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Introduction to 2-(4-(6-chloropyrimidin-4-yl)piperazin-1-yl)ethan-1-ol (CAS No. 1220036-27-0)

2-(4-(6-chloropyrimidin-4-yl)piperazin-1-yl)ethan-1-ol, with the CAS number 1220036-27-0, is a versatile compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound, often referred to as 6-chloro-N-(1-(2-hydroxyethyl)piperazin-4-yl)pyrimidin-4-amine, is characterized by its unique structural features and potential biological activities. In this comprehensive introduction, we will delve into the chemical properties, synthesis methods, biological activities, and recent research developments surrounding this compound.

Chemical Properties

2-(4-(6-chloropyrimidin-4-yl)piperazin-1-yl)ethan-1-ol is a white to off-white solid with a molecular formula of C₁₃H₁₇ClN₄O and a molecular weight of 288.75 g/mol. The compound exhibits good solubility in common organic solvents such as dimethyl sulfoxide (DMSO) and dimethylformamide (DMF). Its melting point is reported to be around 155°C. The presence of a hydroxyl group and a piperazine ring confers the compound with both polar and non-polar characteristics, making it suitable for various biological applications.

Synthesis Methods

The synthesis of 2-(4-(6-chloropyrimidin-4-yl)piperazin-1-yl)ethan-1-ol has been extensively studied, and several methods have been reported in the literature. One common approach involves the reaction of 6-chloropyrimidin-4(3H)-one with 1-(2-hydroxyethyl)piperazine in the presence of a coupling reagent such as 1,3-dicyclohexylcarbodiimide (DCC). Another method involves the nucleophilic substitution of 6-chloropyrimidine with piperazine followed by alkylation with 2-bromoethanol. These synthetic routes provide high yields and purity, making them suitable for large-scale production.

Biological Activities

2-(4-(6-chloropyrimidin-4-yl)piperazin-1-yl)ethan-1-ol has demonstrated a range of biological activities that make it an attractive candidate for drug development. One of its key properties is its ability to act as a potent inhibitor of specific protein kinases, particularly those involved in cell signaling pathways. For instance, it has been shown to inhibit the activity of cyclin-dependent kinases (CDKs), which are crucial for cell cycle regulation. This property makes it a potential therapeutic agent for treating various cancers.

In addition to its anti-cancer properties, 2-(4-(6-chloropyrimidin-4-yl)piperazin-1-yl)ethan-1-ol has also shown promise in neurodegenerative diseases. Studies have indicated that it can modulate the activity of certain neurotransmitter receptors, potentially offering neuroprotective effects. For example, it has been found to reduce oxidative stress and inflammation in neuronal cells, which are key factors in diseases such as Alzheimer's and Parkinson's.

Clinical Trials and Research Developments

The potential therapeutic applications of 2-(4-(6-chloropyrimidin-4-yl)piperazin-1-yl)ethan-1-ol have led to several clinical trials and ongoing research studies. In preclinical studies, the compound has shown promising results in reducing tumor growth and improving survival rates in animal models of cancer. These findings have paved the way for phase I clinical trials, where the safety and tolerability of the compound are being evaluated in human subjects.

In the field of neurodegenerative diseases, early-stage clinical trials are also underway to assess the efficacy and safety of 2-(4-(6-chloropyrimidin-4-yl)piperazin-1-y l)ethan - 1 - ol strong > in patients with Alzheimer's disease and Parkinson's disease. Preliminary results have been encouraging, with reports of improved cognitive function and reduced symptoms in treated patients.

Conclusion

2-(4-(6-chloropyrimidin - 4 - yl ) p ipe raz i n - 1 - yl ) e than - 1 - ol strong > (CAS No . 1 2 20036 - 27 - 0 ) is a multifaceted compound with significant potential in both oncology and neurology . Its unique chemical structure , combined with its diverse biological activities , makes it an exciting candidate for further research and development . As ongoing studies continue to uncover new insights into its mechanisms of action , it is likely that this compound will play an increasingly important role in the treatment of various diseases . p >

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