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...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
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Zaporozhye State Medical University
2020-08-01
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| Series: | Aktualʹnì Pitannâ Farmacevtičnoï ì Medičnoï Nauki ta Praktiki |
| Subjects: | |
| Online Access: | http://pharmed.zsmu.edu.ua/article/view/207062/207459 |
| Summary: | 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 |
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| ISSN: | 2306-8094 2409-2932 |