, methyl ester

Type

Chemical compound

Origin

Naturally occurring compound found in various plants

Applications

+ Pharmaceutical industry (due to reported anti-inflammatory properties)
+ Agricultural industry (due to reported antifungal and plant growth promoting properties)
+ Building block in the synthesis of various bioactive compounds

Note

Further research is needed to fully understand its potential uses and effects.

Upstream product

• 201230-82-2 carbon monoxide 
• 250355-39-6 methyl 1-(2-iodoethyl)-1H-indole-3-carboxylate 
• 942-24-5 3-methoxycarbonylindole 
• 250355-37-4 methyl 1-(2-chloroethyl)-1H-indole-3-carboxylate 
• 75-03-6 ethyl iodide 
• 74-96-4 ethyl bromide 
• 64-67-5 diethyl sulfate 
• 771-50-6 1H-indole-3-carboxylic acid 

Downstream Products

• 885524-96-9 C₁₃H₁₅NO₂ 
• 1170114-68-7 C₁₈H₁₅N₃O 
• 1442421-83-1 C₁₈H₁₄FN₃O 
• 1442421-84-2 C₁₈H₁₄ClN₃O 
• 1442421-85-3 C₁₈H₁₄IN₃O 
• 1442421-86-4 C₁₈H₁₄ClN₃O 
• 1442421-87-5 C₁₈H₁₄N₄O₃ 
• 1442421-89-7 C₁₈H₁₄ClN₃O 
• 1442421-90-0 C₁₈H₁₄BrN₃O 
• 1442421-91-1 C₁₈H₁₄N₄O₃ 
• 1442421-92-2 C₁₉H₁₇N₃O 
• 1442421-93-3 C₁₉H₁₇N₃O₂ 
• 1442421-94-4 C₂₀H₁₉N₃O 
• 1442421-95-5 C₂₁H₂₁N₃O₄ 

Relevant academic research and scientific papers

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.

Synthesis and biological evaluation of novel indole derivatives containing sulfonamide scaffold as potential tubulin inhibitor

Microtubule-targeted drugs play a critical role in various types of cancer therapy worldwide. In our study, a series of novel indole derivatives containing a sulfonamide scaffold were designed, synthesized and biologically evaluated as potential tubulin p

Synthesis and antifungal activity of 3-(1,3,4-oxadiazol-5-yl)-indoles and 3-(1,3,4-oxadiazol-5-yl)methyl-indoles

On the basis of the principle of combination of active structural moieties, a modified and efficient synthetic method for three series of novel indole-based 1,3,4-oxadiazoles is described. Bioassays conducted at Syngenta showed that several of the synthesized compounds exhibit higher antifungal activity than pimprinine, the natural product which inspired this synthesis. Two main structural alterations were found to broaden the spectrum of biological activity in most cases. Compounds 3g, 6c, 6e, 6h, 9d, 9e, 9h and 9m (Fig. 1) were identified as the most active on the biological assays, and will be studied further.

Discovery of trans-4-[1-[[2,5-dichloro-4-(1-methyl-3-indolylcarboxamido) phenyl]acetyl]-(4S)-methoxy-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylic acid: An orally active, selective very late antigen-4 antagonist

We have focused on optimization of the inadequate pharmacokinetic profile of trans-4-substituted cyclohexanecarboxylic acid 5, which is commonly observed in many small molecule very late antigen-4 (VLA-4) antagonists. We modified the lipophilic moiety in 5 and found that reducing the polar surface area of this moiety results in improvement of the PK profile. Consequently, our efforts have led to the discovery of trans-4-[1-[[2,5-dichloro-4-(1-methyl-3- indolylcarboxamido)phenyl]acetyl]-(4S)-methoxy-( 2S)-pyrrolidinylmethoxy] cyclohexanecarboxylic acid (14e) with potent activity (IC50 = 5.4 nM) and significantly improved bioavailability in rats, dogs, and monkeys (100%, 91%, 68%), which demonstrated excellent oral efficacy in murine and guinea pig models of asthma. Based on its overall profile, compound 14e was progressed into clinical trails. In a single ascending-dose phase I clinical study, compound 14e exhibited favorable oral exposure as expected and had no serious adverse events.

NICOTINIC ACETYLCHOLINE RECEPTOR MODULATORS

The present invention provides compounds of formula (I) and compositions thereof, methods of making them, and methods of using them to modulate alpha7 nicotinic acetylcholine receptors and/or to treat any of a variety of disorders, diseases, and conditions. Provided compounds can affect, among other things, neurological, psychiatric and/or inflammatory system.

Design, synthesis, and biological activity of potent and selective inhibitors of mast cell tryptase

A new series of novel mast cell tryptase inhibitors is reported, which features the use of an indole structure as the hydrophobic substituent on a m-benzylaminepiperidine template. The best members of this series display good in vitro activity and excellent selectivity against other serine proteases.

Chemical compounds

Provided herein are novel and useful compounds having a tryptase inhibition activity, pharmaceutical compositions comprising such compounds, and methods treating subjects suffering from a condition, disease, or disorder that can be ameliorated by the administration of an inhibitor of tryptase, e.g., asthma and inflammatory diseases, to name only a few.

A tandem carbonylation/cyclization radical process of 1-(2-iodoethyl)indoles and pyrrole

The AIBN-induced radical reaction of 1-(2-iodoethyl)indoles and pyrroles with Bu3SnH under 80 atm of CO was examined. Carbon monoxide was efficiently trapped by an alkyl radical to form an acyl radical which underwent intramolecular addition to the aromatic system to produce bicyclic aromatic ketones after in situ oxidation.