Synthesis and properties of 5-(((5-amino-1,3,4-thiadiazole-2-yl)thio)methyl)-4-phenyl-1,2,4-triazole-3-thione and its some S-derivatives
Increased attention to thiadiazole and 1,2,4-triazole derivatives is determined by the extensive structural modification capabilities of heterocyclic system derivatives and their high pharmacological potential. Synthesis of new molecules containing, along with the 1,2,4-triazole moiety, thiadiazole...
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Zaporizhzhia State Medical and Pharmaceutical University
2020-08-01
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| Series: | Aktualʹnì Pitannâ Farmacevtičnoï ì Medičnoï Nauki ta Praktiki |
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| Online Access: | http://pharmed.zsmu.edu.ua/article/view/207062/207459 |
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| author | A. S. Hotsulia S. O. Fedotov |
| author_facet | A. S. Hotsulia S. O. Fedotov |
| author_sort | A. S. Hotsulia |
| collection | DOAJ |
| description | Increased attention to thiadiazole and 1,2,4-triazole derivatives is determined by the extensive structural modification capabilities of heterocyclic system derivatives and their high pharmacological potential. Synthesis of new molecules containing, along with the 1,2,4-triazole moiety, thiadiazole is a promising trend in the field of biologically active substances.The purpose of this work was to study the reaction of nucleophilic substitution of 5-((5-amino-1,3,4-thiadiazole-2-ylthio)methyl)-1,2,4-triazole-3-thione with haloalkanes and to establish the structure of the obtained compounds.
Materials and methods. Thiosemicarbazide was used as the key starting reagent. As a result of the reaction of the starting material with carbon disulfide in dimethylformamide, a thione was obtained which was further reacted with the iso-propyl ester of the chloroethane acid. The resulting ester was used for further transformations using hydrazinolysis reaction, nucleophilic addition, and intramolecular alkaline heterocyclization. The alkylderivatives of the obtained 5-((5-amino-1,3,4-thiadiazole-2-ylthio)methyl)-1,2,4-triazole-3-thione were synthesized by reaction with bromoalkanes, in an alcohol medium with an equimolecular amount of alkali. The structure of the synthesized compounds was confirmed by modern physical-chemical methods of analysis: 1H NMR spectroscopy, IR spectrophotometry, and elemental analysis data. The individuality of substances was established by means of high-performance liquid chromatography.
Results. The method of obtaining 5-((5-amino-1,3,4-thiadiazole-2-ylthio)methyl)-1,2,4-triazole-3-thione has been optimized. The optimal conditions for the synthesis S-alkylderivatives of 5-((5-amino-1,3,4-thiadiazole-2-ylthio)methyl)-1,2,4-triazole-3-thione were determined. The structure of the synthesized compounds was established and their physical properties were investigated.
Conclusions. A number of S-alkylderivatives of 5-((5-amino-1,3,4-thiadiazole-2-ylthio)methyl)-1,2,4-triazole-3-thione were obtained and their structure was confirmed by modern physical-chemical methods of analysis |
| format | Article |
| id | doaj-art-bb87796a74ad43f3b27db4d13ac7abb3 |
| institution | Kabale University |
| issn | 2306-8094 2409-2932 |
| language | English |
| publishDate | 2020-08-01 |
| publisher | Zaporizhzhia State Medical and Pharmaceutical University |
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| series | Aktualʹnì Pitannâ Farmacevtičnoï ì Medičnoï Nauki ta Praktiki |
