6639-06-1

Usage

Uses

Used in Pharmaceutical Industry:
1-Indolepropionic acid is used as a therapeutic agent for its potential role in managing inflammation and oxidative stress, which are common denominators in various diseases and conditions.
Used in Nutritional Supplements:
It is used as a dietary supplement to support gut health and immune system function, given its potential to promote these aspects of health.
Used in Research and Development:
1-Indolepropionic acid is utilized in scientific research for exploring its potential effects on diabetes, obesity, and neurodegenerative diseases, indicating its use as a subject of study for developing new treatments and interventions.

InChI:InChI=1/C11H11NO2/c13-11(14)6-8-12-7-5-9-3-1-2-4-10(9)12/h1-5,7H,6,8H2,(H,13,14)

Upstream product

• 4414-79-3 3-(1H-indol-1-yl)propanenitrile 
• 120-72-9 indole 
• 3395-91-3 Methyl 3-bromopropionate 
• 26585-38-6 3-(indol-1-yl)propionic acid ethyl ester 
• 221687-62-3 methyl 3-(1H-indol-1-yl)-2-methylpropanoate 
• 76916-49-9 3-(indol-1-yl)propionic acid methyl ester 
• 140-88-5 ethyl acrylate 
• 109-78-4 3-Hydroxypropionitrile 
• 79-10-7 acrylic acid 

Downstream Products

• 351015-67-3 1-(3-hydroxypropyl)-1H-indole-3-carbaldehyde 
• 81250-90-0 3-(2,3-dioxoindolin-1-yl)propanoic acid 

Relevant academic research and scientific papers

Computational and experimental studies of (2,2)-Bis(indol-1-yl- methyl)acetate suggest the importance of the hydrophobic effect in aromatic stacking interactions

To understand the driving forces of aromatic stacking interactions in water, we have performed conformational searches, molecular dynamics simulations, potential of mean force (PMF) and free energy perturbation (FEP) calculations, syntheses, and NMR studies on sodium (2,2)-bis(indol-1-yl- methyl)acetate (1), sodium 3-indol-1-yl-2-methyl-propionate (2), and sodium 3-indol-1-yl-propionate (3). The conformational searches on 1 revealed that the isobutyric acid linker of 1 allows the molecule to adopt the tilted T- shaped stacked, off-center stacked, face-to-face stacked, and nonstacked conformations in a vacuum. The PMF and FEP calculations suggested that the most thermodynamically stable conformers in water are the tilted T-shaped stacked and nonstacked conformers. Independent NMR spectroscopic studies of 1-3 revealed that both the tilted T-shaped stacked and nonstacked conformers are populated in D2O and in d6-DMSO, and they are in a rapid equilibrium. Furthermore, the NMR studies found (i) a larger population of the tilted T, shaped stacked conformation of 1 at 22 °C in D2O than in d6-DMSO and (ii) more different populated stacked conformations of 1 at 60 °C in D2O than in d6-DMSO. One would expect larger populations of the stacked conformations in d6-DMSO, whose dielectric constant is smaller than that of water, if the electrostatic interaction were the only driving force of the aromatic stacking interactions. The results, therefore, suggest that the hydrophobic effect plays an important role in the stacking interaction of 1 in water.

Supramolecular Hydrogels of Indole-Capped Short Peptides as Vaccine Adjuvants

Many materials as immune adjuvant are researched to help raise immnogenicity of subunit vaccines. Among them, peptide-based hydrogels are gradually coming into notice because of their application in drugs delivery, cancer cell inhibition, vaccine adjuvants and detection of important analytes. In this work, we introduced a novel aromatic capping group based on indole to construct short peptide-based supramolecular hydrogelators Indol-GFFY and Indol-GDFDFDY and demonstrated their potential applications as vaccine adjuvants.

CYCLIC AMIDE DERIVATIVES AS INHIBITORS OF 11 - BETA - HYDROXYSTEROID DEHYDROGENASE AND USES THEREOF

The present invention relates to certain amide derivatives that have the ability to inhibit 11-β-hydroxysteroid dehydrogenase type 1 (11β-HSD-1) and which are therefore useful in the treatment of certain disorders that can be prevented or treated by inhibition of this enzyme. In addition the invention relates to the compounds, methods for their preparation, pharmaceutical compositions containing the compounds and the uses of these compounds in the treatment of certain disorders. It is expected that the compounds of the invention will find application in the treatment of conditions such as non-insulin dependent type 2 diabetes mellitus (NIDDM), insulin resistance, obesity, impaired fasting glucose, impaired glucose tolerance, lipid disorders such as dyslipidemia, hypertension and as well as other diseases and conditions.

CYCLIC AMIDE DERIVATIVES AS INHIBITORS OF 11 - BETA - HYDROXYSTEROID DEHYDROGENASE AND USES THEREOF

The present invention relates to certain amide derivatives that have the ability to inhibit 11-β-hydroxysteroid dehydrogenase type 1 (11β-HSD-1) and which are therefore useful in the treatment of certain disorders that can be prevented or treated by inhibition of this enzyme. In addition the invention relates to the compounds, methods for their preparation, pharmaceutical compositions containing the compounds and the uses of these compounds in the treatment of certain disorders. It is expected that the compounds of the invention will find application in the treatment of conditions such as non-insulin dependent type 2 diabetes mellitus (NIDDM), insulin resistance, obesity, impaired fasting glucose, impaired glucose tolerance, lipid disorders such as dyslipidemia, hypertension and as well as other diseases and conditions.

Indolyl and dihydroindolyl N-glycinamides as potent and in vivo active NPY5 antagonists

A novel series of indolyl and dihydroindolyl glycinamides were identified as potent NPY5 antagonists with in vivo activity from screen hit 1. The dihydroindolyl glycinamide 10a significantly inhibits NPY5 agonist induced feeding at a dose of 0.1 mg/kg. The indolyl glycinamide 12c also inhibits NPY5 agonist induced feeding at a dose of 1 mg/kg. Both compounds 10a and 12c represent potential tools for further investigation into the biology of the NPY5 receptor.

4-AMINOMETHYL-1-ARYL-CYCLOHEXYLAMINE DERIVATIVES

The invention concerns 4-aminomethyl-1-aryl-cyclohexylamine derivatives, methods for producing same, medicines containing said compounds and the use of 4-aminomethyl-1-aryl-cyclohexylamine derivatives for producing medicines.

New N-pyridinyl(methyl)-indolalkanamides acting as topical inflammation inhibitors

The authors have described the synthetic way to new N-pyridinyl(methyl) indolylpropanamides acting as non acidic NSAIDs. Pharmacomodulation was carried out at N-1 and C-5 of the indole ring and at the level of the propanamide chain. N-(pyridin-3-ylmethyl)-3-[5-chloro-1-(4-chlorobenzyl)-indol-3-yl]propanamide 32 represents one of the most potent compounds evaluated in the TPA-induced mouse ear swelling assay, with a level of activity higher than that of ibuprofen and comparable to that of dexamethasone.

Palladium-Assisted N-Alkylation of Indoles: Attempted Application to Polycyclization

The palladium(II) complexes of the olefins ethene, propene, and 1-hexene reacted with 1-lithioindole to produce N-alkylated indoles exclusively.Attempts to perform this N-alkylation intramoleculary (to form tricyclic material from 2-allylskatole) failed.Anilines with dienic side chains in the 2-position were subjected to Pd(II)-assisted cyclization conditions in attempts to induce polycyclization.However, only monocyclization was observed.