Synthesis, Characterization and Pharmacological Evaluation of Biphenyl Based 4-Thiazolidinones

Abstract

Background: Biphenyl based 4-thiazolidinones are found to possess a wide range of activities resulting in their synthesis. Methods: Eight molecules (VIIa-VIIh) were profoundly synthesized using four step procedures. These 4-thiazolidinone derivatives were characterized by elemental analysis (CHN) and spectral (IR and 1 H NMR) analysis. All the compounds were evaluated for their in vitro antimicrobial activity against one Gram negative strain (Escherichia coli) and two Gram positive strains (Bacillus subtilis and Staphylococcus aureus) and two fungal strains (Candida albicans and Aspergillus niger). Results: The results of antimicrobial studies revealed that compounds (VIIg) possessed moderate antifungal activity and compounds (VIIc and VIIe) showed good antibacterial activity against fungal and bacterial strain respectively. Conclusion: Compounds containing electron withdrawing groups (-NO 2 , -CI, -Br) on the aromatic ring showed improved antimicrobial activity.

The Bioactivity of Thiazolidin-4-Ones: A Short Review of the Most Recent Studies

“…Among the series of 116a-116d, Compound 116c with chloro substituent showed the antibacterial activity against E. coli practically equivalent to trimethoprim and better than trimethoprim against Acinetobacter baumannii and Streptococcus pyogenes [123]. The biphenylbased thiazolidine-4-ones (117a-117c) showed good antimicrobial against bacterial (E. coli, S. aureus, B. subtilis) and fungal (A. niger, C. albicans) strains, except 117c that exhibited moderate effect against fungal strains [124]. The Compounds 11 and 43a (Figures 7 and 18) exhibited strong antimicrobial activity against four bacterial (E. coli, K. pneumoniae, S. aureus and B. subtilis) and three fungal (A. niger, Aspergillus oryzae and C. albicans) strains with MIC = 1.5 µg/mL.…”

“…Among the series of 116a-116d, Compound 116c with chloro substituent showed the antibacterial activity against E. coli practically equivalent to trimethoprim and better than trimethoprim against Acinetobacter baumannii and Streptococcus pyogenes [123]. The biphenylbased thiazolidine-4-ones (117a-117c) showed good antimicrobial against bacterial (E. coli, S. aureus, B. subtilis) and fungal (A. niger, C. albicans) strains, except 117c that exhibited moderate effect against fungal strains [124]. Among the 3-amino-2-aryl/alkylthiazolidin-one derivatives, Compound 115 (Figure 50) showed higher inhibitory activity (inhibition zone -8-17 mm) than standard chloramphenicol (5-15 mm) to concentration 150 µg/mL against all tested strains (Proteus vulgaris, E. coli, K. pneumoniae, P. aeruginosa and S. aureus) [122].…”