Design, synthesis, and activity of 2-aminochromone core N,N-bis-1,2,3-triazole derivatives using click chemistry

Abstract

A new series of 2-aminochromone-based N,N -di-1,2,3-triazole hybrid heterocycles were synthesized in one pot from N,N -terminal dialkyne 2-aminochromone with various organo azides by following the click strategy using classical Cu(I)-catalyzed azide-alkyne [3 + 2] annulation reaction. The synthesized compounds were well characterized by using various spectral analyses such as IR, 1 H NMR, 13 C NMR, and HRMS data for their structural elucidation. All newly synthesized compounds have been investigated for anti-microbial activity against Gram-positive, Gram-negative bacteria, and fungal strains and exhibited high activity against microbial growth when compared with standard anti-bacterial agents. These derivatives were tested for anti-cancer activity against HeLa cell lines and found that all compounds exhibit good activity with IC 50 values ranging from 0.11 to 1.04 µM than standard curcumin (IC 50 4.83 ± 0.44 µM). The molecular docking studies of the synthesized compounds with the affinity of ligands toward the target protein dual-specificity tyrosine-regulated kinase 2, DYRK2 (PDB id: 5ZTN) molecular docking were shown a better Moldock score performed compared to standard. Graphic abstract Supplementary Information The online version contains supplementary material available at 10.1007/s11696-022-02449-w.