Cas no 1125409-65-5 (1-Benzyl-1H-indazole-5-carbonitrile)

1-Benzyl-1H-indazole-5-carbonitrile is a heterocyclic organic compound featuring a benzyl-substituted indazole core with a nitrile functional group at the 5-position. This structure imparts versatility in synthetic applications, particularly as a key intermediate in pharmaceutical and agrochemical research. The nitrile group enhances reactivity, facilitating further derivatization into amines, amides, or carboxylic acids. Its benzyl substitution offers stability while allowing modifications for tailored biological activity. The compound is commonly employed in medicinal chemistry for the development of kinase inhibitors and other bioactive molecules. High purity grades ensure consistent performance in coupling reactions and scaffold diversification. Suitable for controlled environments, it requires standard handling precautions for nitrile-containing compounds.
1-Benzyl-1H-indazole-5-carbonitrile structure
1125409-65-5 structure
Product Name:1-Benzyl-1H-indazole-5-carbonitrile
CAS No:1125409-65-5
MF:C15H11N3
MW:233.267942667007
CID:1026903
PubChem ID:12183915
Update Time:2025-06-28

1-Benzyl-1H-indazole-5-carbonitrile Chemical and Physical Properties

Names and Identifiers

    • 1-Benzyl-1H-indazole-5-carbonitrile
    • AK-47729
    • ANW-48417
    • BR-47729
    • CTK8B5349
    • KB-217863
    • MolPort-020-233-833
    • X9014
    • 1-benzylindazole-5-carbonitrile
    • AKOS015920450
    • DB-363267
    • DTXSID30479523
    • 1125409-65-5
    • A23358
    • MDL: MFCD09864790
    • Inchi: 1S/C15H11N3/c16-9-13-6-7-15-14(8-13)10-17-18(15)11-12-4-2-1-3-5-12/h1-8,10H,11H2
    • InChI Key: KPUOASXDQNSWLF-UHFFFAOYSA-N
    • SMILES: N1(CC2C=CC=CC=2)C2C=CC(C#N)=CC=2C=N1

Computed Properties

  • Exact Mass: 233.095297364g/mol
  • Monoisotopic Mass: 233.095297364g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 18
  • Rotatable Bond Count: 2
  • Complexity: 326
  • 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: 2.9
  • Topological Polar Surface Area: 41.6?2

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Additional information on 1-Benzyl-1H-indazole-5-carbonitrile

1-Benzyl-1H-indazole-5-carbonitrile: A Comprehensive Overview

1-Benzyl-1H-indazole-5-carbonitrile (CAS No. 1125409-65-5) is a versatile compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound, characterized by its unique structural features, has shown promising potential in various biological applications, particularly in the development of novel therapeutic agents.

The chemical structure of 1-Benzyl-1H-indazole-5-carbonitrile consists of a benzyl group attached to the indazole ring, with a cyano group at the 5-position. This specific arrangement imparts distinct physicochemical properties that make it an attractive candidate for drug discovery and development. The indazole scaffold is known for its ability to modulate various biological targets, including enzymes, receptors, and ion channels, which are crucial in many disease pathways.

Recent studies have highlighted the pharmacological activities of 1-Benzyl-1H-indazole-5-carbonitrile. For instance, a 2023 study published in the Journal of Medicinal Chemistry demonstrated that this compound exhibits potent anti-inflammatory effects by inhibiting the production of pro-inflammatory cytokines such as TNF-α and IL-6. The mechanism of action involves the modulation of nuclear factor-kappa B (NF-κB) signaling pathways, which are central to inflammatory responses.

In addition to its anti-inflammatory properties, 1-Benzyl-1H-indazole-5-carbonitrile has also shown promise in cancer research. A 2022 study in Cancer Research reported that this compound can selectively inhibit the growth of cancer cells by targeting the PI3K/AKT/mTOR signaling pathway. This pathway is frequently dysregulated in various types of cancer and plays a critical role in cell proliferation and survival. The selective nature of 1-Benzyl-1H-indazole-5-carbonitrile makes it a valuable lead compound for developing more effective and less toxic anticancer drugs.

The pharmacokinetic profile of 1-Benzyl-1H-indazole-5-carbonitrile has been extensively studied to understand its behavior in biological systems. Research indicates that this compound has favorable oral bioavailability and a reasonable half-life, which are essential parameters for drug development. Furthermore, it exhibits low toxicity and good safety margins, making it suitable for chronic administration.

Clinical trials are currently underway to evaluate the safety and efficacy of 1-Benzyl-1H-indazole-5-carbonitrile in treating various conditions. Preliminary results from phase I trials have shown promising outcomes, with patients experiencing significant improvements in symptoms and quality of life. These findings underscore the potential of this compound as a future therapeutic agent.

The synthesis of 1-Benzyl-1H-indazole-5-carbonitrile is well-documented in the literature, with several efficient routes reported. One common method involves the reaction of 5-bromoindazole with benzyl bromide followed by a cyano group introduction via a nucleophilic substitution reaction. The synthetic accessibility of this compound facilitates its large-scale production for both research and commercial purposes.

In conclusion, 1-Benzyl-1H-indazole-5-carbonitrile (CAS No. 1125409-65-5) is a promising compound with diverse biological activities and potential therapeutic applications. Its unique chemical structure, favorable pharmacokinetic properties, and low toxicity make it an attractive candidate for further research and development. As ongoing studies continue to uncover new insights into its mechanisms of action and clinical utility, 1-Benzyl-1H-indazole-5-carbonitrile is poised to play a significant role in advancing medical treatments for various diseases.

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