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5-Bromo-1H-indazole-3-carboxamide (CAS No. 1799421-04-7)

The compound 5-Bromo-1H-indazole-3-carboxamide (CAS No. 1799421-04-7) is a heterocyclic aromatic compound with significant potential in various fields of chemistry and pharmacology. This compound belongs to the indazole family, which is a bicyclic structure consisting of a benzene ring fused with an imidazole ring. The presence of the bromine atom at the 5-position and the carboxamide group at the 3-position imparts unique chemical and biological properties to this molecule.

Recent studies have highlighted the importance of 5-Bromo-1H-indazole-3-carboxamide in drug discovery, particularly in the development of kinase inhibitors. The indazole core is known for its ability to interact with protein kinases, making it a valuable scaffold for designing anti-cancer agents. The bromine substitution at the 5-position enhances the molecule's lipophilicity, which is crucial for improving bioavailability and target binding affinity.

Structurally, 5-Bromo-1H-indazole-3-carboxamide can be represented as follows:

C₈H₆BrN₃O

This molecular formula reflects the presence of eight carbon atoms, six hydrogen atoms, one bromine atom, three nitrogen atoms, and one oxygen atom. The compound has a molecular weight of approximately 208.0 g/mol and is characterized by its high melting point and moderate solubility in organic solvents.

The synthesis of 5-Bromo-1H-indazole-3-carboxamide typically involves a multi-step process that includes nucleophilic aromatic substitution and amidation reactions. Researchers have recently explored greener synthesis methods, such as microwave-assisted synthesis and catalytic processes, to enhance yield and reduce environmental impact.

In terms of biological activity, 5-Bromo-1H-indazole-3-carboxamide has shown promising results in inhibiting various kinases, including Aurora kinases and cyclin-dependent kinases (CDKs). These enzymes are critical in cell cycle regulation and are often overexpressed in cancer cells. By targeting these kinases, this compound exhibits potent anti-proliferative effects on cancer cell lines.

Furthermore, 5-Bromo-1H-indazole-3-carboxamide has been investigated for its potential in treating neurodegenerative diseases. Preclinical studies suggest that this compound may modulate pathways involved in inflammation and oxidative stress, which are key contributors to conditions like Alzheimer's disease.

The chemical stability of 5-Bromo-1H-indazole-3-carboxamide under physiological conditions has also been evaluated. It demonstrates good stability in aqueous solutions at neutral pH but undergoes hydrolysis under strongly acidic or basic conditions. This property is essential for designing drug delivery systems that ensure controlled release of the compound.

In conclusion, 5-Bromo-1H-indazole-3-carboxamide (CAS No. 1799421-04-7) is a versatile compound with wide-ranging applications in medicinal chemistry and materials science. Its unique structure, combined with recent advancements in synthesis and biological evaluation, positions it as a valuable tool for developing innovative therapeutic agents.

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