Catalytic Efficacy of a 2D Chemically Robust MOF for the Synthesis of Bioactive Diindolylmethane (DIM)-Based Drug Molecules

Abstract

Synthesis of biologically and pharmaceutically important drugs via organic transformations in one pot under mild conditions with efficient catalysts is of significant interest in terms of practical utility. Though metal-organic frameworks (MOFs) prove their efficiencies in various catalytic reactions, synthesis of drug molecules employing MOF catalysts is still in its early stage, in fact, restricted to only 1,4-Dihydropyridines (1,4-DHP) based drug molecules synthesis. Although the Friedel–Crafts alkylation (FCA) reaction is one of the oldest reactions with a significant impact on drug molecules synthesis, surprisingly this reaction triggered by MOF catalyst is largely unexplored. Herein, we report a robust framework, MOF: IITKGP-55, synthesized solely in aqueous medium, which exhibits its superior catalytic efficiencies for one-pot FCA reaction with the well tolerance of various substrate scopes. Most importantly, based on this catalytic reaction, three drug molecules with bioactive diindolylmethane (DIM) core are synthesized for the first time, which was never realized by employing any sort of heterogeneous catalysts. Moreover, Arundine drug is crystallized and an in-depth crystallographic analysis is performed. The superior catalytic efficiencies with excellent framework robustness highlight the potentiality of the developed framework and unwrap a new avenue for drug molecule synthesis via FCA reaction by employing heterogeneous catalysts.