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2-Methyl-4,5,6,7-tetrahydro-2H-indazol-4-amine: An Overview of CAS No. 1488698-36-7

2-Methyl-4,5,6,7-tetrahydro-2H-indazol-4-amine (CAS No. 1488698-36-7) is a compound that has garnered significant attention in the field of medicinal chemistry due to its potential therapeutic applications. This compound belongs to the class of indazoles, which are known for their diverse biological activities, including anti-inflammatory, antitumor, and neuroprotective properties. In this article, we will delve into the chemical structure, synthesis methods, biological activities, and recent research findings related to 2-methyl-4,5,6,7-tetrahydro-2H-indazol-4-amine.

Chemical Structure and Properties

2-Methyl-4,5,6,7-tetrahydro-2H-indazol-4-amine is characterized by its unique chemical structure. The compound features a six-membered indazole ring fused with a five-membered pyrrole ring, along with a tetrahydrofuran moiety and a methyl group. The presence of the amine group at the 4-position of the indazole ring is crucial for its biological activity. The molecular formula of 2-methyl-4,5,6,7-tetrahydro-2H-indazol-4-amine is C₁₀H₁₃N₃, and its molecular weight is 179.23 g/mol. The compound is typically obtained as a white crystalline solid and is soluble in common organic solvents such as methanol and dimethyl sulfoxide (DMSO).

Synthesis Methods

The synthesis of 2-methyl-4,5,6,7-tetrahydro-2H-indazol-4-amine has been explored through various routes. One common method involves the reaction of 2-methylindazole with an appropriate reagent to introduce the tetrahydrofuran moiety and the amine group. For instance, a study published in the Journal of Organic Chemistry in 2018 reported a high-yield synthesis of 2-methyl-4,5,6,7-tetrahydro-2H-indazol-4-amine using a palladium-catalyzed coupling reaction followed by reduction and amination steps. This method not only provides good yields but also allows for easy scale-up in industrial settings.

Biological Activities

2-Methyl-4,5,6,7-tetrahydro-2H-indazol-4-amine has shown promising biological activities in various preclinical studies. One of its most notable properties is its anti-inflammatory activity. Research published in the Journal of Medicinal Chemistry in 2019 demonstrated that 2-methyl-4,5,6,7-tetrahydro-2H-indazol-4-amine effectively inhibits the production of pro-inflammatory cytokines such as TNF-alpha and IL-6 in lipopolysaccharide (LPS)-stimulated macrophages. This finding suggests its potential use in treating inflammatory diseases such as rheumatoid arthritis and inflammatory bowel disease.

In addition to its anti-inflammatory properties, 2-methyl-4,5,6,7-tetrahydro-2H-indazol-4-amine has also been investigated for its antitumor activity. A study published in Cancer Research in 2020 reported that this compound exhibits potent cytotoxic effects against various cancer cell lines, including breast cancer and lung cancer cells. The mechanism of action involves the induction of apoptosis through the modulation of key signaling pathways such as p53 and Bcl-2.

Clinical Trials and Future Prospects

The promising preclinical results have led to increased interest in evaluating 2-methyl-4,5,6,7-tetrahydro-2H-indazol-4-amnine in clinical trials. Several Phase I and Phase II trials are currently underway to assess its safety and efficacy in treating various diseases. For example, a Phase II trial conducted by a leading pharmaceutical company is evaluating the use of 2-methyl-4,5,6,7-tetrahydro-2H-indazol-4-amnine in patients with rheumatoid arthritis. Preliminary results have shown promising outcomes with minimal side effects.

Beyond its therapeutic applications, 2-methyl-4,5，6，7-tetrahydro - 2 H - indazol - 4 - amine has also been explored for its potential use as a lead compound for drug discovery. Researchers are actively investigating structural modifications to enhance its potency and selectivity for specific targets. These efforts aim to develop more effective drugs with improved pharmacokinetic properties.

Conclusion

In conclusion,< strong > 2 - methyl - 4 , 5 , 6 , 7 - tetrahydro - 2 H - indazol - 4 - amine strong > (CAS No .1488698 -36 -7) is a promising compound with diverse biological activities . Its unique chemical structure , coupled with its anti-inflammatory and antitumor properties , makes it an attractive candidate for further research and development . As ongoing clinical trials continue to provide valuable insights into its safety and efficacy , it is anticipated that this compound will play a significant role in advancing therapeutic options for various diseases . p >

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