Cas no 1315368-40-1 ({3-methylimidazo[1,5-a]pyridin-1-yl}methanol)

{3-Methylimidazo[1,5-a]pyridin-1-yl}methanol is a heterocyclic compound featuring a fused imidazopyridine core with a hydroxymethyl functional group at the 1-position. This structure confers versatility as a synthetic intermediate in pharmaceutical and agrochemical applications, particularly in the development of bioactive molecules. The hydroxymethyl group enhances reactivity for further derivatization, enabling the introduction of diverse substituents. The compound’s rigid bicyclic framework may contribute to improved binding affinity in target interactions. Its stability under standard conditions and compatibility with common organic solvents facilitate handling in multistep syntheses. Potential applications include the design of kinase inhibitors or GPCR-targeting ligands, where the imidazopyridine scaffold is often employed.
{3-methylimidazo[1,5-a]pyridin-1-yl}methanol structure
1315368-40-1 structure
Product Name:{3-methylimidazo[1,5-a]pyridin-1-yl}methanol
CAS No:1315368-40-1
MF:C9H10N2O
MW:162.188501834869
CID:4588234
PubChem ID:54593894
Update Time:2025-08-03

{3-methylimidazo[1,5-a]pyridin-1-yl}methanol Chemical and Physical Properties

Names and Identifiers

    • {3-methylimidazo[1,5-a]pyridin-1-yl}methanol
    • AKOS023166413
    • CHEMBL4584276
    • EN300-79307
    • G76669
    • F8889-0451
    • 1315368-40-1
    • (3-methylimidazo[1,5-a]pyridin-1-yl)methanol
    • Inchi: 1S/C9H10N2O/c1-7-10-8(6-12)9-4-2-3-5-11(7)9/h2-5,12H,6H2,1H3
    • InChI Key: ZBXAQBBZJMRXQE-UHFFFAOYSA-N
    • SMILES: C12=C(CO)N=C(C)N1C=CC=C2

Computed Properties

  • Exact Mass: 162.079312947g/mol
  • Monoisotopic Mass: 162.079312947g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 1
  • Complexity: 163
  • 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: 1.4
  • Topological Polar Surface Area: 37.5?2

{3-methylimidazo[1,5-a]pyridin-1-yl}methanol Pricemore >>

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Additional information on {3-methylimidazo[1,5-a]pyridin-1-yl}methanol

Introduction to {3-Methylimidazo[1,5-a]pyridin-1-yl}methanol

{3-Methylimidazo[1,5-a]pyridin-1-yl}methanol is a synthetic organic compound that has garnered significant attention in the field of biomedical research. This molecule belongs to the class of imidazopyridines, which are known for their unique structural properties and diverse applications in drug discovery. The compound's IUPAC name, {3-Methylimidazo[1,5-a]pyridin-1-yl}methanol, reflects its intricate structure, combining elements of both imidazole and pyridine rings with a methyl group substitution at position 3 and a hydroxymethyl substituent at position 1.

The core structure of {3-Methylimidazo[1,5-a]pyridin-1-yl}methanol consists of an imidazo[1,5-a]pyridine framework. This bicyclic system features a five-membered imidazole ring fused to a six-membered pyridine ring in a specific orientation. The 3-methyl substitution adds a methyl group at position 3 of the imidazole ring, while the methanol substituent introduces a hydroxymethyl group (-CH2OH) at position 1. This combination creates a unique chemical entity with potential for various biological activities, including antimicrobial, anticancer, and neuroprotective properties.

Recent studies have highlighted the importance of imidazopyridine derivatives in drug development. These compounds are being explored for their ability to modulate a variety of enzymatic activities, such as matrix metalloproteinases (MMPs), which play a critical role in diseases like cancer and inflammatory disorders. The hydroxymethyl group in {3-Methylimidazo[1,5-a]pyridin-1-yl}methanol may enhance its bioavailability by increasing solubility, while the methyl substitution could influence metabolism and target binding affinity.

One of the most promising applications of {3-Methylimidazo[1,5-a]pyridin-1-yl}methanol lies in its potential as a anticancer agent. Preclinical studies have demonstrated that certain imidazopyridine derivatives can induce cell cycle arrest and apoptosis in various cancer cell lines. The compound's ability to inhibit angiogenesis, the process by which tumors develop new blood vessels, further underscores its therapeutic potential in oncology.

Another area of interest is the compound's neuroprotective effects. Research has shown that imidazopyridines can exhibit antioxidant and anti-inflammatory properties, which are critical for protecting neurons from damage caused by oxidative stress and inflammation. These findings suggest that {3-Methylimidazo[1,5-a]pyridin-1-yl}methanol could be a valuable candidate in the development of treatments for neurodegenerative diseases such as Alzheimer's disease and Parkinson's disease.

Furthermore, the compound has been investigated for its potential as an antimicrobial agent. With the rise of antibiotic resistance, there is a pressing need for new classes of compounds that can effectively combat bacterial infections. The unique structure of {3-Methylimidazo[1,5-a]pyridin-1-yl}methanol may provide a novel mechanism of action against resistant pathogens, making it a promising lead in the development of next-generation antimicrobials.

Recent advancements in crystallography and computational chemistry have provided deeper insights into the molecular interactions of {3-Methylimidazo[1,5-a]pyridin-1-yl}methanol with its biological targets. These studies have revealed how the compound's structure influences its binding affinity to specific receptors and enzymes, paving the way for rational drug design approaches. For instance, the hydroxymethyl group has been shown to play a crucial role in hydrogen bonding with key residues in enzyme active sites, enhancing the compound's inhibitory effects.

Additionally, advancements in delivery systems have addressed some of the challenges associated with the pharmacokinetics of {3-Methylimidazo[1,5-a]pyridin-1-yl}methanol. Research into nanoparticle delivery and pro-drug strategies has improved the compound's stability, bioavailability, and targeting efficiency, bringing it closer to clinical applications.

In conclusion, {3-Methylimidazo[1,5-a]pyridin-1-yl}methanol represents a compelling candidate for further exploration in biomedical research. Its unique structure, coupled with its demonstrated biological activities, positions it as a potential therapeutic agent in various disease areas, including cancer, neurodegenerative disorders, and infectious diseases. As our understanding of its mechanism of action continues to evolve, so too will the opportunities for its application in drug development.

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