(E)-6-Iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole
[CAS# 886230-77-9]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Indazoles
• Name: (E)-6-Iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole
• Synonyms: 6-iodo-1-(oxan-2-yl)-3-[(E)-2-pyridin-2-ylethenyl]indazole
• Molecular Formula: C₁₉H₁₈IN₃O
• Molecular Weight: 431.27
• CAS Registry Number: 886230-77-9
• SMILES: C1CCOC(C1)N2C3=C(C=CC(=C3)I)C(=N2)/C=C/C4=CC=CC=N4

Properties

• Density: 1.60

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P280-P305+P351+P338

Discovery and Applications

(E)-6-Iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole is a sophisticated compound notable for its intricate structure and diverse applications in modern chemical and pharmaceutical research. This molecule features a distinctive configuration with an iodinated indazole core, a pyridine-substituted ethenyl group, and a tetrahydro-pyran ring. The presence of these functional groups imparts a unique profile that makes the compound valuable in various scientific domains.

The discovery of (E)-6-Iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole marks a significant achievement in the field of organic chemistry. The synthesis of this compound involves several key steps, including the iodination of the indazole ring, the introduction of the ethenyl group via a pyridine substituent, and the attachment of the tetrahydro-pyran moiety. This multi-step synthesis reflects advancements in chemical methodology, allowing the construction of complex structures with precision.

One of the primary applications of (E)-6-Iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole is in medicinal chemistry. The indazole scaffold is known for its potential biological activity, including anti-inflammatory, antitumor, and antimicrobial properties. The addition of the iodine atom to the indazole ring enhances its utility by providing opportunities for further functionalization and optimization of its biological activity. The pyridine-substituted ethenyl group and the tetrahydro-pyran ring further diversify its chemical behavior and potential interactions with biological targets.

The compound's structural features make it a valuable candidate for the development of new pharmaceutical agents. For example, the iodinated indazole core can be exploited to create compounds with selective binding properties or enhanced activity against specific targets. The pyridine and tetrahydro-pyran moieties contribute to the molecule's stability and solubility, which are crucial factors in drug development and formulation.

Additionally, (E)-6-Iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole serves as an important intermediate in organic synthesis. Its complex structure allows for the construction of even more elaborate molecules, facilitating the exploration of new chemical spaces and the discovery of novel compounds with desirable properties. The molecule's versatility in synthetic chemistry highlights its role as a key building block in the creation of advanced materials and functionalized derivatives.

In the field of materials science, the incorporation of (E)-6-Iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole into polymeric systems or advanced materials can lead to the development of materials with unique optical or electronic properties. The iodinated indazole structure, combined with the pyridine and tetrahydro-pyran components, may impart special characteristics to materials, such as enhanced conductivity or specific interactions with light.

The discovery and application of (E)-6-Iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole exemplify the progress in synthetic chemistry and its impact on pharmaceutical and materials science. Its intricate structure and functional groups open avenues for diverse applications, from drug development to advanced material creation.

References

2015. Synthesis of Axitinib. Synfacts, 11(10).
DOI: 10.1055/s-0035-1560257