doiSerbia

Synthesis and antimicrobial activity of some new N-(aryl-oxo-alkyl)-5-arylidene-thiazolidine-2,4-diones

Stana Anca (University of Medicine and Pharmacy, Department of Pharmaceutical Chemistry, “Iuliu Haţieganu”, Cluj Napoca, Romania)
Tiperciuc Brînduşa (University of Medicine and Pharmacy, Department of Pharmaceutical Chemistry, “Iuliu Haţieganu”, Cluj Napoca, Romania)
Duma Mihaela (State Veterinary Laboratory for Animal Health and Food Safety, Cluj-Napoca, Romania)
Pîrnău Adrian (National Institute for Research and Development of Isotopic and Molecular Technologies, Cluj Napoca, Romania)
Verité Philippe (University of Medicine and Pharmacy Rouen, Faculty of Pharmacy, Department of Analytical Chemistry, Rouen Cedex, France)
Oniga Ovidiu (University of Medicine and Pharmacy, Department of Pharmaceutical Chemistry, “Iuliu Haţieganu”, Cluj Napoca, Romania)

A series of new 5-(2,6-dichlorobenzylidene)thiazolidine-2,4-dione and 5-(4-methoxy-benzylidene)thiazolidine-2,4-dione derivatives (3a-h and 5a-h) were synthesized starting from 5-arylidene-thiazolidine-2,4-dione and α-halo-ketones. The structural elucidation of the newly synthesized compounds was based on elemental analysis and spectroscopic data (MS, 1H-NMR, 13C-NMR). The synthesized compounds were screened for their antimicrobial activities against several pathogenic strains of Gram-positive and Gram-negative bacteria and one fungal strain (Candida albicans), assessed in vitro as growth inhibition diameters. Some of them displayed better inhibitory activities than that of the reference drug against the Gram-positive S. aureus, B. cereus, L. monocytogenes bacterial strains, and showed good antifungal activity against C. albicans, while the antibacterial activity against Gram-negative E. coli and S. typhimurium bacterial strains was moderate.

Keywords: 5-arylidene-thiazolidine-2, 4-dione, α-halo-ketone, antibacterial, antifungal