Reactivity Studies and Synthetic Strategies Towards the Preparation of New Hydrophilic Indirubin-Triazole-Based Compounds
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY(2024)
Abstract
Indirubin is an isomer of the blue dye indigo. It is widely used in Chinese medicine as part of therapy against many diseases and, thus, its skeleton becomes a promising candidate for new drug prototypes. Since it has low solubility, its properties could be improved through the insertion of hydrophilic and pharmacophoric groups, such as sugars bridged to 1,2,3-triazoles. Here, we report the synthesis of indirubin-based compounds evaluating two different routes: via the aldol condensation reaction of triazole-isatin derivatives with 3acetoxyindole (pathway A) and reductive coupling of isatin, followed by N-propargylation of indirubin. We also performed reactivity studies guided by density functional theory (DFT) calculations (pathway B). As a demonstration, we simulate interactions with the glycogen synthase kinase 3 beta enzyme, which is associated with neurodegenerative diseases, through both molecular docking and molecular dynamics simulations.
MoreTranslated text
Key words
indirubin reactivity,isatin functionalization,CuAAC reactions,molecular docking
AI Read Science
Must-Reading Tree
Example
![](https://originalfileserver.aminer.cn/sys/aminer/pubs/mrt_preview.jpeg)
Generate MRT to find the research sequence of this paper
Chat Paper
Summary is being generated by the instructions you defined