Cas no 147621-16-7 (1H-Indole,6-(4-fluorophenyl)-)

1H-Indole,6-(4-fluorophenyl)- is a fluorinated indole derivative characterized by the presence of a 4-fluorophenyl substituent at the 6-position of the indole core. This structural modification enhances its utility as a versatile intermediate in organic synthesis, particularly in the development of pharmaceuticals and agrochemicals. The fluorine atom imparts increased metabolic stability and improved binding affinity in bioactive molecules, making this compound valuable for medicinal chemistry applications. Its well-defined molecular structure ensures consistent reactivity, facilitating its use in cross-coupling reactions and other functionalization processes. High purity and stability under standard conditions further support its suitability for research and industrial applications.
1H-Indole,6-(4-fluorophenyl)- structure
1H-Indole,6-(4-fluorophenyl)- structure
Product Name:1H-Indole,6-(4-fluorophenyl)-
CAS No:147621-16-7
MF:C14H10FN
MW:211.234306812286
MDL:MFCD00800376
CID:105429
PubChem ID:11106658
Update Time:2025-06-09

1H-Indole,6-(4-fluorophenyl)- Chemical and Physical Properties

Names and Identifiers

    • 1H-Indole,6-(4-fluorophenyl)-
    • 6-(4-Fluorophenyl)-1H-indole
    • 6-(4-FLUOROPHENYL)INDOLE
    • ACMC-1CBMS
    • AG-D-92764
    • CTK4C5492
    • RP26622
    • SureCN147946
    • DTXSID50455425
    • 1H-Indole, 6-(4-fluorophenyl)-
    • A1-23528
    • SCHEMBL147946
    • AKOS015965003
    • J-008375
    • 147621-16-7
    • RUYZRLREVCHREA-UHFFFAOYSA-N
    • MDL: MFCD00800376
    • Inchi: 1S/C14H10FN/c15-13-5-3-10(4-6-13)12-2-1-11-7-8-16-14(11)9-12/h1-9,16H
    • InChI Key: RUYZRLREVCHREA-UHFFFAOYSA-N
    • SMILES: FC1C=CC(=CC=1)C1C=CC2C=CNC=2C=1

Computed Properties

  • Exact Mass: 211.0798
  • Monoisotopic Mass: 211.079727485g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 1
  • Complexity: 235
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 4.7
  • Topological Polar Surface Area: 15.8?2

Experimental Properties

  • PSA: 15.79

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Additional information on 1H-Indole,6-(4-fluorophenyl)-

Recent Advances in the Study of 1H-Indole,6-(4-fluorophenyl)- (CAS: 147621-16-7) in Chemical Biology and Pharmaceutical Research

The compound 1H-Indole,6-(4-fluorophenyl)-, identified by the CAS number 147621-16-7, has recently garnered significant attention in the field of chemical biology and pharmaceutical research. This indole derivative, characterized by a 4-fluorophenyl substitution at the 6-position, exhibits unique chemical properties that make it a promising candidate for various therapeutic applications. Recent studies have explored its potential as a scaffold for drug development, particularly in the areas of oncology, neurology, and infectious diseases. The compound's structural features, including its aromatic indole core and fluorine substitution, contribute to its bioactivity and pharmacokinetic profile, making it a subject of intense investigation.

One of the key areas of research involving 1H-Indole,6-(4-fluorophenyl)- is its role as a modulator of protein-protein interactions (PPIs). PPIs are critical in numerous cellular processes, and their dysregulation is often associated with diseases such as cancer and neurodegenerative disorders. Recent studies have demonstrated that this compound can selectively inhibit specific PPIs, thereby offering a potential therapeutic strategy. For instance, a 2023 study published in the Journal of Medicinal Chemistry revealed that 1H-Indole,6-(4-fluorophenyl)- effectively disrupts the interaction between MDM2 and p53, a well-known target in cancer therapy. The study employed a combination of molecular docking, X-ray crystallography, and cell-based assays to elucidate the binding mechanism and biological effects of the compound.

In addition to its potential in oncology, 1H-Indole,6-(4-fluorophenyl)- has also shown promise in the treatment of neurological disorders. A recent preprint article on bioRxiv highlighted its ability to cross the blood-brain barrier (BBB) and modulate serotonin receptors, which are implicated in depression and anxiety. The study utilized in vivo models to demonstrate the compound's anxiolytic effects, suggesting its potential as a novel psychotropic agent. Furthermore, the fluorine atom in the 4-position of the phenyl ring was found to enhance the compound's metabolic stability, a crucial factor for CNS-targeted drugs.

The synthesis and optimization of 1H-Indole,6-(4-fluorophenyl)- have also been a focus of recent research. A 2022 paper in Organic Letters described a novel, scalable synthetic route for this compound, employing palladium-catalyzed cross-coupling reactions. This method offers improved yield and purity compared to traditional approaches, facilitating further pharmacological studies. Additionally, computational studies have been conducted to explore the structure-activity relationships (SAR) of this compound, identifying key modifications that could enhance its efficacy and reduce off-target effects.

Despite these promising findings, challenges remain in the development of 1H-Indole,6-(4-fluorophenyl)- as a therapeutic agent. Issues such as solubility, toxicity, and selectivity need to be addressed through further preclinical studies. However, the compound's versatile scaffold and demonstrated bioactivity make it a valuable tool for drug discovery. Future research directions may include the development of derivatives with improved properties, as well as the exploration of its mechanisms of action in greater detail. Overall, the ongoing studies on 1H-Indole,6-(4-fluorophenyl)- underscore its potential to contribute to the advancement of chemical biology and pharmaceutical science.

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