Cas no 887570-11-8 (4-Iodo-6-methoxy-1H-indazole)

4-Iodo-6-methoxy-1H-indazole is a heterocyclic aromatic compound featuring an indazole core substituted with an iodine atom at the 4-position and a methoxy group at the 6-position. This structure makes it a valuable intermediate in pharmaceutical and agrochemical research, particularly in the synthesis of bioactive molecules and ligands for medicinal chemistry applications. The iodine moiety offers versatility for further functionalization via cross-coupling reactions, while the methoxy group enhances solubility and modulates electronic properties. Its well-defined reactivity and stability under standard conditions make it suitable for use in controlled synthetic pathways. The compound is typically handled under inert conditions to preserve its integrity.
4-Iodo-6-methoxy-1H-indazole structure
4-Iodo-6-methoxy-1H-indazole structure
Product Name:4-Iodo-6-methoxy-1H-indazole
CAS No:887570-11-8
MF:C8H7IN2O
MW:274.058453798294
MDL:MFCD07781957
CID:840429
PubChem ID:24728564
Update Time:2025-10-29

4-Iodo-6-methoxy-1H-indazole Chemical and Physical Properties

Names and Identifiers

    • 4-Iodo-6-methoxy-1H-indazole
    • 4-Iodo-6-methoxy (1H)indazole
    • AKOS022173193
    • DTXSID80646420
    • 887570-11-8
    • MDL: MFCD07781957
    • Inchi: 1S/C8H7IN2O/c1-12-5-2-7(9)6-4-10-11-8(6)3-5/h2-4H,1H3,(H,10,11)
    • InChI Key: IQLPIJROVHZXSQ-UHFFFAOYSA-N
    • SMILES: IC1=CC(=CC2=C1C=NN2)OC

Computed Properties

  • Exact Mass: 273.96031g/mol
  • Monoisotopic Mass: 273.96031g/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: 2.2
  • Topological Polar Surface Area: 37.9?2

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Additional information on 4-Iodo-6-methoxy-1H-indazole

Recent Advances in the Study of 4-Iodo-6-methoxy-1H-indazole (CAS: 887570-11-8) in Chemical Biology and Pharmaceutical Research

The compound 4-Iodo-6-methoxy-1H-indazole (CAS: 887570-11-8) has recently emerged as a promising scaffold in chemical biology and pharmaceutical research. This heterocyclic molecule, characterized by its indazole core substituted with an iodine atom at the 4-position and a methoxy group at the 6-position, has attracted significant attention due to its versatile applications in medicinal chemistry and drug discovery. Recent studies have explored its potential as a key intermediate in the synthesis of bioactive molecules, particularly in the development of kinase inhibitors and other targeted therapies.

One of the most notable applications of 4-Iodo-6-methoxy-1H-indazole is its role in the synthesis of small-molecule inhibitors targeting various kinases. Kinases are critical regulators of cellular signaling pathways, and their dysregulation is implicated in numerous diseases, including cancer, inflammatory disorders, and neurodegenerative conditions. Researchers have utilized this compound as a building block to develop potent and selective inhibitors, leveraging its unique structural features to optimize binding affinity and pharmacokinetic properties. Recent publications highlight its incorporation into novel compounds with promising preclinical efficacy.

In addition to its utility in kinase inhibitor development, 4-Iodo-6-methoxy-1H-indazole has been investigated for its potential in radiopharmaceutical applications. The presence of the iodine atom offers opportunities for radioisotope labeling, making it a candidate for use in positron emission tomography (PET) imaging. Preliminary studies have demonstrated its ability to serve as a precursor for the synthesis of radiolabeled probes, which could aid in the non-invasive visualization of disease biomarkers and the evaluation of drug-target interactions in vivo.

Recent synthetic methodologies have also focused on improving the efficiency and scalability of 4-Iodo-6-methoxy-1H-indazole production. Advances in catalytic processes and green chemistry approaches have enabled higher yields and reduced environmental impact, addressing some of the challenges associated with its industrial-scale synthesis. These developments are particularly relevant for pharmaceutical companies seeking to incorporate this compound into large-scale drug manufacturing pipelines.

The pharmacological profile of 4-Iodo-6-methoxy-1H-indazole derivatives continues to be a subject of active research. Structure-activity relationship (SAR) studies have elucidated the importance of the iodine and methoxy substituents in modulating biological activity. For instance, modifications to these functional groups have been shown to influence selectivity toward specific kinase isoforms, offering a pathway to tailor compounds for targeted therapeutic applications. Computational modeling and high-throughput screening have further accelerated the identification of optimal derivatives with enhanced potency and reduced off-target effects.

Looking ahead, the potential of 4-Iodo-6-methoxy-1H-indazole extends beyond its current applications. Ongoing research is exploring its utility in fragment-based drug design, where its compact yet functionalized structure serves as a valuable starting point for the development of novel drug candidates. Additionally, its compatibility with diverse chemical transformations positions it as a versatile tool in the medicinal chemist's toolkit. As the field of chemical biology continues to evolve, this compound is expected to play an increasingly prominent role in the discovery of next-generation therapeutics.

In conclusion, 4-Iodo-6-methoxy-1H-indazole (CAS: 887570-11-8) represents a multifaceted compound with significant potential in drug discovery and chemical biology. Its applications span from kinase inhibitor development to radiopharmaceuticals, supported by ongoing advancements in synthetic chemistry and pharmacological research. Future studies will likely uncover additional therapeutic opportunities, solidifying its position as a key player in the pursuit of innovative medical solutions.

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