885520-23-0 | 6-BROMO-4-FLUORO-1H-INDAZOLE

CAS:885520-23-0 | 6-BROMO-4-FLUORO-1H-INDAZOLE,Description

6-Bromo-4-fluoro-1H-indazole is a compound that falls within the class of azole heterocycles, which are characterized by a five-membered ring containing at least one nitrogen atom. Azole heterocycles are of significant interest due to their diverse range of biological activities and their applications in medicinal chemistry. The compound itself is not directly mentioned in the provided papers, but its structural relatives and synthetic methods are discussed, which can provide insights into its potential synthesis and properties.

Synthesis Analysis

The synthesis of azole derivatives, such as 6-Bromo-4-fluoro-1H-indazole, often involves the formation of the azole ring via methods like cycloaddition reactions. For instance, the synthesis of 2H-indazole derivatives is described through the 1,3-dipolar cycloaddition of 3-phenylsydnone with p-toluquinone, followed by bromination to yield bromo-indazole diones. Although the exact synthesis of 6-Bromo-4-fluoro-1H-indazole is not detailed, similar strategies could potentially be employed, utilizing appropriate precursors and substituents to introduce the bromo and fluoro groups at the desired positions on the indazole ring.

Molecular Structure Analysis

The molecular structure of azole derivatives is crucial for their biological activity. The crystal and molecular structure of a related compound, 6-bromo-5-methyl-2-phenyl-2H-indazole-4,7-dione, has been determined using single-crystal X-ray diffraction. This technique could similarly be applied to 6-Bromo-4-fluoro-1H-indazole to ascertain its precise molecular geometry, which is essential for understanding its reactivity and interaction with biological targets.

Chemical Reactions Analysis

Azole heterocycles, including indazoles, participate in a variety of chemical reactions. The regioselective synthesis of fluorosulfonyl 1,2,3-triazoles from bromovinylsulfonyl fluoride is an example of the versatility of azole compounds in chemical transformations. This suggests that 6-Bromo-4-fluoro-1H-indazole could also undergo various chemical reactions, potentially leading to the formation of sulfonate, sulfonamide, and sulfonic acid derivatives, which could be of interest for further functionalization or for the modulation of its biological activity.

Physical and Chemical Properties Analysis

The physical and chemical properties of 6-Bromo-4-fluoro-1H-indazole can be inferred from related compounds. The presence of halogen atoms, such as bromine and fluorine, typically affects the compound's lipophilicity, boiling point, and density. These properties are important for the compound's solubility and stability, which in turn influence its suitability for different applications, including medicinal chemistry. The papers provided do not directly discuss the physical and chemical properties of 6-Bromo-4-fluoro-1H-indazole, but studies on similar compounds can provide a basis for predicting these characteristics.

Scientific Research Applications

1. Anticancer, Antiangiogenic, and Antioxidant Agent

• Application Summary: A series of novel indazole derivatives has been synthesized and evaluated for anticancer, antiangiogenic, and antioxidant activities.
• Methods of Application: The synthesized compounds were assessed for their ability to hinder the viability of three human cancer cells lines, HEP3BPN 11 (liver), MDA 453 (breast), and HL 60 (leukemia), using the 3- (4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) reduction assay.
• Results: Compounds 11c and 11d showed higher inhibitory activity on the viability of HEP3BPN 11 (liver) when compared with the standard methotrexate. Compound 11c was found to be a potent antiangiogenic agent against TNFα, VEGF, and EGF, whereas 11d showed potent antiangiogenic activity against TNFα, VEGF, IGF1, TGFb, and leptin inhibition.

2. Synthesis of Indazoles

• Application Summary: Recent strategies for the synthesis of 1H- and 2H-indazoles have been summarized, including transition metal catalyzed reactions, reductive cyclization reactions, and synthesis of 2H-indazoles via consecutive formation of C–N and N–N bonds without catalyst and solvent from 2-azidobenzaldehydes and amines.
• Methods of Application: Various synthetic approaches to indazoles have been developed, including reactions under catalyst- and solvent-free conditions, Cu2O-mediated cyclization of o-haloaryl-N-tosylhydrazones, Ag-catalyzed nitration–annulation with tert-butyl nitrite, iodine-mediated intramolecular aryl and sp3 C–H amination, and metal-free reaction of aryl-hydrazones with montmorillonite K-10 under O2 atmosphere.
• Results: These methods generally produce good to excellent yields, with minimal formation of byproducts.

3. Dye-Sensitized Solar Cells (DSSCs)

• Application Summary: Indazole is a highly conjugated molecule which expands its applications to dye-sensitized solar cells (DSSCs).
• Methods of Application: 4-fluoro-1H-indazole can coordinate to metal center (such as Ir, Ln and Eu) to form either heteroleptic or homoleptic triplet photosensitizers that have an efficient ligand to metal energy transfer process.

4. Preparation of PI3 Kinase Inhibitors

• Application Summary: 4-BROMO-6-FLUORO (1H)INDAZOLE is used in the preparation of PI3 kinase inhibitors.

5. HIV Protease Inhibitors

• Application Summary: Biologically active compounds containing an indazole fragment have been investigated and applied in producing HIV protease inhibitors.

6. Serotonin Receptor Antagonists

• Application Summary: Indazole-containing heterocyclic compounds have been used in the production of serotonin receptor antagonists.

7. Aldol Reductase Inhibitors

• Application Summary: Indazole-containing heterocyclic compounds have been used in the production of aldol reductase inhibitors.

8. Acetylcholinesterase Inhibitors

• Application Summary: Indazole-containing heterocyclic compounds have been used in the production of acetylcholinesterase inhibitors.

Safety And Hazards

When handling 6-Bromo-4-fluoro-1H-indazole, it is recommended to avoid breathing mist, gas, or vapors, avoid contacting with skin and eye, use personal protective equipment, wear chemical impermeable gloves, ensure adequate ventilation, remove all sources of ignition, evacuate personnel to safe areas, and keep people away from and upwind of spill/leak.

Future Directions

The future directions of 6-Bromo-4-fluoro-1H-indazole research could involve its applications in dye-sensitized solar cells (DSSCs). Owing to the pyrazole moiety, 4-fluoro-1H-indazole can coordinate to metal center (such as Ir, Ln, and Eu) to form either heteroleptic or homoleptic triplet photosensitizers that have an efficient ligand to metal energy transfer process. Additionally, it can be used as a research tool in the pharmaceutical field for the synthesis of new drug molecules.

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