Synthesis, physical and chemical properties of 2-((4-R-3-(morfolinomethylen)-4H-1,2,4-triazole-5-yl)thio)acetic acid salts

Authors

  • R. О. Shcherbyna Zaporizhzhia State Medical University,

DOI:

https://doi.org/10.14739/2409-2932.2017.1.93424

Keywords:

synthesis, 1, 2, 4-triazoles, physical and chemical properties

Abstract

Today’s medicine and pharmacy undoubtedly need new and effective drugs. The 1,2,4-triazole derivatives occupy a special place among the wide variety of active organic compounds. This interest is caused primarily by high biological activity of these derivatives, low toxicity and high accessibility in terms of synthesis. Thus, drugs from 1,2,4-triazoles are known and are used extensively in medicine. It is important that a sufficiently large number of scientists-synthetics are paying attention on the heterocyclic system. Although a huge amount of information in the scientific literature is devoted to the 1,2,4-triazole derivatives, the 2-((4-R-3-(morfolinometylen)-4H-1,2,4-triazole-5-yl)thio)acetic acid salts are virtually unexplored.

The purpose of the work. Synthesis and establishing of the physical and chemical parameters of new 2-((4-R-3-(morfolinometylen)-4H-1,2,4-triazole-5-yl)thio)acetic acid salts.

Materials and methods. The study of physical and chemical properties of the obtained compounds was conducted by the methods that are listed in the State Pharmacopoeia of Ukraine 2.0. The melting point was defined on the device which determines the melting point MPA100. The elemental composition of the compounds was found on the analyzer Elementar Vario ЕL cube (CHNS) . 1H NMR specters of obtained compounds were recorded by using a spectrometer Varian Mercury VX-200 (1H, 200 MHz) and decrypted by a computer program SpinWorks 3.1.8. Chromatography-mass spectral studies were conducted on the gas-liquid chromatograph Agilent 1260 Infinity HPLC equipped with a mass spectrometer Agilent 6120 (ionization in electrospray (ESI)).

Results and discussion. As the source (starting) compounds 2-((4-R-3-(morfolinometylen)-4H-1,2,4-triazole-5-yl)thio)acetic acids (where, R = H, CH3, C2H5, C6H5, NH2) were taken. Further, by the action of ammonia hydroxide, sodium and potassium hidrogen carbonates, piperidine, morpholine, methylamine, monoethanolamine and tributylamine in alcohol or aqueous media the corresponding salts were obtained.

Conclusions. In this study were synthesized 20 new compounds, salts of 2-((4-R-3-(morfolinometylen)-4H-1,2,4-triazole-5-yl)thio)acetic acid. The structure of the synthesized compounds in all cases was confirmed by modern instrumental methods of analysis (1Н NMR-spectroscopy, chromatography-mass spectrometry and elemental analysis). The synthesized compounds can be used in further biological studies.

References

Danilchenko, D. M., Parchenko, V. V., Panasenko, O. I., & Knysh, Ye. G. (2015). Biolohichni vlastyvosti spoluk, shcho utvoreni poiednanniam 1,2,4-triazolu, furanu ta inshykh funktsionalnykh zamisnykiv [Biological properties of the compounds formed by the combination of the 1,2,4-triazoles, furans and other functional substitutes]. Current issues in pharmacy and medicine: science and practice, 3(19). doi: http://dx.doi.org/10.14739/2409-2932.2015.3.52627. [in Ukrainian].

Pruhlo, Ye. S. (2016). Vplyv 4-benzylidenamino-5-fenil-4N-1,2,4-triazol-3-tioniv i solei 2-(4-amino-5-fenil-4N-1,2,4-triazol-3-iltio)atsetatnykh kyslot na tsentralnyi komponent notsytseptyvnoi systemy [Effect of 4-benzylidenamino-5-phenyl-4Н-1,2,4-triazole-3-thiones and salts of 2-(4-amino-5-phenyl-4Н-1,2,4-triazole-3-ylthio) acetic acid on central component of nociceptive system]. Current issues in pharmacy and medicine: science and practice, 0(2). doi: 10.14739/2409-2932.2016.2.70699. [in Ukrainian].

