The synthesis and physicochemical properties of alkyl-2-(3-thio-5-(1Н-tetrazole-1-yl)methyl-4-R-4Н-1,2,4-triazole-3-yl)ethan(propan,benz)imidates

Authors

  • Yu. S. Frolova Zaporizhzhia State Medical University, Ukraine
  • A. H. Kaplaushenko Zaporizhzhia State Medical University, Ukraine

DOI:

https://doi.org/10.24959/ophcj.18.953

Keywords:

1, 2, 4-triazole, 1Н-tetrazole, synthesis, physical-chemical properties

Abstract

The synthesis of new biologically active compounds that will replace expensive foreign medicines at the pharmaceutical market of Ukraine is one of the most important directions in development of modern pharmacy and medicine. The synthesis, study of physicochemical and biological properties of new compounds containing 1,2,4-triazole and 1H-tetrazole cores are important tasks of modern synthetic chemistry.

Aim. To synthesize new highly efficient and low-toxic substances, namely alkil-2-((5-(1Н-tetrazole-1-yl)methyl-4-R-1,2,4-triazole-3-yl)thio)etan(propan,benz)imidates, and study physicochemical properties of all compounds synthesized.

Results and discussion. Twelve new compounds have been obtained as a result of synthetic transformations, the structure of compounds synthesized has been confirmed by modern complex of physicochemical methods of analysis (IR-spectrophotometry, 1H NMR-spectroscopy, elemental analysis), and their individuality has been proven on an Agilent 1260 Infinity HPLC high-performance liquid chromatograph equipped with an Agilent 6120 mass spectrometer.

Experimental part. As starting materials for the synthesis of alkil-2-((5-(1Н-tetrazole-1-yl)methyl-4-R-1,2,4-triazole-3-yl)thio)etan(propan,benz)imidates the corresponding 2-((5-(1Н-tetrazole-1-yl)methyl-4-R-1,2,4-triazole-3-yl)thio)aceto(propane,benzo)nitriles were used. The synthesis was carried out in the absolute alcohol medium (propanol, butanol, octanol or allyl alcohol) with chloroform.

Conclusions. During synthetic and physicochemical studies the preparative methods for the synthesis of alkil-2-((5-(1Н-tetrazole-1-yl)methyl-4-R-1,2,4-triazole-3-yl)thio)etan(propan,benz)imidates have been developed, the structure of the compounds synthesized has been determined and finally confirmed.

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References

  1. Shcherbina, R. O. (2014). Synthesis, transformation, physical-chemical and biological properties of the 2–(4H–1,2,4–triazole–3–ilthio)acetaldehydes. Extended abstract of candidate’s thesis, 231.
  2. Scherbak, M. O. (2015). Investigation of synthesis, physical–chemical and biological properties of 4–amino–5–(2–,3–,4–nitrophenyl)–1,2,4–triazole–3–thione and their N– and S–substituted. Extended abstract of candidate’s thesis, 210.
  3. Kaplaushenko, A. H. (2009). Ukrainian biopharmaceutical journal, 4 (4), 48–56.
  4. Pruglo, Y. (2018). Synthesis, physical and chemical properties and anxiolytic activity of 2–(4–(R–arylidenamino)–5–methyl–4H–1,2,4–triazole–3–YL)thio)acetic acids and their salts. ScienceRise: Pharmaceutical Science, 3 (13), 19–25. https://doi.org/10.15587/2519-4852.2018.135786
  5. Sameluk, Yu G., Kaplaushenko, A. H., Pruglo, Ye. S. (2014). Synthesis and actoprotective activity of salts of 2–(5–(4–methoxyphenyl–(3,4,5–trimethoxyphenyl)–)–1,2,4–triazole–3–ylthio)acetate acids. Zaporozhye medical journal, 2 (83), 107–111. https://doi.org/10.14739/2310-1210.2014.2.25459
  6. Rud, A. M., Kaplaushenko, A. H., Samelyuk, Yu. G. (2018). Synthesis of new alkylsulfonyl(Sulfinyl)–1,2,4–triazole derivatives based on (3–(Alkylthio)–4–R–1,2,4–thriazole–5–yl)(phenyl)methanol’s. Current Issues in Pharmacy and Medicine: Science and Practice, 1 (26), 23–28. https://doi.org/10.14739/2409-2932.2018.1.123641
  7. Verma, C., Quraishi, M. A., & Singh, A. (2016). 5–Substituted 1H–tetrazoles as effective corrosion inhibitors for mild steel in 1 Mhydrochloric acid. Journal of Taibah University for Science, 10(5), 718–733. https://doi.org/10.1016/j.jtusci.2015.10.005
  8. Sribalan, R., Lavanya, A., Kirubavathi, M., & Padmini, V. (2018). Selective synthesis of ureas and tetrazoles from amides controlled by experimental conditions using conventional and microwave irradiation. Journal of Saudi Chemical Society, 22(2), 198–207. https://doi.org/10.1016/j.jscs.2016.03.004
  9. 9. Derzhavna farmakopeia Ukrainy. (2001). DP «Naukovo–ekspertnyi farmakopeinyi tsentr». (1–edition). Kharkiv: RIREH, 556.
  10. 10. Derzhavna farmakopeia Ukrainy. (2004). DP «Naukovo–ekspertnyi farmakopeinyi tsentr». (1–edition, Vol. 1.). Kharkiv: RIREH, 520.
  11. Sajdov, T. V., Sverdlova, O. V. (1995). Prakticheskoe rukovodstvo po molekuliarnoi spektroskopii. St. Petersburg: SPbGU, 236.
  12. Kazitcyna, L. A., Kupletskaia, N. B. (1979). Primenenie UF–, IK–, PMR– i mass–spektroskopii v organicheskoi khimii.Moscow: Mosk. un–ta, 240.
  13. Tarasevich, B. N. (2012). IK–spektry osnovnykh klassov organicheskikh soedinenii. Spravochnye materialy.Moscow: MGU, 54.
  14. Gunther, H. (2013). NMR Spectroscopy: Basic Principles, Concepts, and Applications in Chemistry. Weinheim: Wiley–VCH, 718.

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Published

2018-12-14

How to Cite

(1)
Frolova, Y. S.; Kaplaushenko, A. H. The Synthesis and Physicochemical Properties of Alkyl-2-(3-Thio-5-(1Н-Tetrazole-1-yl)methyl-4-R-4Н-1,2,4-Triazole-3-yl)ethan(propan,benz)imidates. J. Org. Pharm. Chem. 2018, 16, 11-17.

Issue

Vol. 16 No. 4(64) (2018)

Section

Original Researches

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