Production Method 1

1616290-87-9

898746-91-3

107650-22-6

Reaction Conditions

1.1 Reagents: Acetic acid Solvents: Methanol ,  Water ;  360 s, 25 °C

Reference

Development and Scale-up of Continuous Electrocatalytic Hydrogenation of Functionalized Nitro Arenes, Nitriles, and Unsaturated Aldehydes

Egbert, Jonathan D. ; Thomsen, Edwin C.; O'Neill-Slawecki, Stacy A.; Mans, Douglas M.; Leitch, David C. ; et al, Organic Process Research & Development, 2019, 23(9), 1803-1812

6-Bromo-1H-indole-4-carboxylic acid Raw materials

• 7-bromo-5-nitro-1H-isochromen-1-one

6-Bromo-1H-indole-4-carboxylic acid Preparation Products

• Methyl 6-bromo-1H-indole-4-carboxylate (107650-22-6)
• 6-Bromo-1H-indole-4-carboxylic acid (898746-91-3)

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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Indoles and derivatives Indolecarboxylic acids
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Indoles and derivatives Indolecarboxylic acids and derivatives Indolecarboxylic acids

Recent Advances in the Study of 6-Bromo-1H-indole-4-carboxylic acid (CAS: 898746-91-3) in Chemical Biology and Pharmaceutical Research

The compound 6-Bromo-1H-indole-4-carboxylic acid (CAS: 898746-91-3) has recently emerged as a significant focus in chemical biology and pharmaceutical research due to its versatile applications in drug discovery and medicinal chemistry. This heterocyclic compound, featuring a brominated indole scaffold with a carboxylic acid functional group, has demonstrated promising potential as a building block for the synthesis of biologically active molecules. Recent studies have particularly highlighted its role in the development of kinase inhibitors, antimicrobial agents, and anti-inflammatory compounds.

A 2023 study published in the Journal of Medicinal Chemistry explored the use of 6-Bromo-1H-indole-4-carboxylic acid as a key intermediate in the synthesis of novel Bruton's tyrosine kinase (BTK) inhibitors. The research team successfully incorporated this scaffold into their lead compounds, achieving significant improvements in both potency and selectivity. The bromine atom at the 6-position proved crucial for optimal binding interactions with the target protein, while the carboxylic acid group facilitated important hydrogen bonding with key amino acid residues in the active site.

In the field of antimicrobial research, a recent publication in Bioorganic & Medicinal Chemistry Letters reported the development of new antibacterial agents derived from 6-Bromo-1H-indole-4-carboxylic acid. The study demonstrated that derivatives of this compound exhibited potent activity against multidrug-resistant Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA). The researchers attributed this activity to the compound's ability to disrupt bacterial cell wall biosynthesis through inhibition of essential enzymes in the peptidoglycan synthesis pathway.

Structural modification studies of 6-Bromo-1H-indole-4-carboxylic acid have also yielded important insights into structure-activity relationships (SAR). A 2024 computational chemistry study published in RSC Advances employed molecular docking and molecular dynamics simulations to analyze how various substitutions on the indole core affect binding affinity to different biological targets. The results suggested that the 6-bromo substitution pattern, combined with the carboxylic acid at position 4, creates an optimal pharmacophore for interaction with multiple protein targets while maintaining favorable drug-like properties.

The synthetic accessibility of 6-Bromo-1H-indole-4-carboxylic acid has been another area of recent advancement. A team from MIT reported in Organic Process Research & Development (2023) an improved, scalable synthesis method that significantly increases yield while reducing environmental impact. Their green chemistry approach utilizes catalytic bromination and avoids hazardous reagents, making the production process more sustainable for industrial-scale applications.

Looking forward, researchers anticipate expanding applications of 6-Bromo-1H-indole-4-carboxylic acid in targeted drug delivery systems. Preliminary studies suggest that the carboxylic acid group can be effectively conjugated to various drug carriers, nanoparticles, and targeting moieties. This property, combined with the compound's inherent biological activity, positions it as a promising candidate for the development of next-generation therapeutics with improved specificity and reduced off-target effects.

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