N-Benzoyl-2'-O-(2-methoxyethyl)adenosine
[CAS# 333335-93-6]

Identification

• Classification: API >> Inhibitor drug
• Name: N-Benzoyl-2'-O-(2-methoxyethyl)adenosine
• Synonyms: N-[9-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-(2-methoxyethoxy)oxolan-2-yl]purin-6-yl]benzamide
• Molecular Formula: C₂₀H₂₃N₅O₆
• Molecular Weight: 429.43
• CAS Registry Number: 333335-93-6
• SMILES: COCCO[C@@H]1[C@@H]([C@H](O[C@H]1N2C=NC3=C(N=CN=C32)NC(=O)C4=CC=CC=C4)CO)O

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P264-P270-P301+P312-P330-P501

Discovery and Applications

N-Benzoyl-2'-O-(2-methoxyethyl)adenosine (NBME-adenosine) is a well-known compound in the field of nucleoside chemistry, characterized by benzoyl and 2-methoxyethyl modifications on the adenosine base. The discovery and development of NBME-adenosine has important implications for biochemical research and therapeutic applications.

NBME-adenosine was originally synthesized as part of an effort to create modified nucleosides with enhanced properties for use in biological research. The synthesis involves the benzoylation of adenosine followed by the introduction of a 2-methoxyethyl group at the 2'-position. This modification enhances the stability and solubility of the compound, distinguishing it from its unmodified counterpart.

The discovery of NBME-adenosine stems from the development of nucleoside analogs with improved pharmacokinetic and pharmacodynamic profiles. Researchers sought to improve the stability of adenosine derivatives because unmodified adenosine is prone to rapid degradation and has limited cellular uptake.

NBME-adenosine has become an essential tool in biochemical and pharmacological research due to its unique properties. The 2-methoxyethyl group increases the compound's resistance to enzymatic hydrolysis, while the benzoyl group enhances its binding affinity for various biological targets. These modifications make NBME-adenosine a valuable probe for studying adenosine receptors and signaling pathways.

NBME-adenosine is used to study the interaction of adenosine with its receptors, specifically the A1, A2A, A2B, and A3 subtypes. By acting as a selective agonist or antagonist, it aids in understanding receptor activation and signal transduction mechanisms.

The compound serves as a lead structure for the development of new drugs targeting adenosine receptors. Its stability and modified properties make it an attractive candidate for further optimization in drug discovery programs.

The enhanced solubility and stability of NBME-adenosine facilitate its use in cellular uptake experiments, allowing researchers to explore the transport mechanisms of nucleosides and their analogs across cell membranes.

NBME-adenosine is primarily used in research, and its properties suggest that it has potential therapeutic applications. Its stability and receptor selectivity make it a candidate for the development of new treatments for diseases involving adenosine dysregulation, such as inflammatory diseases, cancer, and cardiovascular disease.

References

none