Synthesis, physico-chemical properties of 2-((4-amino-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazol-3-yl)thio)acetohyd-razides

  • A. A. Safonov Zaporizhzhia State Medical University
Keywords: 1,2,4-triazole, 1H-NMR

Abstract

The value of the class of 1,2,4-triazole derivatives to create a low-toxic and highly active substances is huge. There are a lot of facts about the high biological activity among a number of substances. The 2-((4-amino-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazol-3-yl)thio)acetohydrazides derivatives causes of particular interest in this direction.

The aim of the work was to synthesize 2-((4-amino-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazol-3-yl)thio)acetohydrazides and their derivatives, studying of their physico-chemical properties.

2-((4-amino-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazol-3-yl)thio)-N'-R-acetohydrazides were synthesized by of 2-((4-amino-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazol-3-yl)thio)acetohydrazides with aldehydes and ketones in the i-propanol with the addition of hydrochloric acid.

The melting point was determined by an automatic device for determining the melting point OptiMelt Stanford Research Systems MPA100 (US). The elemental composition of compounds found in elemental analyzer Elementar Vario L cube (CHNS) (standard ‒ sulfonamides). Chromatography-mass spectral studies conducted on gas-liquid chromatograph Agilent 1260 Infinity HPLC with equipped mass spectrometer Agilent 6120, 1H-NMR-spectra were registered on spectrometer Mercury 400

A series of new 2-((4-amino-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazol-3-yl)thio)-N'-R-acetohydrazides derivatives were synthesized, R-2-chloro-6-fluorobenzylidene, 3-nitrobenzylidene, 4-hydroxybenzylidene, 2-nitrobenzylidene, 2,4-dimethylbenzylidene, 3,5-dimethoxybenzylidene, 3-bromo-4-fluorobenzylidene, 2,3-dimethoxybenzylidene, 2-bromobenzylidene, 2-fluorobenzylidene, 4-(dimethylamino)benzylidene, pyridin-2-ylmethylene, 5-nitrofuran-2-ylmethylene, 4-methoxybenzylidene, 2-hydroxybenzylidene, 4-methoxyphenyl)ethylidene, 1-(thiophen-2-yl)ethylidene. The structure of these compounds was established by modern physico-chemical analysis methods (elemental analysis, 1H-NMR spectroscopy). Individuality was proved by HPLC-MS.

References

1. Shcherbyna R. O., Panasenko O. I., Knysh Y. G. Study of antioxidant activity of salts of 2 - ((4-R-3- (morpholinomethylene) -4H-1,2,4-triazol-5-yl ) thio) acetate acids // Ukr. biopharmac. journ - 2016. - № 1. - P. 37-40.
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. Gorshkov VA, et al. An experimental substantiation of the use of certain antioxidants for the treatment of toxic hepatitis in pregnant women // Health and education in the XXI century. - 2016. - Vol. 18, No. 1.
4. Odintsova VN Analgesic activity of 2- (5- (adamantan-1-yl) -4R-1,2,4-triazole-3-ylthio) acetic acid salts // Ac. question of pharmacy. honey. science and practice. - 2016 - No. 1 (20).
5. Bilay I. M., et al. The anaesthetic activity of derivatives of 1,2,4-triazole at the stage of primary pharmacological screening // Pharmacology and drug toxicology. - 2016. - № 1. - P. 48.
6. Gotsulya A. S., et al. Investigation of antimicrobial and antifungal activity of S-derivatives of 7 - ((3-thio-4-R-4H-1,2,4-triazol-3-yl) methyl) theophylline // Zaporozhye . honey. journ - 2015. - No. 4.
7. 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.
Published
2018-08-14
How to Cite
Safonov, A. A. (2018). Synthesis, physico-chemical properties of 2-((4-amino-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazol-3-yl)thio)acetohyd-razides. Farmatsevtychnyi Zhurnal, (5), 31-36. https://doi.org/10.32352/0367-3057.5.16.03
Section
Synthesis and analysis of biologically active compounds