• 1. Preparation, biological evaluation and QSAR analysis of urea substituted 2,4-diamino-pyrimidine anti-malarials
  Borvornwat Toviwek,Jennifer Riley,Nicole Mutter,Mark Anderson,Lauren Webster,Irene Hallyburton,Duangkamol Gleeson,Kevin D. Read,M. Paul Gleeson RSC Med. Chem. 2022 13 1587
• 2. Design, synthesis and biological evaluation of indazole–pyrimidine based derivatives as anticancer agents with anti-angiogenic and antiproliferative activities
  Nevine M. Y. Elsayed,Dalal A. Abou El Ella,Rabah A. T. Serya,Mai F. Tolba,Raed Shalaby,Khaled A. M. Abouzid Med. Chem. Commun. 2016 7 881
• 3. Cu-catalyzed arylation of the amino group in the indazole ring: regioselective synthesis of pyrazolo-carbazoles
  K. Anil Kumar,Prakash Kannaboina,Devendra K. Dhaked,Ram A. Vishwakarma,Prasad V. Bharatam,Parthasarathi Das Org. Biomol. Chem. 2015 13 1481
• 4. A novel substrate directed multicomponent reaction for the syntheses of tetrahydro-spiro[pyrazolo[4,3-f]quinoline]-8,5′-pyrimidines and tetrahydro-pyrazolo[4,3-f]pyrimido[4,5-b]quinolines via selective multiple C–C bond formation under metal-free conditions
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• 5. Advancements in the synthesis of fused tetracyclic quinoline derivatives
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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Benzopyrazoles Indazoles

5-Amino-1H-indazole (CAS No. 19335-11-6): A Key Intermediate in Modern Pharmaceutical Research

5-Amino-1H-indazole, identified by the Chemical Abstracts Service Number (CAS No.) 19335-11-6, is a heterocyclic organic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal research. As a versatile intermediate, it serves as a building block for the synthesis of various bioactive molecules, including pharmaceuticals and agrochemicals. The indazole core, characterized by a fused benzene and pyrrole ring system, imparts unique electronic and steric properties that make it valuable for designing compounds with specific biological activities.

The structural framework of 5-amino-1H-indazole consists of an indazole ring substituted with an amino group at the 5-position. This substitution pattern enhances its reactivity, allowing for further functionalization through various chemical transformations. The compound’s ability to participate in nucleophilic substitution reactions, cyclizations, and condensation reactions makes it a preferred choice for synthetic chemists aiming to develop novel molecular architectures.

In recent years, 5-amino-1H-indazole has been extensively studied for its potential applications in drug discovery. Its indazole scaffold is a common motif in natural products and pharmacologically active compounds, contributing to its widespread use in medicinal chemistry. One notable area of research involves the development of anticancer agents, where indazole derivatives have shown promising inhibitory effects on kinases and other enzymes involved in tumor progression.

Recent advancements in computational chemistry have further highlighted the significance of 5-amino-1H-indazole as a pharmacophore. Molecular docking studies have demonstrated that indazole derivatives can interact with target proteins through hydrophobic and hydrogen bonding interactions, making them ideal candidates for structure-based drug design. These studies have paved the way for the development of more targeted and effective therapeutic agents.

Moreover, 5-amino-1H-indazole has been explored in the synthesis of antimicrobial compounds. The indazole core exhibits broad-spectrum activity against bacterial and fungal pathogens, making it a valuable component in the design of novel antibiotics. Researchers have reported the successful incorporation of 5-amino-1H-indazole into peptidomimetic molecules that mimic natural antimicrobial peptides, offering a new strategy for combating resistant strains of microorganisms.

The compound’s role in central nervous system (CNS) drug development is another area of growing interest. Indazole derivatives have been investigated for their potential as serotonin receptor modulators, which are crucial for treating neurological disorders such as depression and anxiety. Preclinical studies have shown that certain indazole-based compounds exhibit significant therapeutic effects without the side effects associated with traditional serotonin reuptake inhibitors.

From a synthetic chemistry perspective, 5-amino-1H-indazole offers numerous advantages as a starting material. Its relatively simple structure allows for easy modification through cross-coupling reactions, such as Suzuki-Miyaura and Buchwald-Hartwig couplings, which are widely used in pharmaceutical synthesis. Additionally, the compound’s stability under various reaction conditions makes it suitable for large-scale production processes.

The agrochemical industry has also recognized the potential of 5-amino-1H-indazole as a precursor for developing novel pesticides and herbicides. Derivatives of this compound have been shown to exhibit insecticidal and fungicidal properties, providing farmers with effective tools to protect their crops from pests and diseases.

In conclusion, 5-amino-1H-indazole (CAS No. 19335-11-6) is a multifaceted compound with broad applications in pharmaceuticals, agrochemicals, and materials science. Its unique structural features and reactivity make it an indispensable intermediate in synthetic chemistry. As research continues to uncover new biological activities and synthetic methodologies, the importance of 5-amino-1H-indazole is expected to grow further, solidifying its position as a cornerstone in modern chemical research.

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• 777802-08-1(1H-Indazole-5,7-diamine)
• 918903-47-6(2H-Indazol-7-amine)
• 6967-12-0(6-Amino-1H-indazole)
• 21443-96-9(1H-Indazol-7-amine)
• 41748-71-4(1H-indazol-4-amine)
• 64309-76-8(5-Aminoindazole Hydrochloride)
• 918903-42-1(2H-Indazol-5-amine)