Cas no 1261729-67-2 (3-Fluoroquinolin-5-OL)

3-Fluoroquinolin-5-OL is a fluorinated quinoline derivative with notable utility in pharmaceutical and agrochemical research. Its structure, featuring a fluorine substituent at the 3-position and a hydroxyl group at the 5-position, enhances its reactivity and potential as a building block for bioactive compounds. The fluorine atom contributes to improved metabolic stability and binding affinity in drug design, while the hydroxyl group offers a versatile site for further functionalization. This compound is particularly valuable in the synthesis of heterocyclic scaffolds for medicinal chemistry applications. Its well-defined chemical properties make it a reliable intermediate for developing novel therapeutic agents and specialty chemicals.
3-Fluoroquinolin-5-OL structure
3-Fluoroquinolin-5-OL structure
Product Name:3-Fluoroquinolin-5-OL
CAS No:1261729-67-2
MF:C9H6FNO
MW:163.148445606232
MDL:MFCD18414583
CID:1016248
PubChem ID:136229134
Update Time:2025-11-01

3-Fluoroquinolin-5-OL Chemical and Physical Properties

Names and Identifiers

    • 3-fluoroquinolin-5-ol
    • 3-fluoro-1H-quinolin-5-one
    • AK164644
    • 3-Fluoro-5-hydroxyquinoline
    • 3-Fluoroquinolin-5(1H)-one
    • FCH1137999
    • AKOS025146682
    • AMY26153
    • SB67623
    • 1261729-67-2
    • DS-8630
    • CS-0186825
    • SCHEMBL23360458
    • 5-Quinolinol, 3-fluoro-
    • DB-136609
    • DTXSID60857279
    • MFCD18414583
    • 3-Fluoroquinolin-5-OL
    • MDL: MFCD18414583
    • Inchi: 1S/C9H6FNO/c10-6-4-7-8(11-5-6)2-1-3-9(7)12/h1-5,12H
    • InChI Key: LYPUHYGYYPHSOX-UHFFFAOYSA-N
    • SMILES: FC1=CN=C2C=CC=C(C2=C1)O

Computed Properties

  • Exact Mass: 163.043341977g/mol
  • Monoisotopic Mass: 163.043341977g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 0
  • Complexity: 165
  • 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: 33.1

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Additional information on 3-Fluoroquinolin-5-OL

Recent Advances in the Study of 3-Fluoroquinolin-5-OL (CAS: 1261729-67-2): A Promising Scaffold in Medicinal Chemistry

3-Fluoroquinolin-5-OL (CAS: 1261729-67-2) has emerged as a significant scaffold in medicinal chemistry due to its versatile pharmacological properties. Recent studies have highlighted its potential as a key intermediate in the synthesis of novel therapeutic agents targeting various diseases, including cancer, infectious diseases, and neurological disorders. This research brief aims to provide an overview of the latest advancements in the study of 3-Fluoroquinolin-5-OL, focusing on its synthesis, biological activities, and potential applications in drug discovery.

The quinoline nucleus, a privileged structure in medicinal chemistry, has been extensively explored for its diverse biological activities. The introduction of a fluorine atom at the 3-position and a hydroxyl group at the 5-position of the quinoline ring (as in 3-Fluoroquinolin-5-OL) has been shown to enhance its pharmacological profile. Recent synthetic methodologies have enabled the efficient production of this compound, with improved yields and purity, making it more accessible for further biological evaluation.

In the context of anticancer research, 3-Fluoroquinolin-5-OL has demonstrated promising activity against various cancer cell lines. Mechanistic studies suggest that its antiproliferative effects are mediated through the inhibition of key enzymes involved in cell cycle regulation and apoptosis. For instance, a recent study published in the Journal of Medicinal Chemistry reported that derivatives of 3-Fluoroquinolin-5-OL exhibited potent inhibitory activity against topoisomerase II, a critical target in cancer therapy.

Beyond oncology, 3-Fluoroquinolin-5-OL has also shown potential in antimicrobial applications. Researchers have synthesized a series of derivatives with enhanced activity against drug-resistant bacterial strains, including methicillin-resistant Staphylococcus aureus (MRSA) and Mycobacterium tuberculosis. These findings underscore the compound's utility in addressing the global challenge of antimicrobial resistance.

In addition to its therapeutic potential, 3-Fluoroquinolin-5-OL has been investigated for its role in neuroprotection. Preliminary studies indicate that certain derivatives can modulate neurotransmitter systems and exhibit neuroprotective effects in models of neurodegenerative diseases such as Alzheimer's and Parkinson's. These results open new avenues for the development of neuroactive drugs based on the 3-Fluoroquinolin-5-OL scaffold.

Despite these promising findings, challenges remain in optimizing the pharmacokinetic and pharmacodynamic properties of 3-Fluoroquinolin-5-OL derivatives. Future research should focus on structure-activity relationship (SAR) studies to identify the most potent and selective analogs, as well as on improving their bioavailability and reducing potential toxicity.

In conclusion, 3-Fluoroquinolin-5-OL (CAS: 1261729-67-2) represents a valuable scaffold in medicinal chemistry with broad therapeutic potential. Continued research into its synthesis, biological activities, and applications will likely yield novel drug candidates for a range of diseases. This brief highlights the importance of this compound in current drug discovery efforts and underscores the need for further investigation to fully realize its potential.

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