Parchenko, V.V. (2012). Novi S-pokhidni 1,2,4-tryazolu 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, 43–48. [in Ukrainian].

Kaplaushenko, А. G. (2013). Doslidzhennia zi stvorennia novoho oryhinalnoho vitchyznianoho likarskoho zasobu na osnovi 1,2,4-triazolu [The Research of Creating a New Original Domestic Drug Based on 1,2,4-triazole]. Naukovyi zhurnal MOZ Ukrainy, 2, 115–121. [in Ukrainian].

Parchenko, V. V., Parkhomenko, L. I., Izdepsky, V. Y., Panasenko, O. I., & Knysh, E. G. (2013). Farmakobiokhimichni kharakterystyky piperydynii 2-(5-furan-2-il)-4-fenil-1,2,4-triazol-3-iltioatsetatu [Pharmacological and biochemical characteristics of piperidine 2-(5-furan-2-yl)-4-phenyl-1,2,4-triazol-3-iltioacetate]. Zaporozhye medical journal, 1(76), 39–41. [in Ukrainian].

Pruglo, Y., Pohorlyuk, A., Parchenko, V., Panasenko, A., & Knysh, E. (2016). Antiviral activity of trifuzol for the broiler. Zaporozhye medical journal, 1(94). doi: 10.14739/2310-1210.2016.1.64062. [in Ukrainian].

Sajdov, T. V., & Sverdlova, O. V. (1995). Prakticheskoe rukovodstvo po molekuljarnoj spektroskopii [A Practical Guide to Molecular Spectroscopy]. Saint Peterburg: Izd-vo Sankt-Peterburgskogo universiteta. [in Russian].

Kazitsena, L. A., & Kupletskaya, N. B. (1979). Primenenie UF-, IK-, YaMR - i mass-spektroskopii v organicheskoj khimii [Application of UV, IR, NMR and mass spectrometry in organic chemistry]. Moskow. [in Russian].

Varynskyi, B. O., Knysh, Ye. G., Parchenko, V. V., Panasenko, O. I., & Kaplaushenko, A. G. (2015). Vyvchennia zakonomirnostei utrymuvannia potentsiinykh likarskykh substantsii riadu 1,2,4-tryazol-3-iltioatsetatnykh kyslot ta yikh solei metodom VERKh/DMD-MS [The study of retention regularities for the potential drug substances of 1,2,4-triazol-3-ylthioacetic acids and their salts series by the method of hplc/dad-ms HPLC/DAD-MS]. Zhurnal orhanichnoi ta farmatsevtychnoi khimii, 13(4), 68–75. [in Ukrainian].

Shcherbyna, R. O., Panasenko, O. I., Knysh, Ye. H., & Varynskyy, B. O. (2014). Syntez i fizyko-khimichni vlastyvosti 2-((4-R-3-(morfolinometylen)-4H-1,2,4-triazol-5-il)tio) atsetatnykh kyslot [Synthesis and physical-chemical properties of 2-((4-R-3-(morpholinomethylen)-4H-1,2,4-triazole-5yl)thio)acetic acid]. Current issues in pharmacy and medicine: science and practice, 3, 18–21. [in Ukrainian]. doi: http://dx.doi.org/10.14739/2409-2932.2014.3.30016.

How to Cite

1.
Shcherbyna RО. Synthesis, physical and chemical properties of 2-((4-R-3-(morfolinomethylen)-4H-1,2,4-triazole-5-yl)thio)acetic acid salts. Current issues in pharmacy and medicine: science and practice [Internet]. 2017Feb.20 [cited 2024Jul.21];(1). Available from: http://pharmed.zsmu.edu.ua/article/view/93424

Issue

Section

Synthesis of the biologically active compounds