Cas no 497084-48-7 (8-Quinolinol, 3-iodo-)

8-Quinolinol, 3-iodo- structure
8-Quinolinol, 3-iodo- structure
Product Name:8-Quinolinol, 3-iodo-
CAS No:497084-48-7
MF:C9H6INO
MW:271.054514408112
CID:1538780
PubChem ID:10912607
Update Time:2025-07-27

8-Quinolinol, 3-iodo- Chemical and Physical Properties

Names and Identifiers

    • 8-Quinolinol, 3-iodo-
    • 3-iodoquinolin-8-ol
    • SCHEMBL18229816
    • 3-iodo-8-quinolinol
    • 497084-48-7
    • DTXSID40448164
    • Inchi: 1S/C9H6INO/c10-7-4-6-2-1-3-8(12)9(6)11-5-7/h1-5,12H
    • InChI Key: IFMHKXXFNZUDSZ-UHFFFAOYSA-N
    • SMILES: IC1=CN=C2C(=CC=CC2=C1)O

Computed Properties

  • Exact Mass: 270.94898
  • Monoisotopic Mass: 270.94941g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • 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: 2.7
  • Topological Polar Surface Area: 33.1?2

Experimental Properties

  • PSA: 33.12

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Additional information on 8-Quinolinol, 3-iodo-

Introduction to 8-Quinolinol, 3-iodo (CAS No. 497084-48-7)

8-Quinolinol, 3-iodo, identified by its Chemical Abstracts Service (CAS) number 497084-48-7, is a specialized organic compound that has garnered significant attention in the field of medicinal chemistry and pharmaceutical research. This compound belongs to the quinoline family, a class of heterocyclic aromatic compounds known for their diverse biological activities and applications in drug development. The structural uniqueness of 8-Quinolinol, 3-iodo lies in its iodinated quinolinol core, which makes it a valuable intermediate in synthetic chemistry and a potential candidate for exploring novel therapeutic agents.

The iodine substituent at the 3-position of the quinolinol scaffold introduces a high reactivity that facilitates various chemical transformations, making it a versatile building block for medicinal chemists. In recent years, the interest in halogenated quinolines has surged due to their enhanced binding affinity and metabolic stability compared to their non-halogenated counterparts. This has positioned 8-Quinolinol, 3-iodo as a key intermediate in the synthesis of small-molecule inhibitors targeting various diseases, including cancer and infectious disorders.

One of the most compelling aspects of 8-Quinolinol, 3-iodo is its role in the development of kinase inhibitors. Kinases are enzymes that play crucial roles in cell signaling pathways, and their dysregulation is often associated with several diseases, particularly cancer. Researchers have leveraged the structural features of 8-Quinolinol, 3-iodo to design molecules that selectively inhibit aberrant kinase activity. For instance, studies have demonstrated its utility in generating inhibitors targeting Bruton's tyrosine kinase (BTK), which is relevant in treating B-cell malignancies such as chronic lymphocytic leukemia (CLL). The iodine atom at the 3-position allows for further derivatization via cross-coupling reactions like Suzuki-Miyaura or Stille couplings, enabling the construction of complex drug candidates with improved pharmacokinetic profiles.

Moreover, 8-Quinolinol, 3-iodo has been explored in the context of antimicrobial applications. The quinoline scaffold is well-documented for its activity against a broad spectrum of pathogens, including bacteria and fungi. The introduction of an iodine atom can modulate the electronic properties of the molecule, enhancing its interaction with microbial targets. Recent studies have highlighted its potential in combating multidrug-resistant strains by interfering with essential bacterial processes such as DNA replication and protein synthesis. This underscores the compound's significance in addressing emerging infectious challenges where traditional antibiotics are becoming less effective.

The synthetic accessibility of 8-Quinolinol, 3-iodo also contributes to its prominence in research. The compound can be synthesized through well-established methods involving halogenation and functional group interconversion strategies. This accessibility allows researchers to rapidly explore derivatives and optimize lead structures without excessive synthetic hurdles. Additionally, advances in computational chemistry have enabled virtual screening of 8-Quinolinol, 3-iodo derivatives to identify promising candidates for experimental validation. Such integrative approaches combining experimental synthesis with computational modeling have accelerated the discovery pipeline for novel therapeutics.

In conclusion, 8-Quinolinol, 3-iodo (CAS No. 497084-48-7) represents a fascinating compound with multifaceted applications in medicinal chemistry and drug development. Its unique structural features and reactivity make it an invaluable tool for designing innovative therapeutic agents targeting various diseases. As research continues to uncover new biological functions and synthetic methodologies, the potential of 8-Quinolinol, 3-iodo is expected to expand further, solidifying its role as a cornerstone in modern pharmaceutical innovation.

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