AMPK Activator Compound Design for Stable, Easier Synthesis
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Solution Overview
Problem
There is a need for a novel AMP-activated protein kinase (AMPK) activator that is easy to synthesize, stable, and effective in treating conditions associated with decreased AMPK activity, such as obesity, diabetes, and cancer.
Innovation Solution
A compound represented by formula (I), where R1 is a hydrogen atom or an optionally substituted C1-20 alkyl group, R2 is an optionally substituted 5- or 6-membered monocyclic aromatic heterocyclic group, L1 is a C1-20 alkylene group optionally substituted by a hydroxy group, and L2 is a divalent group represented by *N(R3)C(═O) or *N(R3)S(O)2, with n being an integer of 1 to 10, or a pharmaceutically acceptable salt thereof, exhibits superior AMPK activating action.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If existing AMPK activators are used, then AMPK activation effect is achieved, but synthesis difficulty and handling stability are insufficient
Solution Approach 1:
The patent modifies the chemical structure parameters of AMPK activators by introducing specific substituent groups (R1-R6) at defined positions in the molecular framework. This includes varying alkyl chain lengths (C1-20), aromatic heterocyclic groups, and divalent linker groups to optimize both biological activity and synthetic accessibility. The systematic parameter variation allows identification of compounds with improved synthesis ease while maintaining AMPK activation effectiveness.
Solution Approach 2:
The invention creates composite molecular structures combining multiple functional groups (aromatic heterocycles, alkylene chains, divalent linkers with specific geometries) into a unified AMPK activator framework. This composite approach integrates the benefits of different structural elements to achieve compounds that are simultaneously effective at activating AMPK and amenable to straightforward synthesis and handling.
2Reliability
If existing AMPK activators are used, then AMPK activation effect is achieved, but compound stability and ease of handling are insufficient
Solution Approach 1:
The patent optimizes molecular stability by carefully selecting and defining parameter ranges for various structural components. The alkyl chains (C1-20), aromatic heterocyclic groups, and divalent linkers are chosen to provide appropriate molecular rigidity, lipophilicity, and metabolic stability. These parameter optimizations ensure the compounds remain stable under physiological conditions while maintaining their AMPK activation capability.
Solution Approach 2:
The invention designs compounds with structural features that enhance stability for practical use and handling. The defined molecular framework with specific substituent groups creates compounds that are sufficiently stable for storage, formulation, and administration, eliminating the handling difficulties associated with less stable activators while preserving therapeutic effectiveness.
3Reliability
If novel AMPK activator with excellent activation action is developed, then AMPK activation effectiveness is improved, but synthesis complexity may increase
Solution Approach 1:
The patent divides the AMPK activator molecule into distinct functional segments: R1-R6 substituent groups, core aromatic heterocyclic structures, alkylene linkers (L1, L2), and divalent connecting groups. This segmentation allows each component to be independently optimized and synthesized, then assembled into the final active compound. The modular structure reduces overall complexity by breaking down the synthesis into manageable steps while maintaining high AMPK activation effectiveness.
Solution Approach 2:
The invention creates a universal molecular framework that can accommodate various substituent groups and structural variations while maintaining the core AMPK activation mechanism. This multi-functional design allows a single base structure to generate multiple active compounds with different pharmacological properties, reducing the need to develop entirely new complex structures for each application.
Data Source
AI summary
The present invention aims to provide a novel AMP-activated protein kinase activator.The present invention relates to a compound represented by the formula (I):wherein each symbol is as described in the specification, or a salt thereof, or a hydrate thereof. In addition, the present invention relates to an AMP-activated protein kinase activator containing the aforementioned compound, and a medicament containing the aforementioned compound for the prophylaxis and/or treatment of cancer.