Synthesis and Antimicrobial Activity of New 3-Allyl-1,3-Thiazolidin-4-Ones

Augusta Ževžikovienė¹, Andrejus Ževžikovas¹, Eduardas Tarasevičius², Liudas Šlepikas², Konradas Vitkevičius¹

¹Department of Analytical and Toxicological Chemistry, Medical Academy, Lithuanian University of Health Sciences, ²Department of Drug Chemistry, Medical Academy, Lithuanian University of Health Sciences, Lithuania

Key words: synthesis; thiazolidin-4-one; antibacterial activity; antifungal activity.

Summary. Background and Objective. Heterocycles are one of the most important compounds in organic chemistry. Growing attention has been paid to the derivatives of thiazole, which are biologically important compounds and are useful antimicrobial and antifungal agents. Because of the structure of 1,3-thiazolidin-4-one, it is possible to obtain new biologically active compounds by introducing substitutes at various positions of 1,3-thiazolidin-4-one ring. By incorporating nitrofuran as a pharmacophore into 5 position of 4-thiazolidone ring and allyl group into 3 position, new compounds having antimicrobial activity were expected to be designed.

Material and Methods. New compounds were synthesized in several steps: synthesis of 4-allylthiosemicarbazide, then addition of aldehyde to obtain semicarbazone, and synthesis of 3-allyl- 1,3-thiazolidin-4-one ring. Furaldehyde, 5-nitrofuraldehyde, and 5-nitro-2-furylacroleine was used as pharmacophores. Antimicrobial (antifungal) activity was tested in vitro in Mueller-Hinton agar against standard bacteria cultures – Staphylococcus aureus ATCC 25923, Enterococcus faecalis ATCC 29212, Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853, Klebsiella pneumoniae ATCC 33499, Proteus mirabilis ATCC 12459, Bacillus subtilis ATCC 6633, and Bacillus cereus ATCC 8035 – and standard fungal culture – Candida albicans ATCC 60193.

Results. The results of microbial activity showed that all new compounds could be characterized as antimicrobial and antifungal agents. None of the tested compounds showed activity against Pseudomonas aeruginosa. The minimum bactericidal concentration varied in the range of 1–250 μg/mL. The compounds with the nitro group in their structure showed a higher antimicrobial and antifungal activity.

Conclusion. Five new derivatives of 3-allyl-1,3-thiazolidin-4-one with antimicrobial and antifungal activity were synthesized.

Correspondence to A. Ževžikovienė, Department of Analytical and Toxicological Chemistry, Medical Academy, Lithuanian University of Health Sciences, A. Mickevičiaus 9, 44307 Kaunas, Lithuania. E-mail: augustazev@gmail.com

Received 20 September 2010, accepted 23 August 2011