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  Kay S. McMillan,Anthony G. McCluskey,Annette Sorensen,Marie Boyd,Michele Zagnoni Analyst, 2016,141, 100-110
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  Brindha J.,Balamurali M. M.,Kaushik Chanda RSC Adv., 2019,9, 34720-34734
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  Ivor Lon?ari? Phys. Chem. Chem. Phys., 2015,17, 9436-9445
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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Benzopyrazoles Indazoles

3-Amino-5-chloro-1H-indazole: A Comprehensive Overview

The compound with CAS No. 5685-72-3, commonly known as 3-Amino-5-chloro-1H-indazole, is a heterocyclic aromatic compound that has garnered significant attention in the fields of organic chemistry, pharmacology, and materials science. This compound is characterized by its indazole ring system, which consists of a benzene ring fused with a pyrazole ring. The presence of an amino group (-NH2) at position 3 and a chlorine atom at position 5 imparts unique electronic and structural properties to the molecule, making it a versatile building block for various applications.

3-Amino-5-chloro-1H-indazole has been extensively studied for its potential in drug discovery. Recent research has highlighted its role as a scaffold for designing bioactive molecules targeting various therapeutic areas, including cancer, inflammation, and infectious diseases. For instance, studies have demonstrated that derivatives of this compound exhibit potent anti-proliferative activity against cancer cells by modulating key signaling pathways such as the PI3K/AKT/mTOR axis. Additionally, its ability to act as a template for designing inhibitors of enzymes like cyclin-dependent kinases (CDKs) and histone deacetylases (HDACs) further underscores its importance in medicinal chemistry.

The synthesis of 3-Amino-5-chloro-1H-indazole involves a multi-step process that typically begins with the preparation of indazole derivatives through condensation reactions of o-amino phenols with carbonyl compounds. The introduction of the chlorine substituent at position 5 is often achieved via electrophilic substitution or through the use of chlorinating agents under specific reaction conditions. Researchers have also explored alternative synthetic routes, such as microwave-assisted synthesis and catalytic methods, to enhance the efficiency and scalability of the process.

In recent years, 3-Amino-5-chloro-1H-indazole has found applications beyond traditional pharmaceuticals. Its unique electronic properties make it an attractive candidate for use in organic electronics and optoelectronic devices. For example, studies have shown that derivatives of this compound can serve as efficient electron transport materials in organic light-emitting diodes (OLEDs) and photovoltaic cells. The ability to tune its electronic properties through functionalization further expands its potential in these emerging technologies.

From a structural perspective, 3-Amino-5-chloro-1H-indazole exhibits a planar geometry due to the aromaticity of the indazole ring system. The amino group at position 3 introduces electron-donating effects, while the chlorine atom at position 5 imparts electron-withdrawing characteristics. This balance of electron-donating and withdrawing groups creates a molecule with versatile reactivity, enabling it to participate in various chemical transformations such as nucleophilic aromatic substitution, cross-coupling reactions, and hydrogen bonding interactions.

The pharmacokinetic properties of 3-Amino-5-chloro-1H-indazole have also been investigated in preclinical studies. These studies have revealed that the compound exhibits moderate solubility in aqueous solutions and demonstrates good permeability across biological membranes. However, its stability under physiological conditions remains an area of active research, as optimizing these properties is crucial for its successful translation into clinical applications.

In conclusion, 3-Amino-5-chloro-1H-indazole is a multifaceted compound with a wide range of applications in both traditional and emerging fields. Its unique chemical structure, combined with its ability to serve as a versatile building block for drug design and material science applications, positions it as an important molecule in contemporary research. As ongoing studies continue to uncover new insights into its properties and potential uses, 3-Amino-5-chloro-1H-indazole is poised to play an increasingly significant role in advancing scientific knowledge and technological innovation.

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• 61317-27-9(1H-Indazol-3-amine, 5-chloro-N,N-dimethyl-)
• 20925-60-4(4-Chloro-1H-indazol-3-amine)
• 12221-10-2(1H-Indazole-3-diazonium,6-chloro-)
• 866187-25-9(1H-Indazol-3-amine hydrochloride)
• 871709-90-9(1H-Indazole-3,6-diamine)
• 885519-32-4(6-Chloro-1H-indazol-4-amine)
• 88805-67-8(7-Chloro-1H-indazol-3-amine)