Efficient click chemistry towards novel 1H-1,2,3-triazole-tethered 4H-chromene−d-glucose conjugates: Design, synthesis and evaluation of in vitro antibacterial, MRSA and antifungal activities

Abstracts The series of 2-amino-7-propargyloxy-4 H -chromene-3-carbonitriles 5a-t were synthesized from corresponding 2-amino-7-phydroxy-4 H -chromene-3-carbonitriles 4a-t and propargyl bromide. Two procedures were used in these syntheses: K 2 CO 3 /acetone and NaH/DMF procedures with yields of 65–89% and 80–96%, respectively. 1 H -1,2,3-Triazole-tethered 4H-chromene− d -glucose conjugates 7a-t were synthesized using click chemistry of propargyl ethers 5a-t and tetra- O -acetyl-β- d -glucopyranosyl azide. Cu@MOF-5 was the optimal catalyst for this chemistry. The yields of 1 H -1,2,3-triazoles were 80–97.8%. All triazoles 7a-t were evaluated in vitro for anti-microorganism activities. Among tested compounds with MIC values of 1.56–6.25 μM, there were four compounds against B. subtilis , four compounds against S. aureus , and four compounds against S. epidermidis ; five compounds against E. coli , four compounds against K. pneumoniae , five compounds against P. aeruginosa , and six compounds against S. typhimurium . Compounds 7c , 7d , 7f , 7h , and 7r had MIC values of 1.56–6.25 μM for three clinical MRSA isolates. Some compounds had inhibitory activities against four fungi, including A. niger , A. flavus , C. albicans , and S. cerevisiae , with MIC values of 1.56–6.25 μM. Some 1 H -1,2,3-triazoles had comparatively low toxicity against RAW 264.7 cells.