Antimicrobial and Cytotoxicity Evaluation of New 3-Allyl-2-iminothiazolidin-4-ones

Abstract

A series of novel 3-allyl-2-iminothiazolidin-4-one derivatives (4-17) was synthesized, through the reaction of 3-allyl-2-((3, 4-dichlorophenyl)imino)thiazolidin-4-one (3) with different aromatic aldehydes. The chemical stability of four representative thiazolidinone derivatives (3, 11, 13 and 14) was evaluated against γ-irradiation, at a radiation dose of 25 kGy. The compounds were found to be stable with no observed degradation in liquid chromatography-mass spectrometry (LC-MS) experiments. The synthesized thiazolidinone derivatives (3-17) were evaluated for their antimicrobial and anticancer activities. Among the tested compounds, compounds 5, 7, 8, 14 and 16 exhibited slight antibacterial activity against a multi-drug resistant Staphylococcus aureus (ATCC 43300 strain), at a concentration of 32 μg/mL. Compound 3 fully inhibited the growth of the fungal pathogen Cryptococcus neoformans, at a tested concentration of 32 μg/mL. Besides, compound 12 inhibited the biofilm formation of S. aureus (HG001 strain), with a percentage of 54% at a concentration of 64 μg/mL. Compared to the other tested compounds, compound 11 showed higher in vitro anticancer activity against melanoma and breast cancer cells, with growth inhibition values ranging from 42% to 73% at a concentration of 10 μM. Interestingly, only compounds 3, 8 and 16 showed weak cytotoxicity to murine fibroblast L929 cells, at a tested concentration of 100 μM. The other tested compounds were not cytotoxic to fibroblasts, which suggests the relative safety of the synthesized compounds to normal mammalian cells.