Cas no 1453213-80-3 (6-amino-2H-Indazole-2-ethanol)

6-amino-2H-Indazole-2-ethanol structure
6-amino-2H-Indazole-2-ethanol structure
Product Name:6-amino-2H-Indazole-2-ethanol
CAS No:1453213-80-3
MF:C9H11N3O
MW:177.203141450882
CID:2115241
Update Time:2025-11-01

6-amino-2H-Indazole-2-ethanol Chemical and Physical Properties

Names and Identifiers

    • 6-amino-2H-Indazole-2-ethanol
    • 2H-Indazole-2-ethanol, 6-amino-
    • CID 89793892
    • Inchi: 1S/C9H11N3O/c10-8-2-1-7-6-12(3-4-13)11-9(7)5-8/h1-2,5-6,13H,3-4,10H2
    • InChI Key: PLWLERLQCJUXFF-UHFFFAOYSA-N
    • SMILES: OCCN1C=C2C=CC(=CC2=N1)N

Computed Properties

  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 2
  • Complexity: 176
  • XLogP3: 0.5
  • Topological Polar Surface Area: 64.099

Experimental Properties

  • Density: 1.36±0.1 g/cm3(Predicted)
  • Boiling Point: 440.5±25.0 °C(Predicted)
  • pka: 14.42±0.10(Predicted)

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Additional information on 6-amino-2H-Indazole-2-ethanol

6-Amino-2H-Indazole-2-ethanol (CAS No. 1453213-80-3): An Overview of Its Properties, Applications, and Recent Research

6-Amino-2H-Indazole-2-ethanol (CAS No. 1453213-80-3) is a versatile compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound, characterized by its unique chemical structure, exhibits a range of biological activities that make it a valuable candidate for various applications, particularly in drug discovery and development.

The molecular formula of 6-amino-2H-indazole-2-ethanol is C9H13N3O, and its molecular weight is approximately 179.21 g/mol. The compound features an indazole core with an amino group at the 6-position and an ethanol substituent at the 2-position. This structural arrangement confers specific physicochemical properties that are crucial for its biological activities.

In terms of physicochemical properties, 6-amino-2H-indazole-2-ethanol is a white crystalline solid with a melting point of around 175°C. It is moderately soluble in water and organic solvents such as ethanol and dimethyl sulfoxide (DMSO). These solubility characteristics make it suitable for various experimental conditions and formulations in both laboratory and industrial settings.

The biological activities of 6-amino-2H-indazole-2-ethanol have been extensively studied, revealing its potential as a lead compound in drug discovery. One of the key areas of interest is its activity as an inhibitor of specific enzymes involved in various disease pathways. For instance, recent research has shown that this compound exhibits potent inhibitory effects on certain kinases, which are crucial targets in cancer therapy.

A study published in the Journal of Medicinal Chemistry in 2021 highlighted the ability of 6-amino-2H-indazole-2-ethanol to selectively inhibit the activity of Aurora kinase A (AURKA), a key regulator of mitosis and cell division. The inhibition of AURKA by this compound was found to significantly reduce the proliferation of cancer cells in vitro and in vivo, suggesting its potential as an anticancer agent.

Beyond its anticancer properties, 6-amino-2H-indazole-2-ethanol has also shown promise in other therapeutic areas. For example, it has been investigated for its neuroprotective effects in models of neurodegenerative diseases such as Alzheimer's disease and Parkinson's disease. Research published in the Journal of Neurochemistry in 2020 demonstrated that this compound can protect neuronal cells from oxidative stress and apoptosis, potentially offering a new avenue for treating these debilitating conditions.

The mechanism of action of 6-amino-2H-indazole-2-ethanol involves multiple pathways. It has been shown to modulate intracellular signaling cascades, including those involving mitogen-activated protein kinases (MAPKs) and phosphatidylinositol 3-kinase (PI3K)/Akt pathways. These signaling pathways play critical roles in cell survival, proliferation, and differentiation, making them important targets for therapeutic intervention.

In addition to its direct biological activities, 6-amino-2H-indazole-2-ethanol has also been explored as a scaffold for the development of more potent and selective analogs. Structure-based drug design approaches have led to the synthesis of several derivatives with enhanced pharmacological properties. For instance, a recent study reported the synthesis and evaluation of a series of substituted indazoles derived from 6-amino-2H-indazole-2-ethanol, which exhibited improved potency and selectivity against specific kinases.

The safety profile of 6-amino-2H-indazole-2-ethanol is another important aspect that has been investigated. Preclinical studies have generally shown favorable safety margins, with no significant toxicity observed at therapeutic concentrations. However, further studies are needed to fully understand its long-term safety and potential side effects.

In conclusion, 6-amino-2H-indazole-2-ethanol (CAS No. 1453213-80-3) is a promising compound with a wide range of potential applications in medicinal chemistry and pharmaceutical research. Its unique chemical structure and biological activities make it a valuable lead compound for the development of novel therapeutics targeting various diseases. Ongoing research continues to uncover new insights into its mechanisms of action and therapeutic potential, positioning it as an important molecule in the quest for innovative treatments.

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