5'-O-[Bis(4-methoxyphenyl)phenylmethyl]-2'-O-(2-methoxyethyl)-5-methyluridine
[CAS# 163759-50-0]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound
• Name: 5'-O-[Bis(4-methoxyphenyl)phenylmethyl]-2'-O-(2-methoxyethyl)-5-methyluridine
• Synonyms: 1-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxy-3-(2-methoxyethoxy)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• Molecular Formula: C₃₄H₃₈N₂O₉
• Molecular Weight: 618.67
• CAS Registry Number: 163759-50-0
• SMILES: CC1=CN(C(=O)NC1=O)[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)OCCOC

Properties

• Density: 1.32

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319
• Safety Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Discovery and Applications

5'-O-[bis(4-methoxyphenyl)benzyl]-2'-O-(2-methoxyethyl)-5-methyluridine, commonly abbreviated 5'-O-[bis(4-MP)PhMe]-2'-O-(2-ME)-5-MeU, is a highly modified nucleoside with promising applications in biochemical research and therapeutic development. The compound represents an advanced advancement in nucleoside chemistry, combining multiple structural modifications to enhance stability and functionality.

The synthesis of 5'-O-[bis(4-MP)PhMe]-2'-O-(2-ME)-5-MeU stems from an effort to create nucleoside analogs with superior stability and biological activity. By modifying the ribose sugar with a bis(4-methoxyphenyl)benzyl group at the 5' position and a 2-methoxyethyl group at the 2' position, the researchers aimed to obtain a nucleoside with enhanced resistance to enzymatic degradation and improved cellular uptake. Additionally, a 5-methyl group was introduced on the uridine base to further improve stability and binding affinity.

The synthesis of this compound involves multiple steps: attachment of a bis(4-methoxyphenyl)benzyl group to the 5' position, addition of a 2-methoxyethyl group to the 2' position, and incorporation of a 5-methyl group to the uridine base. Each modification affects the overall stability and biological activity of the compound.

5'-O-[Bis(4-MP)PhMe]-2'-O-(2-ME)-5-MeU shows potential as an antiviral and anticancer therapeutic. Chemical modifications enhance its stability and efficacy as an inhibitor of nucleic acid synthesis in viruses and cancer cells. Its ability to resist enzymatic breakdown makes it a candidate for further development in the treatment of diseases involving rapid cell division or viral replication.

In RNA research, this nucleoside analog is used to create stable RNA molecules for a variety of applications. The 2-methoxyethyl group enhances RNA stability, while the bulky substituent at the 5' position can affect RNA folding and interactions. This makes it a valuable tool for studying RNA structure-function relationships and developing RNA-based therapeutics with improved stability and functionality.

The unique structural features of this compound provide opportunities for drug design. By exploiting the stability and selectivity afforded by chemical modifications, researchers can design new drugs with better pharmacokinetic properties and fewer side effects. The ability of this nucleoside analog to specifically interact with biological targets could lead to innovative therapeutic approaches with enhanced therapeutic effects.

References

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