Production Method 1

281204-54-4

951626-33-8

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane ,  Water ;  1 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  acidified, 0 °C

Reference

Structure-activity relationship analysis of the peptide deformylase inhibitor 5-bromo-1H-indole-3-acetohydroxamic acid

Petit, Sylvain; Duroc, Yann; Larue, Valery; Giglione, Carmela; Leon, Carole; et al, ChemMedChem, 2009, 4(2), 261-275

Production Method 2

105-36-2

52415-29-9

951626-33-8

Reaction Conditions

1.1 Reagents: Potassium carbonate ,  Potassium iodide Solvents: Acetonitrile ;  20 min, 160 °C
1.2 Solvents: Diethyl ether ,  Water ;  rt
1.3 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane ,  Water ;  3 h, 25 °C
1.4 Reagents: Hydrochloric acid Solvents: Water ;  acidified, 25 °C

Reference

Total Synthesis and Biological Evaluation of Phidianidines A and B Uncovers Unique Pharmacological Profiles at CNS Targets

Brogan, John T.; Stoops, Sydney L.; Lindsley, Craig W., ACS Chemical Neuroscience, 2012, 3(9), 658-664

2-(6-Bromo-1H-indol-1-yl)acetic Acid Raw materials

• Ethyl bromoacetate
• 6-Bromoindole
• ethyl 2-(6-bromo-1H-indol-1-yl)acetate

2-(6-Bromo-1H-indol-1-yl)acetic Acid Preparation Products

• 2-(6-Bromo-1H-indol-1-yl)acetic Acid (951626-33-8)

• 1. Emerging investigator series: first-principles and thermodynamics comparison of compositionally-tuned delafossites: cation release from the (001) surface of complex metal oxides?
  Joseph W. Bennett,Diamond T. Jones,Blake G. Hudson,Joshua Melendez-Rivera,Robert J. Hamers,Sara E. Mason Environ. Sci.: Nano, 2020,7, 1642-1651
• 2. Emergence of microfluidic wearable technologies
  Joo Chuan Yeo,Kenry Lab Chip, 2016,16, 4082-4090
• 3. Evolutionary approaches in protein engineering towards biomaterial construction
  Brindha J.,Balamurali M. M.,Kaushik Chanda RSC Adv., 2019,9, 34720-34734
• 4. Evolutionary de novo design of phenothiazine derivatives for dye-sensitized solar cells?
  Vishwesh Venkatraman,Marco Foscato,Vidar R. Jensen,Bj?rn K?re Alsberg J. Mater. Chem. A, 2015,3, 9851-9860
• 5. Fe/Fe3C@C nanoparticles encapsulated in N-doped graphene–CNTs framework as an efficient bifunctional oxygen electrocatalyst for robust rechargeable Zn–air batteries?
  Zhiyan Chen,Nan Wu,Yaobing Wang,Bing Wang,Yingde Wang J. Mater. Chem. A, 2018,6, 516-526

Introduction to 2-(6-Bromo-1H-indol-1-yl)acetic Acid (CAS No. 951626-33-8) and Its Emerging Applications in Chemical Biology

2-(6-Bromo-1H-indol-1-yl)acetic acid, identified by the CAS number 951626-33-8, is a significant compound in the realm of chemical biology and pharmaceutical research. This molecule, featuring a brominated indole core linked to an acetic acid moiety, has garnered considerable attention due to its structural versatility and potential biological activities. The indole scaffold, a well-documented pharmacophore, is renowned for its role in modulating various biological pathways, while the bromine substituent enhances its reactivity, making it a valuable intermediate in synthetic chemistry.

The compound's unique structural features position it as a promising candidate for drug discovery and therapeutic development. Recent studies have highlighted its utility in the synthesis of novel bioactive molecules, particularly in the context of targeting inflammatory and neurodegenerative diseases. The acetic acid side chain not only contributes to the molecule's solubility but also provides a handle for further functionalization, enabling the creation of derivatives with tailored properties.

