4-(4-fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one: A Comprehensive Product Introduction
4-(4-fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one, with the CAS number 763111-47-3, is a chemical compound that has attracted significant attention in the scientific and industrial communities. This article aims to provide a detailed introduction to this product, covering its properties, uses, applications in various fields, and preparation methods.
Product Properties
4-(4-fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one is a white to off – white crystalline powder. Its molecular formula is \(C_{20}H_{17}FN_{4}O_{2}\), and the molecular weight is approximately 364.37 g/mol. The compound has a specific melting point range, which is crucial for its identification and purity assessment. The melting point of 4-(4-fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one is around [specific melting point value, if available].
In terms of solubility, it has limited solubility in water but shows better solubility in organic solvents such as dimethyl sulfoxide (DMSO), ethanol, and acetonitrile. This solubility characteristic is important for its use in various chemical and biological experiments, as well as in pharmaceutical formulations.
The chemical structure of 4-(4-fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one contains a phthalazinone core, a fluorinated benzyl group, and a piperazine – carbonyl moiety. These structural features endow the compound with unique chemical and biological properties.
Uses
Pharmaceutical Research
One of the primary uses of 4-(4-fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one is in pharmaceutical research. It has shown potential as a lead compound for the development of new drugs. The compound may interact with specific biological targets in the body, such as enzymes or receptors, to exert therapeutic effects.
For example, it may be investigated for its anti – cancer properties. Cancer is a complex disease characterized by uncontrolled cell growth and proliferation. Some studies have suggested that 4-(4-fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one can inhibit the activity of certain kinases involved in cancer cell signaling pathways. By blocking these kinases, the compound may be able to slow down or stop the growth of cancer cells.
It can also be explored for its use in the treatment of neurological disorders. The central nervous system is highly complex, and many neurological diseases, such as Alzheimer’s and Parkinson’s, lack effective treatments. 4-(4-fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one may interact with neurotransmitter receptors or ion channels in the brain, potentially modulating neuronal activity and providing therapeutic benefits.
Chemical Synthesis
In chemical synthesis, 4-(4-fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one can serve as a building block for the synthesis of more complex organic compounds. Its unique chemical structure allows it to participate in various chemical reactions, such as substitution reactions, addition reactions, and condensation reactions.
For instance, it can be used to introduce the phthalazinone and fluorinated benzyl moieties into other molecules, creating new compounds with different properties and functions. These new compounds may have applications in materials science, agrochemicals, or other fields.
Applications in Various Fields
Medical Field
In the medical field, the potential applications of 4-(4-fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one are vast. In addition to its use in drug discovery, it can also be used in diagnostic imaging. Some derivatives of this compound can be labeled with radioactive isotopes, such as technetium – 99m or fluorine – 18. These labeled compounds can then be used as radiotracers in positron emission tomography (PET) or single – photon emission computed tomography (SPECT) imaging, allowing for the visualization of specific biological processes in the body.
Furthermore, in the development of personalized medicine, 4-(4-fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one can be used to screen for patients who are most likely to respond to a particular treatment. By studying the interaction between the compound and a patient’s biological samples, such as cells or tissues, doctors can predict the effectiveness of a treatment and tailor the treatment plan to the individual patient.
Materials Science
In materials science, 4-(4-fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one can be incorporated into polymers to improve their properties. For example, it can enhance the thermal stability, mechanical strength, or electrical conductivity of polymers. The fluorine atom in the compound can increase the hydrophobicity of the polymer, making it more resistant to moisture and chemical corrosion.
It can also be used in the preparation of organic light – emitting diodes (OLEDs). The phthalazinone and piperazine – carbonyl moieties in the compound can contribute to the emission of light in the OLEDs, potentially improving their efficiency and color purity.
Agrochemicals
In the agrochemical industry, 4-(4-fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one can be developed into pesticides or herbicides. Its unique chemical structure may allow it to target specific pests or weeds while having minimal impact on non – target organisms. For example, it can act as an inhibitor of certain enzymes in pests, disrupting their metabolic processes and leading to their death.
Preparation Methods
Multi – step Synthesis
The preparation of 4-(4-fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one typically involves a multi – step synthesis process. The first step usually starts with the synthesis of the phthalazinone core. This can be achieved by reacting phthalic anhydride with hydrazine hydrate under appropriate reaction conditions, such as in the presence of a catalyst and at a specific temperature.
The next step is the introduction of the fluorinated benzyl group. This can be accomplished through a substitution reaction between the phthalazinone intermediate and a fluorinated benzyl halide. The reaction is usually carried out in an organic solvent, such as dichloromethane or toluene, and in the presence of a base, such as potassium carbonate or sodium hydroxide.
Finally, the piperazine – carbonyl moiety is introduced. This can be achieved by reacting the intermediate with piperazine – 1 – carboxylic acid or its derivatives under suitable reaction conditions, such as using a coupling agent like N,N’ – dicyclohexylcarbodiimide (DCC) or 1 – ethyl – 3-(3 – dimethylaminopropyl)carbodiimide (EDC) in the presence of a catalyst.
Optimization of Synthesis
To improve the yield and purity of 4-(4-fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one, various optimization strategies can be employed. For example, the reaction conditions, such as temperature, reaction time, and the ratio of reactants, can be carefully adjusted. The choice of solvents and catalysts also plays an important role in the synthesis process. Additionally, purification methods, such as recrystallization or column chromatography, can be used to obtain a high – purity product.
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