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

Jayaprakash Rao Yerrabelly, Subbanarasimhulu Porala, Venkateshwar Reddy Kasireddy, Earrawandla Janapriya Sony, and Someshswar Rao Sagurthi

Department of Chemistry, University College of Science, Saifabad, Osmania University, Hyderabad, India

 

E-mail: yjpr_19@yahoo.com

Received: 25 April 2022  Accepted: 22 August 2022

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, 1H NMR, 13C 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 IC50 values ranging from 0.11 to 1.04 µM than standard curcumin (IC50 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

Keywords: Chromone N,N-di-1,2,3-triazole; Click reaction; Anti-microbial activity; Anti-cancer activity; Molecular docking; SAR studies

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-022-02449-w

 

Chemical Papers 76 (12) 7833–7846 (2022)

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