Six-membered ring nucleoside solubility and antiviral activity
Find Innovative SolutionsGenerate Solutions
Solution Overview
Problem
Current antiviral drugs for coronaviruses, particularly those with five-membered sugar rings, face challenges with solubility in neutral water and organic solvents, limiting their clinical application and effectiveness, while there is a lack of research on six-membered ring-containing nucleoside drugs that could offer improved pharmacological activities.
Innovation Solution
A six-membered ring-containing nucleoside compound is developed, with a specific structural formula and a method for its preparation involving steps such as oxidation, cyanation, and debenzylation of D-ribose derivatives, using common reagents suitable for large-scale production.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If five-membered sugar ring nucleoside drugs are used, then antiviral activity is achieved, but solubility in neutral water and organic solvents is poor
Solution Approach 1:
The patent changes the fundamental structural parameter of the sugar ring from five-membered to six-membered configuration. This structural parameter change transforms the molecular properties, resulting in improved solubility in neutral water and organic solvents while maintaining antiviral activity against coronaviruses. The six-membered ring structure provides better dissolution characteristics compared to the conventional five-membered ring structure.
2Reliability
If five-membered sugar ring nucleoside drugs are used, then antiviral activity is achieved, but purification and injection dosage research are difficult
Solution Approach 1:
By changing the sugar ring structure from five-membered to six-membered configuration, the patent improves the physical and chemical properties of the nucleoside drug. This parameter change enhances solubility and facilitates purification processes, making the drug more suitable for clinical development and injection dosage research.
3Ease of manufacture
If six-membered ring structure is adopted, then solubility is improved, but pharmacological activity in vivo is unknown
Solution Approach 1:
The patent employs intermediary compounds and systematic chemical synthesis to bridge the gap between structural modification and biological activity. Through controlled synthesis of six-membered ring nucleoside compounds with specific substituents (R1 and R2 groups), the patent creates molecules that both achieve improved solubility and demonstrate antiviral activity in vivo against coronaviruses.
Applied Scientific Principles
This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.
Function Achieved in This Case
The nucleoside compound exhibits improved solubility and higher in vivo activity, potentially offering effective treatment options for coronavirus infections with a simple and efficient production process.
Implementation Method 1
the compound 2 is oxidized, substituted, cyanated, and debenzylated to obtain the nucleoside compound 7
Implementation Method 2
the compound 2 is oxidized, substituted, cyanated, and debenzylated to obtain the nucleoside compound 7
Implementation Method 3
the compound 2 is oxidized, substituted, cyanated, and debenzylated to obtain the nucleoside compound 7
Data Source
AI summary
The present application belongs to the field of chemical synthesis, and specifically relates to a six-membered ring-containing nucleoside compound and a preparation method thereof. The present application discloses a six-membered ring-containing nucleoside compound. The structural formula of the nucleoside compound 7 is:where R1 is selected from one ofwhere R2 is hydroxyl or alkynyl.