N-Benzoyl-2'-deoxy-2'-fluoroadenosine
[CAS# 136834-20-3]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Nucleotides and their analogues
• Name: N-Benzoyl-2'-deoxy-2'-fluoroadenosine
• Synonyms: N-[9-[(2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]benzamide
• Molecular Formula: C₁₇H₁₆FN₅O₄
• Molecular Weight: 373.34
• CAS Registry Number: 136834-20-3
• SMILES: C1=CC=C(C=C1)C(=O)NC2=C3C(=NC=N2)N(C=N3)[C@H]4[C@@H]([C@@H]([C@H](O4)CO)O)F

Properties

• Solubility: Insoluble (8.6E^-3 g/L) (25 °C), Calc.^*
• Density: 1.67±0.1 g/cm³ (20 °C 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2016 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

N-benzoyl-2'-deoxy-2'-fluoroadenosine is a chemically modified nucleoside that has attracted much attention for its potential applications in therapeutics and biochemical research. The compound combines the antiviral and anticancer properties of modified nucleosides with enhanced stability and functionality due to its unique structural modifications.

The development of N-benzoyl-2'-deoxy-2'-fluoroadenosine is part of a broad effort to improve nucleoside analogs for therapeutic use. The introduction of a benzoyl group at the N position of the deoxyribose sugar and a fluorine atom at the 2' position enhances the stability and biological activity of the compound. Researchers have focused on these modifications to improve efficacy and reduce degradation of the nucleoside in biological systems.

N-benzoyl-2'-deoxy-2'-fluoroadenosine has several key structural elements: This modification of the N-benzoyl group increases lipophilicity, enhancing cellular uptake and stability. The fluorine atom at the 2' position of the sugar increases the resistance of the compound to enzymatic degradation, making it more stable in biological environments.

Structural modifications of N-benzoyl-2'-deoxy-2'-fluoroadenosine enhance its ability to mimic natural nucleosides while resisting degradation. The benzoyl group increases cellular uptake, while the fluorine substitution prevents nuclease degradation. Once incorporated into DNA or RNA, the modified nucleosides disrupt normal cellular processes, resulting in antiviral or anticancer effects.

N-benzoyl-2'-deoxy-2'-fluoroadenosine has been studied for its potential to treat viral infections. The compound's stability and ability to incorporate into viral DNA make it a promising candidate for inhibiting viral replication.

This modified nucleoside has also been studied for its anticancer properties. By incorporating into the DNA of rapidly dividing cancer cells, it can induce apoptosis or inhibit cell proliferation, making it a potential candidate for chemotherapy.

In a research setting, N-benzoyl-2'-deoxy-2'-fluoroadenosine is used to study nucleic acid interactions and the effects of nucleoside modifications on DNA and RNA stability and function. Its unique properties provide insights into the behavior of nucleoside analogs in biological systems.

The 2'-fluoro substitution significantly improves resistance to enzymatic degradation. The N-benzoyl group enhances lipophilicity and improves cellular uptake. It can be used for antiviral and anticancer treatments and biochemical studies. However, the chemical synthesis of this modified nucleoside is complex and expensive. Further research is needed to optimize its therapeutic effect and minimize potential side effects.

References

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