Synthesis, Antimicrobial, Antioxidant, Toxicity and Anticancer Activity of a New Azetidinone, Thiazolidinone and Selenazolidinone Derivatives Based on Sulfonamide

Abstract

A new series of azetidinone (Z2a-Z2e, Z2g), thiazolidinone and selenazolidinone derivatives (Z2B, Z2E, Z2B', Z2E') based on sulfonamide have been synthesized and characterized by different instrumental techniques, such as elemental analyses, FTIR, multinuclear NMR (1H, 13C) and mass spectrometry. The tested compound containing selenium (Z2E') was less toxic than its analogs containing sulfur (Z2E) based on the LD50 value determined by Dixon's up and down method. All compounds showed antibacterial properties, however, Z2E' was more active against Gram-negative bacteria: Escherichia coli and Pseudomonas aeruginosa than Gram-positive ones: Streptococcus aureus and Bacillus, with the lowest MIC value of 5 mg/mL. All compounds showed good antioxidant activity at a lower rate than the standard compound BHT (82%). More precisely, Z2b was the main compound that possess strong activity as an antioxidant (73%). MTT viability assay showed that all tested compounds had cytotoxic effects on MCF-7 cells after 72 h of treatment. Our results revealed that Z2E' and Z2E compounds possessed strong activity (IC50 = 24.8 and 90.9 µg/mL, respectively) against MCF-7 cells at a higher rate than the standard compound 5-FU (IC50 = 97.47 µg/mL). Our results indicated that Z2E' had a promising bioactive scaffold of great medicinal interest due to their numerous pharmacological and biological activities.

Keywords

• 2-azetidinone
• 4-thiazolidinone
• 4-selenazolidinone
• sulfonamide
• acute toxicity
• antioxidant
• antibacterial
• anticancer activity