| spelling | doaj-art-bb87796a74ad43f3b27db4d13ac7abb32025-08-20T03:39:10ZengZaporizhzhia State Medical and Pharmaceutical UniversityAktualʹnì Pitannâ Farmacevtičnoï ì Medičnoï Nauki ta Praktiki2306-80942409-29322020-08-0113218218610.14739/2409-2932.2020.2.207062Synthesis and properties of 5-(((5-amino-1,3,4-thiadiazole-2-yl)thio)methyl)-4-phenyl-1,2,4-triazole-3-thione and its some S-derivativesA. S. Hotsulia 0S. O. Fedotov1Zaporizhzhіa State Medical University, UkraineZaporizhzhіa State Medical University, UkraineIncreased attention to thiadiazole and 1,2,4-triazole derivatives is determined by the extensive structural modification capabilities of heterocyclic system derivatives and their high pharmacological potential. Synthesis of new molecules containing, along with the 1,2,4-triazole moiety, thiadiazole is a promising trend in the field of biologically active substances.The purpose of this work was to study the reaction of nucleophilic substitution of 5-((5-amino-1,3,4-thiadiazole-2-ylthio)methyl)-1,2,4-triazole-3-thione with haloalkanes and to establish the structure of the obtained compounds. Materials and methods. Thiosemicarbazide was used as the key starting reagent. As a result of the reaction of the starting material with carbon disulfide in dimethylformamide, a thione was obtained which was further reacted with the iso-propyl ester of the chloroethane acid. The resulting ester was used for further transformations using hydrazinolysis reaction, nucleophilic addition, and intramolecular alkaline heterocyclization. The alkylderivatives of the obtained 5-((5-amino-1,3,4-thiadiazole-2-ylthio)methyl)-1,2,4-triazole-3-thione were synthesized by reaction with bromoalkanes, in an alcohol medium with an equimolecular amount of alkali. The structure of the synthesized compounds was confirmed by modern physical-chemical methods of analysis: 1H NMR spectroscopy, IR spectrophotometry, and elemental analysis data. The individuality of substances was established by means of high-performance liquid chromatography. Results. The method of obtaining 5-((5-amino-1,3,4-thiadiazole-2-ylthio)methyl)-1,2,4-triazole-3-thione has been optimized. The optimal conditions for the synthesis S-alkylderivatives of 5-((5-amino-1,3,4-thiadiazole-2-ylthio)methyl)-1,2,4-triazole-3-thione were determined. The structure of the synthesized compounds was established and their physical properties were investigated. Conclusions. A number of S-alkylderivatives of 5-((5-amino-1,3,4-thiadiazole-2-ylthio)methyl)-1,2,4-triazole-3-thione were obtained and their structure was confirmed by modern physical-chemical methods of analysishttp://pharmed.zsmu.edu.ua/article/view/207062/2074595-aminothiadiazole124-triazolephysical-chemical properties |
| spellingShingle | A. S. Hotsulia S. O. Fedotov Synthesis and properties of 5-(((5-amino-1,3,4-thiadiazole-2-yl)thio)methyl)-4-phenyl-1,2,4-triazole-3-thione and its some S-derivatives Aktualʹnì Pitannâ Farmacevtičnoï ì Medičnoï Nauki ta Praktiki 5-aminothiadiazole 1 2 4-triazole physical-chemical properties |
| title | Synthesis and properties of 5-(((5-amino-1,3,4-thiadiazole-2-yl)thio)methyl)-4-phenyl-1,2,4-triazole-3-thione and its some S-derivatives |
| title_full | Synthesis and properties of 5-(((5-amino-1,3,4-thiadiazole-2-yl)thio)methyl)-4-phenyl-1,2,4-triazole-3-thione and its some S-derivatives |
| title_fullStr | Synthesis and properties of 5-(((5-amino-1,3,4-thiadiazole-2-yl)thio)methyl)-4-phenyl-1,2,4-triazole-3-thione and its some S-derivatives |
| title_full_unstemmed | Synthesis and properties of 5-(((5-amino-1,3,4-thiadiazole-2-yl)thio)methyl)-4-phenyl-1,2,4-triazole-3-thione and its some S-derivatives |
| title_short | Synthesis and properties of 5-(((5-amino-1,3,4-thiadiazole-2-yl)thio)methyl)-4-phenyl-1,2,4-triazole-3-thione and its some S-derivatives |
| title_sort | synthesis and properties of 5 5 amino 1 3 4 thiadiazole 2 yl thio methyl 4 phenyl 1 2 4 triazole 3 thione and its some s derivatives |
| topic | 5-aminothiadiazole 1 2 4-triazole physical-chemical properties |
| url | http://pharmed.zsmu.edu.ua/article/view/207062/207459 |
| work_keys_str_mv | AT ashotsulia synthesisandpropertiesof55amino134thiadiazole2ylthiomethyl4phenyl124triazole3thioneanditssomesderivatives AT sofedotov synthesisandpropertiesof55amino134thiadiazole2ylthiomethyl4phenyl124triazole3thioneanditssomesderivatives |