Abstract
Novel 2-arylthiazolidin-4-one derivatives (8a-q and 11) have been synthesized in good-to-excellent yields (70-96%) by one-pot three-component condensation-cyclization reaction of aromatic or aliphatic primary amines, aromatic aldehydes, and thioglycolic acid in polypropylene glycol at 110°C temperature. The in vitro antimicrobial activity of the synthesized 2-arylthiazolidin-4-ones was investigated against a panel of six pathogenic fungal strains, a Gram-positive and three Gram-negative bacteria. Results revealed that the compounds (8a-d) bearing 3-(4-(1H-imidazolylmethyl)phenyl)-substituent displayed significant antibacterial efficacy specifically against Klebsiella pneumoniae (minimum inhibitory concentration 12.5 μg/mL). In addition, some of the synthesized compounds have also shown antimicotic activity against Sporothrix schenckii, Trichophyton mentagrophytes, and Aspergillus fumigatus at the concentration of 50 μg/mL.Graphical abstractA series of novel 2-arylthiazolidin-4-one analogues was prepared and assessed for their in vitro antimicrobial efficacy. Some of the synthesized compounds displayed significant antibacterial efficacy against Klebsiella pneumoniae and selective antimycotic activity against Trichophyton mentagrophytes.
Highlights
The increasing cases of microbial resistance pose a major concern to the scientific community and have become a threat for human life worldwide
We attempted the synthesis of 3-(4-((1H-imidazol-1-yl)methyl)phenyl)-2phenylthiazolidin-4-one (8a) by reacting 4-((1H-imidazol-1-yl)methyl)aniline (4a) with benzaldehyde and thioglycolic acid at 110°C in polyethylene glycol (PEG), as many organic transformations and multi-component reactions are reported in PEG, but surprisingly, no product formation was observed even after 24 h of the reaction
The success of the reaction in polypropylene glycol (PPG) is possibly due to its immiscibility with water, which helps in the removal of a water molecule from the reaction mixture during the formation of 4-thiazolidinone ring
Summary
The increasing cases of microbial resistance pose a major concern to the scientific community and have become a threat for human life worldwide. Biological evaluation The in vitro antibacterial activities of compounds (8a-q and 11) and standard drugs (gentamycin and ampicillin) were carried out against a Gram-positive bacterial strain viz. Staphylococcus aureus (Sa) and three Gram-negative bacteria viz. Escherichia coli (Ec), Klebsiella pneumoniae (Kp) and Pseudomonas aeruginosa (Pa). 3-(3-morpholinopropyl)-2-(4-(trifluoromethyl)phenyl)thiazolidin-4-one (11) did not show any activity against the tested microbial strains.
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