C13-Hydroxy Oleanolic Acid Derivatives for Oxidative Stress
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Solution Overview
Problem
Current synthetic triterpenoid derivatives for treating oxidative stress and inflammation have limitations in terms of biological activity profiles and structural diversity, which hinders their effectiveness in addressing various diseases associated with these conditions.
Innovation Solution
Development of novel synthetic triterpenoid derivatives with specific structural modifications, including compounds of the formula C(C≡CH)C(O)Rb, where Rb is hydroxy, halo, amino, or mercapto, and their use in pharmaceutical compositions for treating and preventing diseases related to oxidative stress and inflammation.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If synthetic triterpenoid derivatives are developed to treat oxidative stress and inflammation, then biological activity is improved, but structural diversity is limited
Solution Approach 1:
The patent segments the triterpenoid structure into modular components with specific functional groups at defined positions (C1, C3, C13, C17, C28) that can be independently varied to generate diverse derivatives while maintaining core biological activity
Solution Approach 2:
The patent applies local quality by introducing specific functional groups (hydroxy, amino, mercapto, halo) at particular positions on the triterpenoid skeleton, where each position's substitution pattern is optimized to enhance specific biological activities while maintaining structural diversity
2Reliability
If chemical modifications are made to oleanolic acid to improve anti-inflammatory and anti-proliferative activity, then therapeutic effectiveness is enhanced, but complexity of synthesis increases
Solution Approach 1:
The patent employs preliminary action by introducing protecting groups during synthesis that are strategically removed in subsequent steps, allowing complex modifications to be performed in a controlled sequence that simplifies the overall synthetic process
Solution Approach 2:
The patent uses intermediary compounds with specific functional groups that serve as precursors for final derivative synthesis, enabling modular construction of complex molecules through standardized intermediate stages
Data Source
AI summary
Disclosed herein are novel C13-hydroxy derivatives of oleanolic acid, including those of the formula:wherein the variables are defined herein. Also provided are pharmaceutical compositions, kits and articles of manufacture comprising such compounds. Methods and intermediates useful for making the compounds, and methods of using the compounds, for example, as antioxidant inflammation modulators, and compositions thereof are also provided.