5'-O-[Bis(4-methoxyphenyl)(phenyl)methyl]-2'-deoxy-2'-fluorouridine
[CAS# 146954-74-7]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Deoxynucleotides and their analogues
• Name: 5'-O-[Bis(4-methoxyphenyl)(phenyl)methyl]-2'-deoxy-2'-fluorouridine
• Synonyms: 2'-Deoxy-5'-O-DMT-2'-fluorouridine
• Molecular Formula: C₃₀H₂₉FN₂O₇
• Molecular Weight: 548.56
• CAS Registry Number: 146954-74-7
• SMILES: COC1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=C(C=C3)OC)OC[C@@H]4[C@H]([C@H]([C@@H](O4)N5C=CC(=O)NC5=O)F)O

Safety Data

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

Discovery and Applications

5'-O-[bis(4-methoxyphenyl)(phenyl)methyl]-2'-deoxy-2'-fluorouridine is a chemically modified nucleoside that has attracted much attention for its potential applications in medicinal chemistry and molecular biology. This compound, often abbreviated as BPMF-DFUR, has a unique combination of structural elements that enhance its stability and functional properties.

The discovery of BPMF-DFUR stems from efforts to develop nucleoside analogs with improved biological activity and stability. The compound is synthesized through a series of chemical reactions, starting with 2'-deoxy-2'-fluorouridine. The 5'-O-[bis(4-methoxyphenyl)(phenyl)methyl] group is introduced through a selective alkylation process. This modification is intended to protect the phosphate group of the nucleoside, improving its stability and resistance to enzymatic degradation.

BPMF-DFUR has shown good promise in pharmaceutical research due to its potential as an antiviral agent. Its structural modifications can enhance binding affinity to viral targets or improve cellular uptake, making it a candidate for further investigation as a drug for the treatment of various viral infections.

In molecular biology, BPMF-DFUR can serve as a valuable tool in nucleic acid research. The fluorine atom at the 2' position of the uridine moiety facilitates its unique interaction with nucleic acid structures, potentially improving the specificity and efficiency of nucleic acid-based assays and experiments.

The stability imparted by the bis(4-methoxyphenyl)(phenyl)methyl group suggests that BPMF-DFUR can be used to develop new pharmaceutical formulations. Its ability to resist degradation is beneficial for creating drugs with longer shelf lives and more predictable pharmacokinetics.

References

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