Synthesis, physical and chemical properties of 2-((5-(hydroxy(phenyl)methyl)-4R-4H-1,2,4-triazole-3-yl)thio)acetic acids and its salts

Abstract

Today’s a creation of new domestic medicines is very important problem for pharmacy and medicine. Therefore, it is relevant to synthesize new domestic biologically active compounds. It is known that a large number of new 3-thio and 4-amino derivatives on the basis of 1,2,4-triazole have recently been synthesized, among which compounds with high pharmacological activity have been found. Based on the experience of previous studies and with the aim of creating new original drugs, our goal was to synthesize 2-((5-(hydroxy(phenyl)methyl)-4-R-4H-1,2,4-triazole-3-yl)thio)acetic acids series and to obtain salts on its basis, which have high indicators of pharmacological activity based on the literature data. The goal of the work is a targeted synthesis of potential low-toxic and highly effective compounds with a wide spectrum of pharmacological activity among 5-(hydroxy(phenyl)methyl)-4-R-4H-1,2,4-triazole-3-thione derivatives, confirmation of their individuality and structure, as well as the study of physical-chemical properties, for the further pharmacological screening. Materials and methods. 2-((5-(hydroxy(phenyl)methyl)-4-R-4H-1,2,4-triazole-3-yl)thio)acetic acids were prepared by heating 5- (hydroxy(phenyl)methyl)-4-R-4H-1,2,4-triazol-3-thiones with chloroacetic acid. Subsequently, the synthesized thioacetic acids were subject for modification. Salts of 2-((5-(hydroxy(phenyl)methyl)-4-R-4H-1,2,4-triazole-3-yl)thio)acetic acids were obtained by reacting thioacetic acids with equivalents of sodium or potassium hydroxides. To obtain Iron(II), Copper(II) or Zinc(II) salts, half-molar amounts of the appropriate sulfates were added to the obtained solutions. Salts of 2-((5-(hydroxy(phenyl)methyl)-4-R-4H-1,2,4-triazole-3-yl)thio)acetic acids with organic bases were obtained by the reaction of acids with piperidine or morpholine in ethanol medium. Results. During the synthetic studies, 13 previously undescribed new compounds were obtained. The individuality of 2-((5-(hydroxy(phenyl)methyl)-4-R-4H-1,2,4-triazole-3-yl)thio)acetic acids and its salts after recrystallization was confirmed by thin layer chromatography. The structure of synthesized compounds was confirmed by the integrated use of elemental analysis and IR- spectrophotometry. Conclusions. The results of the work confirm the structure of the synthesized compounds, which shows the possibility of further biological investigation.

Keywords

• 4-triazole
• synthesis
• physical properties
• chemical properties