Synthesis and physical properties of esters of 2-[5-((theophylline-7ʹ-yl)methyl)-4-R-1,2,4-triazole-3-ylthio]acetic acid

Abstract

The large synthetic potential and high biological potential in the series of 1,2,4-triazole derivatives cause favorable conditions for the search for new biologically active substances. A special attention is paid to the possibility of introducing various substituents at the stage of 1,2,4-triazole-3-thiol structure formation. At the same time, derivatives of xanthine are known as the basis for obtaining a wide range of drugs. The aim of this work was the synthesis and properties’ study of new compounds in the series of esters of 2-[5-((theophylline-7ʹ-yl)methyl)-4-R-1,2,4-triazole-3-ylthio]acetic acids. Materials and methods. The strategy of the synthesis of all target products of the reaction was based on the use of theophylline as starting material. To obtain the intermediate thiol we used reactions of esterification, nucleophilic substitution, hydrazinolysis and intermolecular alkaline heterocyclic. The esters of 2-[5-((theophylline-7ʹ-yl)methyl)-4-R-1,2,4-triazole-3-ylthio]acetic acid were obtained by two methods. The melting point was determined using capillary method on OptiMelt MPA 100 (SRS, USA). The structure of the compounds was confirmed with elemental analysis on Elemental Vario EL cube (Elementar Analysensysteme, Germany), IR spectra (4000–400 cm-1) were taken off the module ALPHA-T of Bruker ALPHA FT-IR spectrometer (Bruker optics, Germany). Chromate-mass-spectral studies were carried out on Agilent 1260 Series LC/MSD System. Conclusion. The optimal conditions of obtaining esters of 2-[5-((theophylline-7ʹ-yl)methyl)-4-R-1,2,4-triazole-3-ylthio]acetic acid have been determined. 15 not described previously compounds have been synthesized, its structure has been confirmed by physical and chemical methods of analysis. It has been established that the synthesis of esters of 2-[5-((theophylline-7'-yl)methyl)-4-R-1,2,4-triazole-3-ylthio]acetic acid proceeds with greater yield, if they are gotten directly from the thiol.

Keywords

• triazole
• theophylline
• physical properties
• organic synthesis
• esters