Cas no 2654-13-9 (2-(phenylmethyl)-3H-Imidazo[4,5-c]pyridine)

2-(Phenylmethyl)-3H-Imidazo[4,5-c]pyridine is a heterocyclic compound featuring an imidazopyridine core with a benzyl substituent. This structure imparts unique electronic and steric properties, making it a valuable intermediate in pharmaceutical and agrochemical research. Its fused ring system enhances stability and offers versatile reactivity for further functionalization. The compound is particularly useful in the synthesis of bioactive molecules, including potential kinase inhibitors and antimicrobial agents. Its well-defined crystalline form ensures consistent purity and handling characteristics. Suitable for controlled reactions, it serves as a key building block in medicinal chemistry, enabling the development of targeted therapeutics with improved efficacy and selectivity.
2-(phenylmethyl)-3H-Imidazo[4,5-c]pyridine structure
2654-13-9 structure
Product Name:2-(phenylmethyl)-3H-Imidazo[4,5-c]pyridine
CAS No:2654-13-9
MF:C13H11N3
MW:209.246542215347
CID:843239
PubChem ID:63268638
Update Time:2025-06-09

2-(phenylmethyl)-3H-Imidazo[4,5-c]pyridine Chemical and Physical Properties

Names and Identifiers

    • 2-(phenylmethyl)-3H-Imidazo[4,5-c]pyridine
    • 2-benzyl-3H-imidazo[4,5-c]pyridine
    • 3H-Imidazo[4,5-c]pyridine, 2-(phenylmethyl)-
    • 2654-13-9
    • AKOS012572129
    • DB-338108
    • DTXSID20734557
    • MDL: MFCD18305787
    • Inchi: 1S/C13H11N3/c1-2-4-10(5-3-1)8-13-15-11-6-7-14-9-12(11)16-13/h1-7,9H,8H2,(H,15,16)
    • InChI Key: HRQRBCRHCRDWMJ-UHFFFAOYSA-N
    • SMILES: N1C2C=NC=CC=2N=C1CC1C=CC=CC=1

Computed Properties

  • Exact Mass: 209.095297364g/mol
  • Monoisotopic Mass: 209.095297364g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 2
  • Complexity: 225
  • 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: 2.4
  • Topological Polar Surface Area: 41.6?2

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Additional information on 2-(phenylmethyl)-3H-Imidazo[4,5-c]pyridine

Professional Introduction to 2-(phenylmethyl)-3H-Imidazo[4,5-c]pyridine (CAS No. 2654-13-9)

2-(phenylmethyl)-3H-Imidazo[4,5-c]pyridine, identified by its Chemical Abstracts Service (CAS) number 2654-13-9, is a heterocyclic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal biology. This compound belongs to the imidazopyridine class, a structural motif known for its broad spectrum of biological activities and potential therapeutic applications. The presence of a phenylmethyl (benzyl) group and the fused imidazo[4,5-c]pyridine ring system imparts unique electronic and steric properties, making it a versatile scaffold for drug discovery and development.

The imidazopyridine scaffold has been extensively studied due to its ability to interact with various biological targets, including enzymes and receptors. Recent advancements in structure-activity relationship (SAR) studies have highlighted the importance of optimizing the substitution patterns on the imidazopyridine core to enhance binding affinity and selectivity. Specifically, 2-(phenylmethyl)-3H-Imidazo[4,5-c]pyridine has been investigated for its potential as an inhibitor of kinases and other enzymes involved in cancer progression. The benzyl group at the 2-position contributes to solubility and metabolic stability, while the imidazopyridine ring system provides a privileged structure for molecular recognition.

In the realm of oncology research, 2-(phenylmethyl)-3H-Imidazo[4,5-c]pyridine has been explored as a lead compound for developing novel anticancer agents. Preclinical studies have demonstrated its ability to disrupt signaling pathways critical for tumor growth and survival. For instance, it has shown promise in inhibiting tyrosine kinases, which are often overexpressed in various cancers. The compound's mechanism of action involves binding to the ATP-binding site of these kinases, thereby preventing substrate phosphorylation and downstream signaling. This mode of action aligns with the growing interest in kinase inhibitors as targeted therapies.

Furthermore, the structural features of 2-(phenylmethyl)-3H-Imidazo[4,5-c]pyridine make it an attractive candidate for further derivatization to improve pharmacokinetic properties and reduce off-target effects. Researchers have employed computational methods such as molecular docking and virtual screening to identify analogs with enhanced potency and selectivity. These efforts have led to the identification of several novel derivatives that exhibit superior biological activity in vitro and in vivo. The benzyl group serves as a key pharmacophore, contributing to both binding affinity and solubility, while modifications at other positions can fine-tune metabolic stability and bioavailability.

The synthesis of 2-(phenylmethyl)-3H-Imidazo[4,5-c]pyridine involves multi-step organic reactions that highlight the synthetic versatility of heterocyclic chemistry. Common synthetic routes include condensation reactions between appropriate precursors followed by functional group transformations. Advances in synthetic methodologies have enabled more efficient and scalable production processes, making it feasible to conduct large-scale screening studies for drug discovery applications. The availability of high-quality starting materials and robust synthetic protocols has facilitated rapid progress in exploring the therapeutic potential of this compound.

Recent publications have highlighted the role of 2-(phenylmethyl)-3H-Imidazo[4,5-c]pyridine in addressing unmet medical needs by targeting specific disease pathways. For example, studies have shown its efficacy in preclinical models of chronic inflammatory diseases by modulating immune cell function. The compound's ability to interact with intracellular signaling cascades suggests its potential as an immunomodulatory agent. Additionally, its structural similarity to known bioactive molecules has prompted investigations into its role in neurodegenerative disorders, where dysregulation of kinase activity is implicated.

The pharmacological profile of 2-(phenylmethyl)-3H-Imidazo[4,5-c]pyridine is further enhanced by its favorable pharmacokinetic properties. Studies indicate that it exhibits good oral bioavailability and moderate tissue distribution, which are critical factors for therapeutic efficacy. Metabolic stability studies have revealed that the benzyl group contributes to resistance against enzymatic degradation by cytochrome P450 enzymes. This characteristic is particularly advantageous for developing long-acting drugs that require fewer dosing regimens.

In conclusion,2-(phenylmethyl)-3H-Imidazo[4,5-c]pyridine (CAS No. 2654-13-9) represents a promising scaffold for pharmaceutical innovation with significant potential in oncology and other therapeutic areas. Its unique structural features enable interactions with key biological targets, while its synthetic accessibility supports rapid development of novel derivatives. Ongoing research continues to uncover new applications for this compound, underscoring its importance in modern drug discovery efforts.

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