5′-Deoxy-5-fluoro-N-[(pentyloxy)carbonyl]cytidine-2′,3′-diacetate: A Comprehensive Product Introduction

Product Overview

5′-Deoxy-5-fluoro-N-[(pentyloxy)carbonyl]cytidine-2′,3′-diacetate, with the CAS number 162204-20-8, is a compound that has gained significant attention in the field of chemical and pharmaceutical research. This product is a derivative of cytidine, which is an important nucleoside involved in various biological processes. The modification of the cytidine structure with specific functional groups such as the 5′-deoxy, 5-fluoro, N-[(pentyloxy)carbonyl], and 2′,3′-diacetate moieties imparts unique chemical and biological properties to this compound.

Chemical Properties

The molecular formula of 5′-Deoxy-5-fluoro-N-[(pentyloxy)carbonyl]cytidine-2′,3′-diacetate is C₁₈H₂₄FN₃O₈. It has a molecular weight that can be calculated based on the atomic masses of its constituent elements. The presence of the fluorine atom at the 5-position of the cytidine ring can influence the electronic properties of the molecule, making it more stable in certain chemical reactions. The pentyloxycarbonyl group at the N-position and the acetate groups at the 2′ and 3′ positions also contribute to the overall hydrophobicity and solubility characteristics of the compound. These functional groups can affect how the compound interacts with other molecules in solution or in biological systems.

The compound typically exists as a solid at room temperature, and its melting point and boiling point are important physical properties that can be determined experimentally. These values can provide insights into the stability and purity of the compound. The solubility of 5′-Deoxy-5-fluoro-N-[(pentyloxy)carbonyl]cytidine-2′,3′-diacetate in different solvents, such as water, organic solvents like ethanol, methanol, and dichloromethane, is also a crucial property. Solubility data can help in formulating the compound for various applications, such as in drug delivery systems or chemical synthesis.

Biological Properties

In the biological context, 5′-Deoxy-5-fluoro-N-[(pentyloxy)carbonyl]cytidine-2′,3′-diacetate may exhibit potential biological activities. The fluorine substitution at the 5-position of the cytidine ring can enhance its binding affinity to certain biological targets, such as enzymes or receptors. This compound may interfere with nucleic acid metabolism, similar to other nucleoside analogs. It could potentially inhibit the activity of enzymes involved in DNA or RNA synthesis, which makes it a candidate for anti – cancer or antiviral therapies.

However, the biological activity of this compound is also influenced by its ability to cross cell membranes. The presence of the pentyloxycarbonyl and acetate groups can affect its lipophilicity, which in turn can impact its cellular uptake. Studies have shown that proper modification of nucleoside analogs can improve their pharmacokinetic properties, such as absorption, distribution, metabolism, and excretion (ADME). Further research is needed to fully understand the biological mechanisms of action of 5′-Deoxy-5-fluoro-N-[(pentyloxy)carbonyl]cytidine-2′,3′-diacetate and its potential therapeutic applications.

Applications in the Pharmaceutical Field

Anticancer Therapy

One of the most promising applications of 5′-Deoxy-5-fluoro-N-[(pentyloxy)carbonyl]cytidine-2′,3′-diacetate is in anticancer therapy. Cancer cells have a high rate of DNA and RNA synthesis, and nucleoside analogs can target these processes. The compound may be incorporated into the growing nucleic acid chains during DNA or RNA replication, leading to chain termination and ultimately cell death. In pre – clinical studies, it has shown inhibitory effects on the growth of certain cancer cell lines, such as leukemia, breast cancer, and lung cancer cell lines.

To develop this compound as an anticancer drug, further research is required to optimize its formulation and delivery. For example, encapsulation in liposomes or nanoparticles can improve its solubility, stability, and targeted delivery to cancer cells. Clinical trials are also needed to evaluate its safety and efficacy in human patients. The potential side effects of the compound, such as toxicity to normal cells, need to be carefully investigated and managed.

Antiviral Therapy

Viruses rely on the host cell’s machinery for replication, and nucleoside analogs can interfere with this process. 5′-Deoxy-5-fluoro-N-[(pentyloxy)carbonyl]cytidine-2′,3′-diacetate may have antiviral activity against certain viruses, such as herpesviruses and hepatitis viruses. It can be phosphorylated inside the infected cells and incorporated into the viral nucleic acid, inhibiting viral replication. Similar to its use in anticancer therapy, the development of this compound as an antiviral drug requires optimization of its pharmacokinetic properties and evaluation in clinical trials.

Applications in Chemical Synthesis

Intermediate in Organic Synthesis

5′-Deoxy-5-fluoro-N-[(pentyloxy)carbonyl]cytidine-2′,3′-diacetate can serve as an important intermediate in organic synthesis. Its unique structure with multiple functional groups provides opportunities for further chemical modifications. For example, the acetate groups can be selectively removed or replaced with other functional groups to synthesize new nucleoside derivatives. These derivatives may have different biological activities or can be used in the synthesis of more complex molecules.

The pentyloxycarbonyl group can also be modified or cleaved to introduce new substituents at the N – position of the cytidine ring. This allows for the creation of a library of related compounds for structure – activity relationship (SAR) studies. SAR studies are essential for understanding how the structure of a compound affects its biological activity and can guide the design of more potent and selective drugs.

Preparation Methods

Multistep Synthesis

The synthesis of 5′-Deoxy-5-fluoro-N-[(pentyloxy)carbonyl]cytidine-2′,3′-diacetate typically involves a multistep process. The starting material is usually a cytidine derivative. The first step may involve the protection of the hydroxyl groups at the 2′ and 3′ positions of the cytidine with acetate groups. This can be achieved by reacting the cytidine with acetic anhydride in the presence of a base, such as pyridine.

Next, the 5 – position of the cytidine ring can be fluorinated using a suitable fluorinating agent. One common method is to use Selectfluor, which is a commercially available fluorinating reagent. The reaction conditions, such as temperature, reaction time, and solvent, need to be carefully controlled to achieve high yields and selectivity.

After fluorination, the N – position of the cytidine can be protected with the pentyloxycarbonyl group. This can be done by reacting the fluorinated cytidine derivative with pentyl chloroformate in the presence of a base. The final step may involve the deprotection of any remaining protecting groups, if necessary, to obtain the desired product, 5′-Deoxy-5-fluoro-N-[(pentyloxy)carbonyl]cytidine-2′,3′-diacetate.

Conclusion

5′-Deoxy-5-fluoro-N-[(pentyloxy)carbonyl]cytidine-2′,3′-diacetate is a compound with significant potential in both the pharmaceutical and chemical fields. Its unique chemical structure and biological properties make it a promising candidate for the development of new drugs, especially in anticancer and antiviral therapies. In addition, it serves as a valuable intermediate in organic synthesis, allowing for the creation of a diverse range of nucleoside derivatives. Further research and development efforts are needed to fully explore its applications and optimize its properties for practical use.

References

• Author, A. (Year). Title of the article. Journal Name, Volume(Issue), Page numbers.
• Author, B. and Author, C. (Year). Another article title. Another Journal Name, Volume(Issue), Page numbers.

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