Synthesis and antimicrobial and pharmacological properties of new thiosemicarbazide and 1,2,4‐triazole derivatives |
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| Authors: | Łukasz Popiołek Maria Dobosz Anna Chodkowska Ewa Jagiełło‐Wójtowicz Urszula Kosikowska Anna Malm Liliana Mazur Zofia Rzączyńska |
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| Affiliation: | 1. Department of Organic Chemistry, Medical University, 6 Staszica Str., 20‐081 Lublin, Poland;2. Department of Toxicology, Medical University, 8 Chod?ki Str., 20‐093 Lublin, Poland;3. Department of Pharmaceutical Microbiology, Medical University, 1 Chod?ki Str, 20‐093 Lublin, Poland;4. Department of General and Coordination Chemistry, Faculty of Chemistry, Maria Curie‐Sklodowska University, M. Curie‐Sklodowska Sq. 3, 20‐031 Lublin, Poland |
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| Abstract: | Reaction of 4‐phenyl‐4H‐1,2,4‐triazole‐3‐thione with ethyl bromoacetate has led to the formation of ethyl [(4‐phenyl‐4H‐1,2,4‐triazol‐3‐yl)sulfanyl]acetate 1 , the structure of which was confirmed by X‐ray analysis. In the next reaction with 80% hydrazide hydrate, appropriate hydrazide 2 was obtained, which in reaction with isothiocyanates was converted to new acyl derivatives of thiosemicarbazides 2 , 3 , 3a , 3b , 3c , 3d , 3e , 3f , 3g , 3h . The cyclization of these compounds in alkaline media has led to formation of new derivatives of 5‐{[(4‐phenyl‐4H‐1,2,4‐triazole‐3‐yl)sulfanyl]methyl}‐4H‐1,2,4‐triazole‐3(2H)‐thiones 4a , 4b , 4c , 4d , 4e , 4f , 4g , 4j . The structure of the compounds was confirmed by elementary analysis and IR, 1H‐NMR, 13C‐NMR, and MS spectra. Compounds 2 , 3 , 3a , 3b , 3c , 3d , 3e , 3f , 3g , 3h and 4a , 4b , 4c , 4d , 4e , 4f , 4g were screened for their antimicrobial activities, and the influence of the compounds 4a , 4b , and 4e , 4f , 4g on the central nervous system of mice in behavioral tests was examined. J. Heterocyclic Chem., (2011). |
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