One of the most compelling aspects of 2-(6-Bromo-1H-indol-1-yl)acetic acid is its role as a key intermediate in the synthesis of indole-based inhibitors. These inhibitors have shown promise in preclinical studies for their ability to modulate enzymes involved in critical cellular processes. For instance, derivatives of this compound have been investigated for their potential to inhibit cyclooxygenase (COX) enzymes, which are central players in the inflammatory response. By targeting COX enzymes, these derivatives may offer therapeutic benefits similar to nonsteroidal anti-inflammatory drugs (NSAIDs) but with potentially improved selectivity and reduced side effects.

Furthermore, the brominated indole moiety in 2-(6-Bromo-1H-indol-1-yl)acetic acid makes it an attractive building block for exploring structure-activity relationships (SAR). Researchers have leveraged this reactivity to develop libraries of indole derivatives for high-throughput screening (HTS). Such screens have identified compounds with potent activity against various disease targets, including kinases and transcription factors. The bromine atom's presence allows for further chemical modifications via cross-coupling reactions, such as Suzuki-Miyaura or Buchwald-Hartwig couplings, which are essential for constructing complex molecular architectures.

In the field of oncology, 2-(6-Bromo-1H-indol-1-yl)acetic acid has been explored as a precursor for developing small-molecule inhibitors of tyrosine kinases. These kinases are aberrantly activated in many cancers and play a crucial role in tumor growth and progression. By designing molecules that specifically inhibit these kinases, researchers aim to develop targeted therapies that minimize systemic toxicity. Preliminary studies suggest that certain derivatives of this compound exhibit inhibitory activity against mutant forms of kinases associated with resistance to current treatments.

The compound's potential extends beyond its role as an intermediate; it also serves as a scaffold for developing probes to study protein-protein interactions. The indole ring can be coupled with fluorophores or other reporter groups, enabling researchers to visualize and quantify interactions in living cells. This approach has been instrumental in understanding complex signaling networks and identifying novel therapeutic targets.

Recent advances in computational chemistry have further enhanced the utility of 2-(6-Bromo-1H-indol-1-yl)acetic acid. Molecular modeling studies have predicted new derivatives with enhanced binding affinity and selectivity for target proteins. These predictions are validated through experimental synthesis and characterization, leading to iterative improvements in molecular design. Such interdisciplinary approaches highlight the importance of integrating computational tools with traditional synthetic methods to accelerate drug discovery.

The growing interest in 2-(6-Bromo-1H-indol-1-yl)acetic acid is also driven by its compatibility with green chemistry principles. Researchers are increasingly focused on developing synthetic routes that minimize waste and hazardous byproducts. The use of this compound as an intermediate allows for the construction of complex molecules through efficient and sustainable methodologies. For example, catalytic processes that employ palladium or nickel catalysts have been optimized for generating indole derivatives while maintaining high yields and selectivity.

In conclusion, 2-(6-Bromo-1H-indol-1-yl)acetic acid (CAS No. 951626-33-8) represents a versatile and promising compound in chemical biology and pharmaceutical research. Its unique structural features make it an invaluable tool for developing novel bioactive molecules targeting various diseases. As research continues to uncover new applications and synthetic strategies, this compound is poised to play an increasingly significant role in advancing therapeutic innovation.

• 24297-59-4(2-(1H-indol-1-yl)acetic acid)
• 1094351-56-0(Methyl 2-(5-bromo-1H-indol-1-yl)acetate)
• 903499-26-3(4-Bromo-1-(2-methoxyethyl)-1H-Indole)
• 726174-45-4((5-Bromo-1H-indol-1-YL)-acetic acid ethyl ester)
• 124985-06-4(Ethyl 2-(3,6-dibromo-9H-carbazol-9-yl)acetate)
• 281204-55-5(1H-Indole-1-ethanol, 6-bromo-)
• 148366-28-3(2-(5-bromo-1H-indol-1-yl)ethan-1-ol)
• 524-80-1(2-(9H-Carbazol-9-yl)acetic acid)
• 651056-45-0(1H-Indole-1-acetic acid, 6-bromo-, methyl ester)
• 56950-15-3(Quinolinium, 1-(carboxymethyl)-, bromide)