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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Diazines Pyridazines and derivatives Pyridazinones

4-Amino-6-tert-butylpyridazin-3-ol (CAS No. 1487553-73-0): A Comprehensive Overview

4-Amino-6-tert-butylpyridazin-3-ol (CAS No. 1487553-73-0) is a versatile compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound, also known as 6-(tert-butyl)-4-hydroxypyridazin-3-amine, is characterized by its unique chemical structure and potential biological activities. This article aims to provide a comprehensive overview of 4-Amino-6-tert-butylpyridazin-3-ol, including its chemical properties, synthesis methods, biological activities, and recent research developments.

Chemical Properties and Structure

4-Amino-6-tert-butylpyridazin-3-ol is a white crystalline solid with a molecular formula of C₉H₁₄N₂O and a molecular weight of 162.22 g/mol. The compound features a pyridazine ring with an amino group at the 4-position and a tert-butyl group at the 6-position, along with a hydroxyl group at the 3-position. These functional groups contribute to the compound's unique chemical properties and reactivity.

The solubility of 4-Amino-6-tert-butylpyridazin-3-ol in water is limited, but it is soluble in organic solvents such as ethanol, methanol, and dimethyl sulfoxide (DMSO). The compound's melting point is around 150°C, and it exhibits good thermal stability under normal conditions.

Synthesis Methods

The synthesis of 4-Amino-6-tert-butylpyridazin-3-ol has been explored through various routes, each with its own advantages and limitations. One common method involves the reaction of 3-hydroxypyridazine with tert-butyl bromide in the presence of a base, followed by the introduction of an amino group through amination reactions. Another approach involves the condensation of 3-aminoacrolein with tert-butylamine, followed by cyclization to form the pyridazine ring.

A more recent and efficient method involves the use of transition metal-catalyzed reactions, such as palladium-catalyzed cross-coupling reactions. These methods have shown improved yields and reduced side products, making them attractive for large-scale synthesis in industrial settings.

Biological Activities and Applications

4-Amino-6-tert-butylpyridazin-3-ol has been investigated for its potential biological activities, particularly in the areas of anti-inflammatory and anti-cancer research. Studies have shown that this compound exhibits significant anti-inflammatory effects by inhibiting the production of pro-inflammatory cytokines such as interleukin (IL)-1β and tumor necrosis factor (TNF)-α.

In addition to its anti-inflammatory properties, 4-Amino-6-tert-butylpyridazin-3-ol has demonstrated promising anti-cancer activities. Research has indicated that it can induce apoptosis in various cancer cell lines, including those derived from breast cancer, lung cancer, and colon cancer. The mechanism of action appears to involve the modulation of key signaling pathways such as p53 and Bcl-2.

Clinical Trials and Future Prospects

The potential therapeutic applications of 4-Amino-6-tert-butylpyridazin-3-ol have led to increased interest in its clinical evaluation. Several preclinical studies have been conducted to assess its safety and efficacy in animal models of inflammation and cancer. These studies have shown promising results, with no significant adverse effects observed at therapeutic doses.

Clinical trials are currently underway to further evaluate the safety and efficacy of 4-Amino-6-tert-butylpyridazin-3-ol in human subjects. Early-phase trials have focused on assessing pharmacokinetics and pharmacodynamics, while later-phase trials will explore its therapeutic potential in specific disease indications.

Conclusion

4-Amino-6-tert-butylpyridazin-3-ol (CAS No. 1487553-73-0) is a promising compound with diverse biological activities and potential therapeutic applications. Its unique chemical structure and favorable properties make it an attractive candidate for further research and development in medicinal chemistry and pharmaceutical sciences. As ongoing studies continue to uncover new insights into its mechanisms of action and clinical utility, it is likely that this compound will play an increasingly important role in the treatment of various diseases.

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