N -(2,3,4,6-tetra- O -acetyl- β- d -glucopyranosyl)thiosemicarbazones of 6-alkoxy-2-oxo-2 H -chromene-4-carbaldehydes: synthesis, evaluation of their antibacterial, anti-MRSA, antifungal activity, and docking study

AbstractReaction of 6-alkoxy-2-oxo-2H-chromen-4-carbaldehydes withN-(2,3,4,6-tetra-O-acetyl- β-d-glucopyranosyl)thiosemicarbazide yielded corresponding thiosemicarbazones having 2H-chromen-2-one ring. In vitro evaluations showed that these 2H-chromen-2-one compounds exhibited remarkable antibacterial and antifungal activities against some typical bacteria and fungi. Representative compounds with MIC values of 0.78  − 1.56 μg/mL were6c,6g (againstS. aureus),6a,6f (againstS. epidermidis) (Gram-positive bacterial strains),6e,6g (againstE. coli),6b,6e (againstK. pneumoniae), and6d–f (againstS. typhimurium) (Gram-negative bacterial strains). Almost all thiosemicarbazones6a –g had no activity against Gram-positive bacterial strainB. subtilis at these MIC values. Some compounds had strong inhibitory activity against several bacteria, such as6b (forK. pneumoniae andS. typhimurium),6d,6e (forE. coli,K. pneumoniae, andS. typhimurium),6f (forS. aureus,E. coli, andS. typhimurium), and6g (forB. subtilis,S. aureus,E. coli, andK. pneumoniae). Some compounds had remarkable inhibitory activity against three clinical MRSA isolates with MIC values of 0.78 –6.25 μg/mL. Docking study showed that compound6g is compatible with the active site ofS. aureus DNA gyrase 2XCT, which suggested that the tested compounds inhibited the synthesis of this enzyme.

Source: Medicinal Chemistry Research - January 13, 2021 Category: Chemistry Source Type: research