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4-Nitro-6-(1H)-indazole-carboxylic Acid (CAS No. 885519-71-1): An Overview of Its Properties, Applications, and Recent Research Developments

4-Nitro-6-(1H)-indazole-carboxylic Acid (CAS No. 885519-71-1) is a compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research due to its unique structural properties and potential therapeutic applications. This article aims to provide a comprehensive overview of the compound, including its chemical structure, physical and chemical properties, biological activities, and recent advancements in its research and development.

Chemical Structure and Properties

4-Nitro-6-(1H)-indazole-carboxylic Acid is a member of the indazole family, characterized by a nitrogen-containing heterocyclic ring system. The compound features a nitro group at the 4-position and a carboxylic acid group at the 6-position of the indazole ring. This specific arrangement of functional groups imparts unique chemical and biological properties to the molecule.

The molecular formula of 4-Nitro-6-(1H)-indazole-carboxylic Acid is C₉H₆N₃O₄, with a molecular weight of approximately 222.17 g/mol. It is a white to off-white solid at room temperature and is soluble in polar solvents such as water, methanol, and dimethyl sulfoxide (DMSO). The compound exhibits strong acidic properties due to the presence of the carboxylic acid group, making it useful in various chemical reactions and analytical techniques.

Biological Activities and Mechanisms of Action

4-Nitro-6-(1H)-indazole-carboxylic Acid has been extensively studied for its potential biological activities, particularly in the context of its anti-inflammatory and anti-cancer properties. Recent research has highlighted several key mechanisms through which this compound exerts its effects:

• Anti-Inflammatory Activity: Studies have shown that 4-Nitro-6-(1H)-indazole-carboxylic Acid can inhibit the production of pro-inflammatory cytokines such as interleukin-6 (IL-6) and tumor necrosis factor-alpha (TNF-α). This activity is attributed to its ability to modulate nuclear factor-kappa B (NF-κB) signaling pathways, which play a central role in inflammation.
• Anti-Cancer Activity: The compound has demonstrated significant cytotoxic effects against various cancer cell lines, including breast cancer, lung cancer, and colon cancer cells. Mechanistic studies suggest that 4-Nitro-6-(1H)-indazole-carboxylic Acid induces apoptosis through the activation of caspase-dependent pathways and the downregulation of anti-apoptotic proteins such as Bcl-2.
• Anti-Oxidant Activity: Research has also indicated that 4-Nitro-6-(1H)-indazole-carboxylic Acid possesses potent anti-oxidant properties, which may contribute to its protective effects against oxidative stress-related diseases. The compound can scavenge free radicals and inhibit lipid peroxidation, thereby reducing cellular damage.

Clinical Applications and Therapeutic Potential

The therapeutic potential of 4-Nitro-6-(1H)-indazole-carboxylic Acid has been explored in various preclinical models, with promising results. In animal studies, the compound has shown efficacy in reducing inflammation in models of arthritis and colitis. Additionally, it has demonstrated significant anti-tumor activity in xenograft models of human cancers.

Clinical trials are currently underway to evaluate the safety and efficacy of 4-Nitro-6-(1H)-indazole-carboxylic Acid in human patients. Early-phase trials have reported favorable safety profiles with minimal adverse effects. These findings suggest that further clinical development is warranted to explore its potential as a novel therapeutic agent for inflammatory diseases and cancer.

Synthesis and Production

The synthesis of 4-Nitro-6-(1H)-indazole-carboxylic Acid involves several steps, starting from readily available starting materials. One common synthetic route involves the condensation of 2-nitrobenzaldehyde with formamide to form 2-nitrobenzimidazolone, followed by cyclization with formic acid to yield the indazole core. Subsequent nitration at the 4-position and carboxylation at the 6-position complete the synthesis of the target compound.

The production process can be optimized for large-scale manufacturing by using efficient catalysts and reaction conditions that enhance yield and purity. Quality control measures are essential to ensure that the final product meets stringent pharmaceutical standards for purity and stability.

FUTURE DIRECTIONS AND CONCLUSIONS

The ongoing research on 4-Nitro-6-(1H)-indazole-carboxylic Acid holds great promise for advancing our understanding of its biological activities and therapeutic potential. Future studies should focus on elucidating the molecular mechanisms underlying its effects on inflammation and cancer, as well as exploring its interactions with other drugs or therapeutic modalities.

Clinical trials will be crucial in determining the safety and efficacy of 4-Nitro-6-(1H)-indazole-carboxylic Acid in human patients. If successful, this compound could represent a valuable addition to the arsenal of treatments available for inflammatory diseases and cancer.

• 885519-89-1(4-Amino-6-(1H)indazole carboxylic acid)
• 885518-55-8(Methyl 6-nitro-1H-indazole-4-carboxylate)
• 885521-14-2(3-Iodo-4-nitro-1H-indazole-6-carboxylic acid)
• 857773-68-3(6-Methyl-4-nitro-1H-indazole)
• 885519-61-9(6-Nitro-4-(1H)-indazole-carboxylic Acid)
• 883290-89-9(5-nitro-1H-indazole-7-carboxylic acid)
• 885521-11-9(3-Bromo-4-nitro-1H-indazole-6-carboxylic acid)
• 885521-17-5(3-Chloro-4-nitro-1H-indazole-6-carboxylic acid)
• 885519-63-1(3-Bromo-6-nitro-1H-indazole-4-carboxylic acid)
• 72922-61-3(Methyl 4-nitro-1H-indazole-6-carboxylate)