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Introduction to 6-Chloro-3-iodo-4-nitro-1H-indazole (CAS No. 885519-97-1)

6-Chloro-3-iodo-4-nitro-1H-indazole, identified by its Chemical Abstracts Service (CAS) number 885519-97-1, is a heterocyclic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal research. This compound belongs to the indazole family, a class of molecules known for their diverse biological activities and potential applications in drug development. The structural features of 6-Chloro-3-iodo-4-nitro-1H-indazole, including the presence of chloro, iodo, and nitro substituents, make it a versatile scaffold for further chemical modifications and biological evaluations.

The indazole core is a fused bicyclic system consisting of a benzene ring and a pyrrole ring, which contributes to its unique electronic and steric properties. The introduction of halogen atoms at the 3-position and 6-position, along with a nitro group at the 4-position, enhances the reactivity and functionality of the molecule. These substituents not only influence the compound's solubility and metabolic stability but also play a crucial role in modulating its interactions with biological targets.

In recent years, 6-Chloro-3-iodo-4-nitro-1H-indazole has been extensively studied for its potential as an intermediate in the synthesis of bioactive molecules. The halogenated indazoles are particularly interesting due to their ability to serve as substrates for cross-coupling reactions, such as Suzuki-Miyaura, Stille, and Buchwald-Hartwig couplings. These reactions are fundamental in constructing more complex molecular architectures, enabling the development of novel therapeutic agents.

One of the most compelling aspects of 6-Chloro-3-iodo-4-nitro-1H-indazole is its utility in the discovery of new pharmacophores. Researchers have leveraged this compound to design molecules with antimicrobial, anti-inflammatory, and anticancer properties. The nitro group, in particular, can be reduced to an amine, providing a handle for further derivatization and optimization. This flexibility makes 6-Chloro-3-iodo-4-nitro-1H-indazole a valuable building block in medicinal chemistry.

Recent studies have highlighted the importance of halogenated indazoles in drug discovery. For instance, a 2022 study published in the Journal of Medicinal Chemistry demonstrated that compounds derived from 6-Chloro-3-iodo-4-nitro-1H-indazole exhibit potent activity against certain resistant bacterial strains. The study employed structure-based drug design principles to optimize the scaffold, resulting in derivatives with improved pharmacokinetic profiles. This work underscores the compound's significance in addressing emerging challenges in antimicrobial therapy.

The synthesis of 6-Chloro-3-iodo-4-nitro-1H-indazole involves multi-step organic transformations that require careful optimization to ensure high yield and purity. Common synthetic routes include nucleophilic aromatic substitution reactions to introduce the chloro and iodo substituents, followed by nitration to achieve the desired functional group at the 4-position. Advances in catalytic systems have enabled more efficient and sustainable synthetic methodologies, reducing waste and improving scalability.

The biological evaluation of 6-Chloro-3-iodo-4-nitro-1H-indazole has revealed several promising leads. In vitro assays have shown that this compound interacts with various enzymes and receptors involved in disease pathways. For example, preliminary data suggest that derivatives of 6-Chloro-3-iodo-4-nitro-1H-indazole may modulate signaling pathways associated with neurodegenerative disorders. These findings open up new avenues for exploring therapeutic interventions.

The structural versatility of 6-Chloro-3-iodo-4-nitro-1H-indazole also makes it an attractive candidate for computational studies. Molecular modeling techniques have been used to predict binding affinities and optimize interactions with target proteins. These computational approaches complement experimental efforts by providing insights into molecular recognition processes at an atomic level.

In conclusion,6-Chloro-(3-hydroxy)-4-methoxybenzoic acid (CAS No 885519) is not only a structurally intriguing compound but also a cornerstone in modern drug discovery. Its unique combination of functional groups and synthetic accessibility positions it as a key intermediate for developing novel therapeutic agents across multiple disease areas. As research continues to uncover new applications for halogenated indazoles, 885519 will undoubtedly remain at the forefront of medicinal chemistry innovation.

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• 1448259-05-9(5-Chloro-3-iodo-7-nitro-1H-indazole)
• 885519-25-5(4-Chloro-3-iodo-6-nitro-1H-indazole)
• 1000342-47-1(6-Chloro-3-iodo-5-nitro (1H)Indazole)
• 70315-69-4(3-Iodo-5-nitro-1H-indazole)
• 885520-00-3(4-Amino-6-chloro-3-iodo (1H)indazole)
• 885521-22-2(3-iodo-4-nitro-1H-indazole)