Synthesis and biological evaluation of thiazoline derivatives as new antimicrobial and anticancer agents.
N'-(3,4-Diarylthiazol-2(3H)-ylidene)-2-(arylthio)acetohydrazides were synthesized and evaluated for their antimicrobial activity and cytotoxicity against NIH/3T3 cells. Compound 22 bearing 1-phenyl-1H-tetrazole and p-chlorophenyl moieties was found to be the most promising antibacterial agent against Pseudomonas aeruginosa, whereas compound 23 bearing 1-phenyl-1H-tetrazole and p-bromophenyl moieties was the most promising antifungal agent against Candida albicans. The most effective derivatives were also evaluated for their cytotoxicity against C6 glioma cells. The results indicated that compound 17 bearing 1-phenyl-1H-tetrazole and nonsubstituted phenyl moieties (IC₅₀ = 8.3 ± 2.6 μg/mL) was more effective than cisplatin (IC₅₀ = 13.7 ± 1.2 μg/mL) against C6 glioma cells. Compound 17 also exhibited DNA synthesis inhibitory activity on C6 cells. Furthermore, compound 17 showed low toxicity to NIH/3T3 cells (IC₅₀ = 416.7 ± 28.9 μg/mL).
Anadolu University, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, 26470 Eskişehir, Turkey.
Mehlika Dilek
MD
Altıntop
Anadolu University, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, 26470 Eskişehir, Turkey. Electronic address: zakaplan@anadolu.edu.tr.
Zafer Asım
ZA
Kaplancıklı
Anadolu University, Faculty of Pharmacy, Department of Biochemistry, 26470 Eskişehir, Turkey.
Gülşen Akalın
GA
Ciftçi
Anadolu University, Faculty of Science, Department of Biology, 26470 Eskişehir, Turkey.
Rasime
R
Demirel
D000818:Animals; D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000494:pharmacology; D002176:Candida albicans / Q000187:drug effects; D045744:Cell Line, Tumor; D004353:Drug Evaluation, Preclinical; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D051379:Mice; D008826:Microbial Sensitivity Tests; D041681:NIH 3T3 Cells; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D017550:Spectroscopy, Fourier Transform Infrared; D013844:Thiazoles / Q000138:chemical synthesis / Q000494:pharmacology
D000890:Anti-Infective Agents; D000970:Antineoplastic Agents; D013844:Thiazoles
Antimicrobial activity; Cytotoxicity; DNA synthesis inhibitory activity; Hydrazone; Thiazoline