Synthesis of series S-5-R-4-R1-4H-1,2,4-triazol-3-ilsulfonthioates and investigation of their further oxidation
Journal Title: Фармацевтичний журнал - Year 2014, Vol 3, Issue 3
Abstract
hemistry of 1,2,4-triazole attracts both domestic and foreign researchers due to the fact that, based on this heterocycle created substances widely used in various spheres of life . Widely studied synthetic, physical-chemical and biological properties of 1,2,4-triazole-3-thione with various substituents on the heterocyclic structure as well as the sulfur atom but there is no information about studying the reactions of obtaining a series of S-5R-4-R1-4H-1,2,4-triazole-3-ilsulfonthioats and study their further oxidation, which was the goal of our research. It was studied several acylation reactions previously obtained 5-R-4-R1-1,2,4-triazole-3-thiones, using benzenesulfonylchloride as the acylating agent, 4-toluenesulfonyl chloride and metiluratsilsulfohloridafor solution this goal. This reaction has been carried out at room temperature. 5-R-4-R1-1,2,4-triazole-3-thione derivatives have been heated with an equivalent amount of hydroxide and the sulfonyl chlorides was addedas 1,4-dioxane solution (benzensulfonyl, 4-toluensulfonyl chloride), or in crystalline form (using methyluracilsulfchloride) only after cooling the reaction mixture. Substances from S-5-R-4-R1-4H-1,2,4-triazol-3-ilsulfonthyoateshave been oxidized to 5-R-4-R1-3-ilsulfonil-4H-1,2,4-triazole in order to expand the range of pharmacologically active substances. Oxidation reaction has been carried out with pergydrole in a concentrate acetate acid. The structure of the obtained S-5-R-4-R1-4H-1,2,4-triazol-3-ilsulfonothyoatshas been identified by elemental analysis and by infrared spectrophotometry. It was used MS-analysis for confirming the structure of the synthesized substances. Thus, the mass spectrum of S-(5-(4-nitrophenil)-4-phenil-4H-1,2,4-triazol-3-il)benzensulfonothyiate (gross formula C20H14N4O4S2 mol. weight 438 a. m. u.) showed peak M+ with m/z 439. Fragmentation of substance proceedswith detachment ofsulfophenyl fragment and with formation of ion with m/z 297-298. Additionally, it was found SO2-fragment (m/z 64) benzene debris (m/z 77) in mass-spectrum of research compound. The structure of the obtained 5-R-4-R1-3-R1-ilsulfonilsulfonil-4H-1,2,4-triazole confirmed by elemental analysis and by IR-spectrophotometry. It was synthesized 15 new compounds derivatives of 1,2,4-triazole-3-thione, which will become the basis for the study of biological activity.
Authors and Affiliations
A. G. Kaplaushenko
Keywords
Related Articles
- EP ID EP587621
- DOI -
- Views 77
- Downloads 0
Study of component composition of volatile compound of Bidens tripartita herb
The chemical composition of the Bidens tripartita herb has been not studied well. We know that the content of essential oil is 0.11% in the herb but we did not find information about its componential content. Therefore,...
Rationale of method of analysis of evidence-based data on the pharmacological activity of succinic acid and its combinations drugs
Succinic acid as endogenous metabolite has a wide range of applications in medical practice in Ukraine and abroad. We research a new medicines, based on succinic acid, ascorbic acid and rutin for the prevention and treat...
Study of stability elaboration cream Сlotrikarb
Study the establishment of stability and shelf-life of the drug (HP) is one of the important tasks of pharmaceutical development. When a new drug shelf-life is determined experimentally by periodic assessment of quality...
State principles of the medicines circulation regulation around the world and in Ukraine in the pharmacotherapy of orphan diseases among disabled children based on pharmaceutical law
Most rare diseases are serious chronic health problems, many of which accompanied by alarming symptoms that affect the quality and length of life. According to the WHO experts, the number of disabled children in Ukraine...
Analysis of assortment and volumes of consumption of antihistamin preparations in Ukraine
Over the past 30 years, the prevalence of allergic diseases has doubled every 10 years. According to WHO, currently about 5% of the world's adult population and 15% of children suffer from allergic diseases. The purpose...