N-Acetyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-2'-fluorocytidine
[CAS# 159414-98-9]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Deoxynucleotides and their analogues
• Name: N-Acetyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-2'-fluorocytidine
• Synonyms: N4-Acetyl-2'-deoxy-5'-O-DMT-2'-fluorocytidine
• Molecular Formula: C₃₂H₃₂FN₃O₇
• Molecular Weight: 589.61
• CAS Registry Number: 159414-98-9
• SMILES: CC(=O)NC1=NC(=O)N(C=C1)[C@H]2[C@@H]([C@@H]([C@H](O2)COC(C3=CC=CC=C3)(C4=CC=C(C=C4)OC)C5=CC=C(C=C5)OC)O)F

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H320-H335
• Safety Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovery and Applications

N-Acetyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-2'-fluorocytidine, commonly abbreviated as acetyl-5'-O-[bis(4-MP)PhMe]-2'-dF-Cyd, is a synthetic nucleoside analog with important implications in the fields of medicinal chemistry and molecular biology. The compound represents an advanced modification of cytidine, a fundamental building block of nucleic acids, with modifications designed to enhance therapeutic efficacy and specificity in a variety of applications.

The synthesis of acetyl-5'-O-[bis(4-MP)PhMe]-2'-dF-Cyd stems from the ongoing quest to create more potent nucleoside analogs with improved pharmacological properties. The researchers aimed to create a molecule that could act as an effective inhibitor in nucleic acid synthesis while offering improved stability and selectivity over conventional nucleoside analogs.

The synthesis involves several key steps, including the introduction of a fluorine atom at the 2' position of the deoxyribose, which enhances the compound's resistance to enzymatic degradation. Addition of N-acetyl and bis(4-methoxyphenyl)benzyl groups further improves the compound's stability and potential affinity for specific biological targets.

One of the main applications of acetyl-5'-O-[bis(4-MP)PhMe]-2'-dF-Cyd is in antiviral and anticancer therapy. Structural modifications of the compound allow it to interact more effectively with viral polymerases and cancer cells, potentially improving therapeutic efficacy. In particular, its fluorinated structure can inhibit nucleic acid synthesis in pathogens or tumor cells, making it a valuable candidate for further development in these therapeutic areas.

Acetyl-5'-O-[bis(4-MP)PhMe]-2'-dF-Cyd is also being explored as a molecular probe in biochemical studies. Its unique chemical modifications make it an excellent tool for studying nucleic acid interactions, enzyme activity, and drug action mechanisms. Researchers have used it to study the binding affinity of nucleosides for various biological targets, providing insights into fundamental processes of cellular function and disease mechanisms.

In drug design, the compound's structural features can be used to develop new drugs with higher efficacy and fewer side effects. The presence of 2'-fluoro groups and bulky substituents on the nucleoside ring can be tailored to alter the interaction of the compound with the biological target, leading to the design of more selective and potent drugs.

References

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