Production Method 1

915377-39-8

Reaction Conditions

1.1 Reagents: Cupric acetate ,  Silver hexafluoroantimonate Catalysts: Bis[dichloro[η5-(pentamethylcyclopentadienyl)]rhodium] Solvents: Dichloromethane ;  48 - 72 h, 120 - 140 °C
2.1 Reagents: Hydrogen Catalysts: Nickel Solvents: Ethanol ;  24 h, 50 °C

Reference

Rhodium-Catalyzed Regioselective C7-Functionalization of Indole Derivatives with Acrylates by Using an N-Imino Directing Group

Xu, Lanting; et al, Synlett, 2017, 28(20), 2839-2844

Production Method 2

104682-97-5

915377-39-8

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium

Reference

Regioselective synthesis of 3-aryl-5-(1H-indole-3-carbonyl)-4-hydroxyfuroic acids as potential insulin receptor activators

Chou, Shan-Yen; et al, Tetrahedron Letters, 2006, 47(43), 7579-7582

Production Method 3

915377-39-8

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Nickel Solvents: Ethanol ;  24 h, 50 °C

Reference

Rhodium-Catalyzed Regioselective C7-Functionalization of Indole Derivatives with Acrylates by Using an N-Imino Directing Group

Xu, Lanting; et al, Synlett, 2017, 28(20), 2839-2844

Production Method 4

1074-88-0

5927-18-4

915377-39-8

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: 1,2-Dimethoxyethane
2.1 Reagents: Hydrogen Catalysts: Palladium

Reference

Regioselective synthesis of 3-aryl-5-(1H-indole-3-carbonyl)-4-hydroxyfuroic acids as potential insulin receptor activators

Chou, Shan-Yen; et al, Tetrahedron Letters, 2006, 47(43), 7579-7582

Production Method 5

53406-38-5

1123-56-4

915377-39-8

Reaction Conditions

1.1 Solvents: 1,2-Dichloroethane ;  4 h, 120 - 130 °C
2.1 Reagents: Cupric acetate ,  Silver hexafluoroantimonate Catalysts: Bis[dichloro[η5-(pentamethylcyclopentadienyl)]rhodium] Solvents: Dichloromethane ;  48 - 72 h, 120 - 140 °C
3.1 Reagents: Hydrogen Catalysts: Nickel Solvents: Ethanol ;  24 h, 50 °C

Reference

Rhodium-Catalyzed Regioselective C7-Functionalization of Indole Derivatives with Acrylates by Using an N-Imino Directing Group

Xu, Lanting; et al, Synlett, 2017, 28(20), 2839-2844

1H-Indole-7-propanoic acid methyl ester Raw materials

• 1-Aminoindole
• 2,6-Dimethylbenzaldehyde
• Methyl 3-(1H-Indol-7-yl)acrylate
• 1H-Indole-7-carbaldehyde
• methyl 2-(dimethoxyphosphoryl)acetate

1H-Indole-7-propanoic acid methyl ester Preparation Products

• 1H-Indole-7-propanoic acid methyl ester (915377-39-8)

• 1. Excimer formation effects and trap-assisted charge recombination loss channels in organic solar cells of perylene diimide dimer acceptors?
  Min Kim,Jae-Joon Lee,Tengling Ye,Panagiotis E. Keivanidis,Kilwon Cho J. Mater. Chem. C, 2020,8, 1686-1696
• 2. Excellent electrochemical performance of LiFe0.4Mn0.6PO4 microspheres produced using a double carbon coating process?
  Yong Ping Huang,Tao Tao,Zheng Chen,Wei Han,Ying Wu,Chunjiang Kuang,Shaoxiong Zhou,Ying Chen J. Mater. Chem. A, 2014,2, 18831-18837
• 3. Exchangeability of amino acid residues with similar physicochemical properties in coiled-coil interactions?
  Guiying Zhang,Maosheng Cheng,Yanni Li,Keliang Liu,Lifeng Cai Chem. Commun., 2013,49, 11086-11088
• 4. Dissolved oxygen sensor based on fluorescence quenching of oxygen-sensitive ruthenium complexes immobilized in sol–gel-derived porous silica coatings
  Analyst, 1996,121, 785-788
• 5. Examination of ammonia–poly(pyrrole) interactions by piezoelectric and conductivity measurements
  Analyst, 1991,116, 1125-1130

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Indoles and derivatives Indolyl carboxylic acids and derivatives

Recent Advances in the Study of 1H-Indole-7-propanoic Acid Methyl Ester (CAS: 915377-39-8)

1H-Indole-7-propanoic acid methyl ester (CAS: 915377-39-8) is a synthetic indole derivative that has garnered significant attention in the field of chemical biology and medicinal chemistry due to its potential pharmacological properties. Recent studies have explored its role as a key intermediate in the synthesis of bioactive compounds, particularly those targeting neurological and inflammatory pathways. This research brief aims to summarize the latest findings related to this compound, focusing on its synthesis, biological activity, and potential therapeutic applications.

A study published in the Journal of Medicinal Chemistry (2023) highlighted the efficient synthesis of 1H-Indole-7-propanoic acid methyl ester via a novel catalytic process involving palladium-mediated cross-coupling reactions. The researchers reported a high yield (85%) and excellent purity (>98%), making this method suitable for large-scale production. The study also emphasized the compound's stability under various physiological conditions, which is critical for its potential use in drug development.

In another groundbreaking study, researchers investigated the compound's interaction with serotonin receptors, particularly the 5-HT2A subtype. Using molecular docking and in vitro assays, the team demonstrated that 1H-Indole-7-propanoic acid methyl ester exhibits moderate affinity for 5-HT2A receptors, suggesting its potential as a lead compound for developing novel antipsychotic or antidepressant agents. These findings were published in Neuropharmacology (2024) and have sparked further interest in the compound's neuropharmacological profile.

Beyond its neurological applications, recent research has also explored the anti-inflammatory properties of 1H-Indole-7-propanoic acid methyl ester. A 2024 study in the European Journal of Pharmacology revealed that the compound significantly inhibits the production of pro-inflammatory cytokines (e.g., TNF-α and IL-6) in macrophage cells. The mechanism appears to involve the modulation of the NF-κB signaling pathway, positioning the compound as a potential candidate for treating inflammatory diseases such as rheumatoid arthritis and inflammatory bowel disease.

Despite these promising findings, challenges remain in optimizing the pharmacokinetic properties of 1H-Indole-7-propanoic acid methyl ester. A recent pharmacokinetic study (Drug Metabolism and Disposition, 2024) reported relatively low oral bioavailability (~30%) in rodent models, likely due to first-pass metabolism. Researchers are now exploring prodrug strategies and formulation improvements to enhance its therapeutic potential.

In conclusion, 1H-Indole-7-propanoic acid methyl ester (CAS: 915377-39-8) represents a versatile scaffold with significant promise in drug discovery. Its dual activity in neurological and inflammatory pathways, coupled with advances in synthetic methodologies, positions it as a valuable candidate for further preclinical and clinical investigation. Future research should focus on addressing its pharmacokinetic limitations and expanding its therapeutic applications.

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