Synthesis, physical and chemical properties of esters of 2-((5-(hydroxy(phenyl)methyl)-4-R-1,2,4-triazole-3-yl)thio)ethanoic and 3-(((5-(hydroxy(phenyl)methyl)-4-R-1,2,4-triazole-3-yl)thio)methyl)benzoic acids
DOI:
https://doi.org/10.14739/2409-2932.2017.3.113258Keywords:
1, 2, 4-triazole, synthesis, chemical properties, HPLC-MSAbstract
The wide use of 1,2,4-triazole derivatives in medical practice is primarily explained by two most important properties: high biological activity and low toxicity. It is difficult to overestimate the contribution to medical practice, which such medicines as posaconazole and letrozole have made. Many scientists of the pharmaceutical industry pay attention to the search of biologically active substances among this heterocyclic system derivatives.
Aim. The aim of our study is purposeful synthesis of new highly effective and low-toxic substances among the derivatives of 2-((5-(hydroxy(phenyl)methyl)-4-R-1,2,4-triazol-3-yl)thio)ethanoic and 3-(((5-(hydroxy(phenyl)methyl)-4-R-1,2,4-triazol-3-yl)thio)methyl)benzoic acids, the study of their physical and chemical properties.
Materials and methods. The 2-((5-(hydroxy(phenyl)methyl)-4-R-1,2,4-triazol-3-yl)thio)ethanoic and 3-(((5-(hydroxy(phenyl)methyl)-4-R-1,2,4-triazol-3-yl)thio)methyl) benzoic acids were used as initial substances, which were obtained at the previous stage of synthesis. The esters were synthesized by the esterification of 2-((5-(hydroxy(phenyl)methyl)-4-R-1,2,4-triazol-3-yl)thio)ethanoic and 3-(((5-(hydroxy(phenyl)methyl)-4-R-1,2,4-triazol-3-yl)thio)methyl)benzoic acids in the appropriate alcohol medium with the addition of concentrated sulfuric acid in catalytic amoun.
Results. The structure of obtained compounds was established using a complex of modern physical and chemical analysis methods. The experimental determination of the elemental composition of the obtained substances corresponds to the calculated data. The only one peak was detected on the chromatograms of synthesized esters, which corresponds to the calculated molecular weight m/z+ of series compound. The IR-spectra of the synthesized compounds have the absorption bands of the C-S groups, absorption bands of the aromatic ring, symmetric and asymmetric absorption bands of the C-O-C groups and they fit with reference data. The 1H NMR spectra have proton signals of methyl and methylene groups of the obtained compounds. It ultimately confirms the structure of the synthesized compounds.
Conclusions. We have developed effective laboratory methods for the preparation of esters of 2-((5-(hydroxy(phenyl)methyl)-4-R-1,2,4-triasole-3-yl)thio)ethanoic and 3-(((5-(hydroxy(phenyl)methyl)-4-R-1,2,4-triazol-3-yl)thio)methyl)benzoic acids during the experimental work. Thirteen new compounds were synthesized which are now the objects of further pharmacological researches.
References
Parchenko, V. V. (2014) Syntez, peretvorennia, fіzyko-khіmіchnі ta bіolohіchnі vlastyvostі v riadі 5-furylzamіshchenykh 1,2,4-trіazol-3-tіonіv (Dis… dokt. farm. nauk). [Synthesis, transformation, physical, chemical and biological properties in range of 5-furyl-substituted 1,2,4-triasole-3-thione. Dr. farm. sci. diss.]. Zaporizhzhia. [in Ukrainian].
Parchenko, V. V. (2012) Novi S-pokhidni 1,2,4-triazolu, yak potentsiini oryhinalni vitchyzniani veterynarni likarski zasoby [New S-derivatives of 1,2,4-triazoles as potential original home of veterinary pharmaceuticals]. Farmatsevtychnyi zhurnal, 3, 42–48. [in Ukrainian].
Samelyuk, Y. G., & Kaplaushenko, A. G. (2015) The synthesis and physicochemical properties of 2-(5-methoxy-phenyl-1H-1,2,4-triazole-3-ylthio) acetonitriles and their iminoethers. Zhurnal orhanichnoi ta farmatsevtychnoi khimii, 13, 3(51), 57–62.
Samelyuk, Y. G., & Kaplaushenko, A. G. (2014) Synthesis of 3-alkylthio(sulfo)-1,2,4-triazoles, containing methoxyphenyl substituents at С5 atoms, their antipyretic activity, propensity to adsorption and acute toxicity. J. Chem. Pharm. Res, 6(5), 1117–1121.
Samelyuk, Y. G., Kaplaushenko, A. G., Avramenko, A. I., & Pryakhin, O. R. (2013) The study of acid-base properties of 5-(4-methoxyphenyl, 3,4,5-trimethoxyphenyl)-1,2,4-triazole-3-thioacetic acids and their salts. Intellectual Archive, 2(6), 80–88.
Tarasevich, B. N. (2012) IK spektry osnovnykh klassov organicheskikh soedinenij. Spravochnye materialy [IR spectra of the main classes organic compounds’. Reference materials]. Moscow: MGU. [in Russian].
Kazicyna, L. A. (1979) Primenenie UF-, IK-, YaMR- i MASS-spektroskopii v organicheskoj khimii [Application of UV, IR, NMR and mass spectroscopy in Organic Chemistry]. Moscow: MGU [in Russian].
Nifant'yev, I. E´., & Ivchenko, P. V. (2006) Prakticheskij kurs spektroskopii yadernogo magnitnogo rezonansa [Practical course of nuclear magnetic resonance spectroscopy]. Moscow. [in Russian].
Downloads
How to Cite
Issue
Section
License
Authors who publish with this journal agree to the following terms:
- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
- Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access)
