Synthesis, physic and chemical properties of 2-(4-R-5-(thiophene-2-ylmethyl)-4h-1,2,4-triazole-3-ylthio)acetate acids and their salts
Derivatives of 1,2,4-triazole are inherent in various types of biological activity. They can be used as pesticide and medicinal drugs (anticonvulsants, analgetics, antitumor and antibacterial). In this regard the search of new methods of synthesis and investigation of biological activity of 2-(4-R-5-(thiophene-2-ylmethyl)-4H-1,2,4-triazole-3-ylthio)acetate acids and their salts is relevant nowadays.
With the aim of finding the new biologically active compounds 2-(4-R-5-(thiophene-2-ylmethyl)-4H-1,2,4-triazole-3-ylthio)acetate acids and their salts are synthesized, where R is methyl, ethyl, phenyl. The interaction of 4-R-5-(thiophene-2-ylmethyl)-4H-1,2,4-triazole-3-thions with monochloracetate acid in the medium of i-propyl alcohol in the presence of an equivalent amount of alkali the corresponding 2-(4-R-5-(thiophene-2-ylmethyl)-4H-1,2,4 triazole-3-ylthio)acetate acids are obtained on the basis of which the corresponding salts of morpholine, dimethylamine, monoethanolamine, pteridine, ZnSO4 , CuSO4, NaOH and KOH are obtained and the structure of the received compounds was confirmed on the basis of the data of elemental, IR-, 1H-NMR-spectroscopy.
The synthesis of 2-(4-R-5-(thiophene-2-ylmethyl)-4H-1,2,4-triazole-3-ylthio) acetate acids and their salts was conducted. With the help of modern physico-chemical methods: elemental analysis, IR, 1H-NMR-spectroscopy the structure of synthesized compounds, and their individuality by HPLC-MS is proved.
In the IR spectrum of the compound 2-(4-phenyl-5-(thiophene-2-ylmethyl)-4H-1,2,4-triazole-3-ylthio)acetate acid Ic available band fluctuations groups characteristic for the nucleus of 1,2,4-triazole: NH– in the range of 3 400–3 100 cm-1,–C=N– – 1 690–1 620 cm-1. Also present band fluctuations groups –C–S– at 691 cm-1. Available band fluctuations characteristic of the group –CH2 within 1496.59 cm-1 and group –COO-H– – 1722.70 cm-1.
This suggests the possibility to further study the biological action of the synthesized compounds.
2. Iradian MA, et al. Synthesis and antibacterial activity of 3,6-diaryl-7H- [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazines // Chemico-pharmacist . journ - 2016. - Vol. 50, No. 1. - P. 12-16.
3. Kazitsina L. A. Application of UV, IR, NMR and MASS spectroscopy in organic chemistry. 2 ed., Pererab. and add - Moscow: Izv. Mosk. Un-ta, 1979.-236 p.
4. Pruglo Ye.S., Odintsova V. M., Safonov A. A. The anti-hyperactivity of the new hydrazides 2- (5- (adamantan-1-yl) -4-R-1,2,4-triazol-3- iltio) acetates // Farmats. a magazine - 2013. - No. 3. - P. 45-49.
5. Shepeta Yu. L., Lelyukh M. I., Zimenkovsky B. S., Lesik R. B. Synthesis of new derivatives of 4H-1,2,4-triazole-3-thiol from 2- (2,6-dichlorophenylamino ) benzyl fragment in molecules and their anti-inflammatory activity // Act. question of pharmacy. honey. science and practice. - 2016 - No. 1 (20). - P. 18-25.
6. Ding Y., Zhang Z., Zhang G. et al. Green synthesis and evaluation of the antitumor activity of a novel series of 3- [4-bi- (4-fluorophenyl) methylpiperazinyl] -4-amino-5-thione-1,2,4-triazole Schiff bases // Res. Chem Intermed - 2016. - V. 42, Issue 4. - P. 3105-3116.
7. Walaa S. El-Serwy, Neama A. Mohamed, Eman M. Abbas, Rehab F. Abdel-Rahman. Synthesis and anti-inflammatory properties of novel 1,2,4-triazole derivatives // Ibid. - 2013. - V. 39, Issue 6. - R. 2543-2554.
Copyright (c) 2017 Farmatsevtychnyi zhurnal
This work is licensed under a Creative Commons Attribution 4.0 International License.