Efficient Click Chemistry Towards Novel Some Substituted 2-Amino-4-Aryl-7-Propargyloxy-4H-Chromene-3-Carbonitriles: Design, Synthesis, And Evaluation of in Vitro Antibacterial, Cytotoxic and Antifungal Activities

Abstract

A group of 2-amino-7-hydroxy-4H-chromene-3-carbonitriles 4a-e was prepared via a three-component process employing sodium carbonate as a catalyst. The experiment was conducted using a solvent mixture consisting of 96% ethanol and water, with a volume ratio of 1:20. The propargyl ether compounds 5a-e, which are derivatives of chromene-3-carbonitriles, were effectively produced by reacting the respective hydroxyl chromenes derivatives with propargyl bromide. 1H-1,2,3-Triazole-tethered click chemistry between propargyl ethers 5a-e and 1-azido-2-chlorobenzene yielded 4H-chromene-chlorophenyl conjugates 7a-e. For this chemical reaction, CuI was the best catalyst. The 1H-1,2,3-triazole yields ranged from 78.77% to 85.47 %. All triazoles 7a-e were investigated in vitro for anti-microorganism activity. Four compounds were effective against B. subtilis (MCC 2010), four compounds were effective against S. aureus (MCC 2408), four compounds were effective against P. aeruginosa and five compounds were effective against E. coli (MCC 2412).