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

Zainab Kadhim Al-Khazragie; Bushra Kamel Al-Salami; ِAdnan Jassim Mohammed Al-Fartosy

doi:10.22146/ijc.72454

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

https://doi.org/10.22146/ijc.72454

Zainab Kadhim Al-Khazragie⁽¹⁾, Bushra Kamel Al-Salami⁽²⁾, ِAdnan Jassim Mohammed Al-Fartosy^(3*)

(1) Department of Chemistry, College of Science, University of Basrah, Basrah, Iraq, PO BOX 781, Basrah, Iraq
(2) Department of Chemistry, College of Science, University of Basrah, Basrah, Iraq, PO BOX 781, Basrah, Iraq
(3) Department of Chemistry, College of Science, University of Basrah, Basrah, Iraq, PO BOX 781, Basrah, Iraq
(*) Corresponding Author

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

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DOI: https://doi.org/10.22146/ijc.72454