N-Benzoyl-2'-O-(2-methoxyethyl)-5-methylcytidine
[CAS# 340162-93-8]

Identification

• Name: N-Benzoyl-2'-O-(2-methoxyethyl)-5-methylcytidine
• Synonyms: N-[1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-(2-methoxyethoxy)oxolan-2-yl]-5-methyl-2-oxopyrimidin-4-yl]benzamide
• Molecular Formula: C₂₀H₂₅N₃O₇
• Molecular Weight: 419.43
• CAS Registry Number: 340162-93-8
• SMILES: CC1=CN(C(=O)N=C1NC(=O)C2=CC=CC=C2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)OCCOC

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

N-Benzoyl-2'-O-(2-methoxyethyl)-5-methylcytidine (NBME-5-methylcytidine) is an advanced nucleoside analog with important implications for molecular biology and medicinal chemistry. The compound features benzoyl and 2-methoxyethyl modifications on the cytidine base, as well as a methyl group at the 5-position.

The synthesis of NBME-5-methylcytidine is part of an ongoing effort to develop nucleoside analogs with enhanced stability and biological activity. The compound is synthesized via benzoylation of 5-methylcytidine followed by the introduction of a 2-methoxyethyl group at the 2' position. These modifications increase the resistance of the nucleoside to enzymatic degradation and enhance its solubility in biological systems.

The discovery of NBME-5-methylcytidine stems from the need to create cytidine derivatives that are better able to resist metabolic breakdown while maintaining effective interactions with cellular targets. This allows researchers to more effectively study nucleoside analogs and explore their potential applications.

NBME-5-methylcytidine has several key applications in research: 5-methylcytidine modification is particularly important in epigenetics, where it mimics the naturally occurring 5-methylcytosine in DNA. NBME-5-methylcytidine is used to study DNA methylation patterns and their effects on gene expression. Its stability and modified structure make it an effective tool for studying the role of methylation in gene regulation.

The enhanced stability and solubility of this compound make it a valuable candidate for the development of new drugs targeting nucleic acid-related pathways. NBME-5-methylcytidine can serve as a lead compound for the design of therapeutics for diseases where DNA methylation plays a key role, such as cancer and genetic diseases.

The 2-methoxyethyl modification improves the cellular uptake of NBME-5-methylcytidine, making it useful for studying nucleoside transport mechanisms. This helps researchers understand how nucleoside analogs are taken up and utilized by cells.

NBME-5-methylcytidine is primarily used in research, but its properties suggest it has potential therapeutic applications. Its stability and ability to mimic natural nucleosides may allow its use in therapies targeting epigenetic modifications or as part of combination therapies for cancer and other diseases involving altered DNA methylation.

References

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