Cas no 1038827-63-2 (6-fluoro-Imidazo[1,2-a]pyridine-2-methanol)

6-Fluoro-Imidazo[1,2-a]pyridine-2-methanol is a fluorinated heterocyclic compound featuring an imidazopyridine core with a hydroxymethyl substituent at the 2-position. The presence of the fluorine atom at the 6-position enhances its electronic properties and potential reactivity, making it a valuable intermediate in medicinal chemistry and pharmaceutical research. This compound is particularly useful in the synthesis of biologically active molecules due to its structural versatility and ability to participate in further functionalization. Its well-defined molecular structure ensures consistency in downstream applications, while the hydroxymethyl group offers a convenient handle for derivatization. Suitable for use in organic synthesis and drug discovery, it exhibits favorable stability under standard laboratory conditions.
6-fluoro-Imidazo[1,2-a]pyridine-2-methanol structure
1038827-63-2 structure
Product Name:6-fluoro-Imidazo[1,2-a]pyridine-2-methanol
CAS No:1038827-63-2
MF:C8H7FN2O
MW:166.152384996414
MDL:MFCD14636530
CID:821214
PubChem ID:57690214
Update Time:2025-11-02

6-fluoro-Imidazo[1,2-a]pyridine-2-methanol Chemical and Physical Properties

Names and Identifiers

    • 6-fluoro-Imidazo[1,2-a]pyridine-2-methanol
    • (6-Fluoroimidazo[1,2-a]pyridin-2-yl)methanol
    • (6-fiuoroimidazo[1,2-a]pyridin-2-yl)methanol
    • (6-Fluoro-imidazo[1,2-a]pyridin-2-yl)-methanol
    • 6-fluoroimidazo[1,2-a]pyridine-2-methanol
    • ACT04829
    • KB-199447
    • SureCN871183
    • IMidazo[1,2-a]pyridine-2-Methanol, 6-fluoro-
    • (6-fluoroimidazo[1,2-a]pyridin-2-yl)methanol(WXC06778)
    • CS-0446082
    • DB-059066
    • DTXSID20727545
    • (6-Fluoroimidazo[1,2-a]pyridin-2-yl)-methanol
    • GQTDOTCPDYZHAH-UHFFFAOYSA-N
    • SCHEMBL871183
    • W13609
    • MFCD14636530
    • WS-01374
    • 1038827-63-2
    • MDL: MFCD14636530
    • Inchi: 1S/C8H7FN2O/c9-6-1-2-8-10-7(5-12)4-11(8)3-6/h1-4,12H,5H2
    • InChI Key: GQTDOTCPDYZHAH-UHFFFAOYSA-N
    • SMILES: FC1C=CC2=NC(CO)=CN2C=1

Computed Properties

  • Exact Mass: 166.05424101g/mol
  • Monoisotopic Mass: 166.05424101g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 1
  • Complexity: 167
  • 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
  • Topological Polar Surface Area: 37.5?2

Experimental Properties

  • Density: 1.38
  • PSA: 37.53000
  • LogP: 0.96570

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Additional information on 6-fluoro-Imidazo[1,2-a]pyridine-2-methanol

Recent Advances in the Study of 6-fluoro-Imidazo[1,2-a]pyridine-2-methanol (CAS: 1038827-63-2): A Promising Scaffold in Medicinal Chemistry

The compound 6-fluoro-Imidazo[1,2-a]pyridine-2-methanol (CAS: 1038827-63-2) has recently emerged as a significant scaffold in medicinal chemistry due to its versatile pharmacological properties. This heterocyclic structure, characterized by the presence of a fluorine atom at the 6-position and a hydroxymethyl group at the 2-position, has been the focus of numerous studies aimed at exploring its potential in drug discovery and development. The unique structural features of this molecule contribute to its ability to interact with various biological targets, making it a promising candidate for the treatment of multiple diseases.

Recent research has highlighted the role of 6-fluoro-Imidazo[1,2-a]pyridine-2-methanol in the development of novel therapeutic agents, particularly in the areas of oncology, infectious diseases, and central nervous system (CNS) disorders. The compound's ability to modulate key signaling pathways and its favorable pharmacokinetic properties have been demonstrated in preclinical studies. For instance, a 2023 study published in the Journal of Medicinal Chemistry reported that derivatives of this scaffold exhibited potent inhibitory activity against specific kinase targets implicated in cancer progression, with IC50 values in the nanomolar range.

In addition to its anticancer potential, 6-fluoro-Imidazo[1,2-a]pyridine-2-methanol has shown promise as an antimicrobial agent. A recent study in Bioorganic & Medicinal Chemistry Letters (2024) revealed that certain analogs of this compound displayed significant activity against drug-resistant bacterial strains, including methicillin-resistant Staphylococcus aureus (MRSA). The researchers attributed this activity to the molecule's ability to disrupt bacterial cell wall synthesis and inhibit essential enzymes involved in microbial metabolism.

The synthetic routes to 6-fluoro-Imidazo[1,2-a]pyridine-2-methanol have also been optimized in recent years, with several research groups reporting improved yields and selectivity. A 2023 paper in Organic Process Research & Development described a scalable, cost-effective synthesis of this scaffold using a one-pot multicomponent reaction strategy. This advancement is particularly significant for the pharmaceutical industry, as it facilitates the large-scale production of derivatives for further biological evaluation.

Structural-activity relationship (SAR) studies have provided valuable insights into the pharmacophoric features of 6-fluoro-Imidazo[1,2-a]pyridine-2-methanol that contribute to its biological activity. Computational modeling and X-ray crystallography studies have revealed that the fluorine atom at the 6-position enhances the molecule's binding affinity to target proteins through favorable electrostatic interactions, while the hydroxymethyl group at the 2-position serves as a versatile handle for further chemical modifications to optimize drug-like properties.

Looking forward, the 6-fluoro-Imidazo[1,2-a]pyridine-2-methanol scaffold presents exciting opportunities for the development of next-generation therapeutics. Current research efforts are focused on exploring its potential in targeted drug delivery systems and combination therapies. With its demonstrated versatility and the growing body of supporting evidence, this compound is poised to make significant contributions to the field of medicinal chemistry in the coming years.

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