Synthesis and evaluation of biological activities of 4-cyclopropyl-5-(2-fluorophenyl) arylhydrazono-2,3-dihydrothiazoles as potent antioxidant agents |
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Authors: | F Ghanbari Pirbasti Jafar Abbasi Shiran |
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Affiliation: | Department of Chemistry, Faculty of Sciences, University of Guilan, P.O. Box 41335-1914, Rasht, Iran |
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Abstract: | A new series of 4-cyclopropyl-5-(2-fluorophenyl)arylhydrazono-2,3-dihydrothiazole derivatives was synthesized via the reaction of prepared thiosemicarbazones with 2-bromo-1-cyclopropyl-2-(2-?uorophenyl)ethanone in the presence of Et3N as a catalyst through a semi Hantzsch cyclization. The optimized reaction conditions for this one-pot reaction were achieved. The products were obtained in short reaction times, high yields and high purities. Antioxidant activity of products was evaluated using DPPH (2,2-diphenyl-2-picrylhydrazyl) and ABTS 2,2-azinobis(3-ethylbenzothiazoline-sulfonate) assays. Products showed higher antioxidant activity using the ABTS method. Compounds 5c and 5g showed lower IC50 values compared with ascorbic acid as a standard. Compounds 5a–5h possessed moderate to high antioxidant activity by both methods. Also, antibacterial activity of 5a–5h was evaluated against gram-positive and gram-negative bacterial strains. None of the compounds inhibited A. hydrophila, while they had moderate to low inhibitory activity against other tested bacterial strains. |
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Keywords: | Hydrazinyl thiazole 2-bromo-1-cyclopropyl-2-(2-?uorophenyl)ethanone antioxidant DPPH ABTS antibacterial |
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