Synthesis of new 2-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-ylimino)thiazolidin-4-one derivatives as anti-MRSA and anti-H. pylori agents

Abstract

In this work, we have synthesized twenty five new 2-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-ylimino)thiazolidin-4-one derivatives bearing an aryl or heteroaryl methylene group on position 5 of thiazolidinone and evaluated their antimicrobial activity against Gram-positive and -negative bacteria as well as three metronidazole resistant Helicobacter pylori strains. Most of the compounds were very potent towards tested Gram-positive bacteria and showed an antibacterial efficacy substantially greater than ampicillin as the reference drug. However, no effectiveness was observed for the Gram-negative microorganisms. The compounds 9, 20 and 29 exhibited strong antimicrobial activity against Helicobacter pylori strains (inhibition zone > 30 mm) in 100 μg/disc and (inhibition zone > 20 mm) in 50 μg/disc. Taking these findings together, it seems that these potent antibacterial derivatives could be considered as promising agents for developing new anti-infectious drugs against microorganisms resistant to currently available antibiotics. Graphical Abstract

Recent Advances in Syntheses and Antibacterial Activity of Novel Furan Derivatives

“…Compound 77 on the reaction with chloroacetyl chloride in dry toluene at 80-90°C gave intermediate 78, which was subsequently treated with ammonium thiocyanate in refluxing ethanol to afford 2-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-ylimino)thiazolidin-4-one 79. Finally, compound 79 was reacted with respective aromatic or heteroaromatic aldehydes in the acidic conditions to obtain the final compounds 80-104 (Figure 18) [14]. The findings of the MIC testing revealed that most compounds had more potent antimicrobial effects against MRSA, S. epidermidis and B. cereus than the reference antibiotic, ampicillin and compounds 90 and 101 were the most active.…”