Synthesis and Antimicrobial Properties of New Thiosemicarbazide, 1,2,4-Triazole,and 1,3,4-Thiadiazole Derivatives of Sulfanylacetic Acid |
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Authors: | ?ukasz Popio?ek Urszula Kosikowska Maria Dobosz Anna Malm |
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Institution: | 1. Department of Organic Chemistry , Medical University of Lublin , Lublin , Poland;2. Department of Pharmaceutical Microbiology , Medical University of Lublin , Lublin , Poland |
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Abstract: | Abstract 1,2,4-triazole and 1,3,4-thiadiazole derivatives are still considered a viable lead structure for the synthesis of more efficient antimicrobial agents having a broad spectrum of activity. This study presents the synthesis and antimicrobial evaluation of a new series of substituted 1,2,4-triazole and 1,3,4-thiadiazole derivatives. Reaction of 4-phenyl-5-(pyridin-3-yl)-4H-1,2,4-triazole-3-thione with ethyl bromoacetate yields the corresponding ethyl acetate (1). In the subsequent reaction with 100% hydrazine hydrate, the hydrazide (2) was obtained, which was converted with isothiocyanates to new acyl derivatives of thiosemicarbazide (3a–l). The cyclization of these compounds in alkaline media resulted in the formation of new derivatives of 1,2,4-triazole (4a–i), whereas in acidic media new derivatives of 1,3,4-thiadiazole (5a,b,g) were obtained. All synthesized compounds were screened for their in vitro antimicrobial activities. |
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Keywords: | Thiosemicarbazide 1 2 4-triazole 1 3 4-thiadiazole antimicrobial activity cyclization reaction |
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