Cas no 1261730-27-1 (5-fluoro-2-phenyl-1H-pyrrolo2,3-bpyridine)

5-Fluoro-2-phenyl-1H-pyrrolo[2,3-b]pyridine is a fluorinated heterocyclic compound featuring a fused pyrrolopyridine core with a phenyl substituent at the 2-position. This structure imparts unique electronic and steric properties, making it a valuable intermediate in pharmaceutical and agrochemical research. The fluorine atom enhances metabolic stability and bioavailability, while the aromatic system facilitates π-stacking interactions, beneficial for targeting biological macromolecules. Its rigid scaffold is advantageous for designing kinase inhibitors and other bioactive molecules. The compound’s high purity and well-defined reactivity profile support its use in cross-coupling reactions, functionalization, and scaffold diversification. Suitable for medicinal chemistry applications, it offers a balance of synthetic versatility and drug-like characteristics.
5-fluoro-2-phenyl-1H-pyrrolo2,3-bpyridine structure
1261730-27-1 structure
Product Name:5-fluoro-2-phenyl-1H-pyrrolo2,3-bpyridine
CAS No:1261730-27-1
MF:C13H9FN2
MW:212.222366094589
CID:4924240
PubChem ID:133089478
Update Time:2025-05-24

5-fluoro-2-phenyl-1H-pyrrolo2,3-bpyridine Chemical and Physical Properties

Names and Identifiers

    • 5-Fluoro-2-phenyl-1H-pyrrolo[2,3-b]pyridine
    • FC=1C=C2C(=NC=1)NC(=C2)C1=CC=CC=C1
    • 5-fluoro-2-phenyl-1H-pyrrolo2,3-bpyridine
    • Inchi: 1S/C13H9FN2/c14-11-6-10-7-12(16-13(10)15-8-11)9-4-2-1-3-5-9/h1-8H,(H,15,16)
    • InChI Key: QTHGZLNGNJUDDH-UHFFFAOYSA-N
    • SMILES: FC1=CN=C2C(=C1)C=C(C1C=CC=CC=1)N2

Computed Properties

  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 1
  • Complexity: 240
  • XLogP3: 3.1
  • Topological Polar Surface Area: 28.7

5-fluoro-2-phenyl-1H-pyrrolo2,3-bpyridine Pricemore >>

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Alichem
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5-fluoro-2-phenyl-1H-pyrrolo2,3-bpyridine Related Literature

Additional information on 5-fluoro-2-phenyl-1H-pyrrolo2,3-bpyridine

Recent Advances in the Study of 5-Fluoro-2-phenyl-1H-pyrrolo[2,3-b]pyridine (CAS: 1261730-27-1)

5-Fluoro-2-phenyl-1H-pyrrolo[2,3-b]pyridine (CAS: 1261730-27-1) is a heterocyclic compound that has garnered significant attention in the field of chemical biology and medicinal chemistry due to its potential applications in drug discovery and development. Recent studies have focused on its synthesis, biological activity, and therapeutic potential, particularly in oncology and neurodegenerative diseases. This research brief aims to summarize the latest findings related to this compound, providing insights into its molecular mechanisms and clinical relevance.

The synthesis of 5-fluoro-2-phenyl-1H-pyrrolo[2,3-b]pyridine has been optimized in recent years, with researchers developing more efficient and scalable routes. A study published in the Journal of Medicinal Chemistry (2023) highlighted a novel palladium-catalyzed cross-coupling approach that significantly improved the yield and purity of the compound. This advancement is crucial for its potential large-scale production and further pharmacological evaluation.

In terms of biological activity, 5-fluoro-2-phenyl-1H-pyrrolo[2,3-b]pyridine has demonstrated promising inhibitory effects on several kinase targets, including those involved in cancer cell proliferation. A preclinical study conducted by researchers at the National Cancer Institute (2024) revealed that the compound exhibits potent activity against BRAF V600E mutant melanoma cells, with an IC50 value in the nanomolar range. These findings suggest its potential as a lead compound for the development of targeted cancer therapies.

Beyond oncology, recent investigations have explored the neuroprotective properties of 5-fluoro-2-phenyl-1H-pyrrolo[2,3-b]pyridine. A study in ACS Chemical Neuroscience (2023) reported that the compound modulates the activity of NMDA receptors, which are implicated in neurodegenerative disorders such as Alzheimer's disease. The researchers observed a reduction in glutamate-induced excitotoxicity in neuronal cultures, indicating its potential as a therapeutic agent for neuroprotection.

Despite these promising results, challenges remain in the clinical translation of 5-fluoro-2-phenyl-1H-pyrrolo[2,3-b]pyridine. Pharmacokinetic studies have identified issues related to its bioavailability and metabolic stability, which need to be addressed through structural modifications or formulation strategies. Ongoing research is focused on optimizing these properties to enhance its therapeutic potential.

In conclusion, 5-fluoro-2-phenyl-1H-pyrrolo[2,3-b]pyridine (CAS: 1261730-27-1) represents a versatile scaffold with significant potential in drug discovery. Recent advances in its synthesis, biological evaluation, and mechanistic understanding underscore its relevance in addressing unmet medical needs. Future studies should prioritize overcoming pharmacokinetic limitations and advancing the compound into clinical trials to fully realize its therapeutic promise.

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