N6-Benzoyl-2'-O-methyladenosine
[CAS# 85079-00-1]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Deoxynucleotides and their analogues
• Name: N6-Benzoyl-2'-O-methyladenosine
• Synonyms: N-[9-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]purin-6-yl]benzamide
• Molecular Formula: C₁₈H₁₉N₅O₅
• Molecular Weight: 385.37
• CAS Registry Number: 85079-00-1
• SMILES: CO[C@@H]1[C@@H]([C@H](O[C@H]1N2C=NC3=C(N=CN=C32)NC(=O)C4=CC=CC=C4)CO)O

Properties

• Solubility: Practically insoluble (0.022 g/L) (25 ºC), Calc.^*
• Density: 1.59±0.1 g/cm³ (20 ºC 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2015 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovory and Applicatios

N6-Benzoyl-2'-O-methyladenosine (Bz-2'-OMe-Ado) is a synthetic adenosine nucleoside derivative first synthesized in the early 2000s as part of research into modifying nucleoside structures for biochemical and therapeutic purposes. The compound features a benzoyl group at the nitrogen-6 position of the adenosine base and a 2'-O-methyl group on the ribose sugar, providing a unique combination of structural modifications.

The discovery of Bz-2'-OMe-Ado stems from the search for nucleoside analogs with enhanced stability and biological activity. Researchers aimed to modify the adenosine molecule to improve its pharmacological properties and investigate its potential as a therapeutic agent. The introduction of the benzoyl group was intended to stabilize the nucleoside and protect it from enzymatic degradation, while the 2'-O-methyl modification was intended to enhance its interaction with biological targets.

The synthesis of Bz-2'-OMe-Ado involves several key steps. First, adenosine is reacted with benzoyl chloride to introduce a benzoyl group at the N6 position. Subsequently, the 2'-hydroxyl group of the ribose is methylated using a methylating agent. This multi-step synthetic approach ensures the selective introduction of functional groups, resulting in a high purity of the final compound.

Bz-2'-OMe-Ado shows promise in various fields of research and application. As a nucleoside analog, Bz-2'-OMe-Ado has been investigated for its potential use in antiviral and anticancer treatments. These modifications enhance its binding affinity to adenosine receptors and other nucleic acid targets, making it a candidate for further development in drug design.

In biochemical studies, Bz-2'-OMe-Ado is a valuable tool for studying nucleoside metabolism and enzyme interactions. Its stability and modified structure allow researchers to explore the effects of adenosine analogs on cellular processes and enzyme activities.

The enhanced stability and bioactivity of this compound make it a candidate for therapeutic applications, especially in the development of drugs targeting specific biological pathways or diseases associated with adenosine signaling.