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

Authors

  • A. M. Rud Zaporizhzhia State Medical University, Ukraine,
  • A. G. Kaplaushenko Zaporizhzhia State Medical University, Ukraine,
  • Yu. G. Samеliuk Zaporizhzhia State Medical University, Ukraine,

DOI:

https://doi.org/10.14739/2409-2932.2018.1.123641

Keywords:

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

Abstract

In recent years, much attention has been paid to the search and creation of new drugs. Purposeful synthesis of compounds with low toxicity and pronounced biological properties is the main stage in the development of medicinal products. Of particular interest in this direction are nitrogen-containing heterocycles, as highly effective pharmacologically active compounds. Great importance in this direction is given to the study of the biological activity of 1,2,4-triazoles, since the 1,2,4-triazole nucleus is a structural fragment of drugs with variety pharmacological effects.

The purpose of our work was to synthesize new compounds in the series of 1,2,4-triazole-3-thione containing hydroxyphenyl substituents, namely synthesise starting compounds, carry out the reactions of alkylation, and study directly oxidation of the Sulfur atom to IV and VI valence states.

Materials and methods. The structure of the synthesized compounds, their identity and purity has been proved by elemental analysis, IR-, UV-spectrophotometry, NMR-spectrometry, TLC, HPLC-MS.

Results. We obtained a number of 1,2,4-triazole-3-thione derivatives, namely, oxidized forms of s-alkyl derivatives, which have practical significance for drug developers, as well as for scientists in the field of organic synthesis. For the obtained compounds it is planned to study acute toxicity, antifungal, antimicrobial, neuroleptic, diuretic, anti-inflammatory, antioxidant, hypolipidemic activity.

But the pharmacological activity of 1,2,4-triazole-3-thione has not been studied sufficiently. From our point of view, the synthesis, study of physical-chemical and biological properties of 1,2,4-triazole-3-thione with hydroxyphenyl substituents have a scientific novelty, theoretical and practical significance. Therefore, the further search for biologically active substances in this series of compounds continues.

Conclusions. The thirteen new biological active compounds (3-(alkylsulfonyl(sulfinyl))-4-R-1,2,4-triazole-5-il)(phenyl)methanols have been synthesized. Their structure has been confirmed using modern methods of analysis.

References

Kolesnyk, Yu. M., Kaplaushenko, A. H., Knysh, Ye. H., Panasenko, O. I., Shcherbak, M. O., & Sameliuk, Yu. H. (2014) Pokhidni 4-amino ta 3-tio-1,2,4-triazolu yak potentsiini likarski zasoby [Derivatives of 4-amino and 3-thio-1,2,4-triazole as potential therapeutics]. Zaporizhzhia. [in Ukrainian].

Shcherbak, M. O., Belenichev, I. F., Abramov, A. V., Bukhtiyarova, N. V., Morguntsova, S. A., Pavlov, S. V., & Kaplaushenko, A. G. (2014) Doslidzhennia kardioprotektornoi aktyvnosti 3-(4-nitrofenil)-5-(nonilsulfonil)-1,2,4-triazol-4-aminu [The research of cardioprotective activity of 3-(4-nitrophenyl)-5-(nonylsulfonyl)-1,2,4-triazole-4-amine]. Farmakolohiia ta likarska toksykolohiia, 3, 64–69. [in Ukrainian].

Gündoğdu-Karaburun, N., Benkli, K., Tunali, Y., Uçucu, U., & Demirayak, S. (2006) Synthesis and antifungal activities of some aryl [3-(imidazol-1-yl/triazol-1-ylmethyl) benzofuran-2-yl] ketoximes. Eur. J. Med. Chem., 41(5), 651–656. doi: 10.1016/j.ejmech.2005.12.013.

Sameliuk, Yu. H., Shcherbak, M. O., & Kucheriavyi, Yu. M. (2013) Doslidzhennia syntetychnykh, fizyko-khimichnykh ta biolohichnykh vlastyvostei pokhidnykh 1,2,4-triazol-3-tioliv [Investigation of synthetic, physical, chemical and biological properties of derivatives of 1,2,4-triazole-3-thiols]. Vitchyzniana ta svitova medytsyna: vymohy sohodennia, (P. 104–105). Zaporizhzhia. [in Ukrainian].

Kucheriavyi, Yu. M., & Kaplaushenko, A. H. (2014) Syntez ta fizyko-khimichni vlastyvosti 5-R-4-R1-1H-1,2,4-triazol-3-tioniv [Synthesis and Physico-Chemical Properties of 5-R-4-R1-1H-1,2,4-Triazol-3-Thione]. Farmakom, 1, 82–86. [in Ukrainian].

Kaplaushenko, A. H. (2005) Syntez, fizyko-khimichni ta biolohichni vlastyvosti S-pokhidnykh 5-(2-, 3-, 4-nitrofenil)-1,2,4-tryazol-3-tioniv (Dis…kand. farm. nauk) [Synthesis, physical, chemical and biological properties of S-derivatives of 5- (2-, 3-, 4-nitrophenyl) -1,2,4-triazole-3-thione. Dr. farm. sci. diss.]. Zaporizhzhia. [in Ukrainian].

Kucheryavyi, Y. M., Kaplaushenko, A. G., & Korzhova, A. S. (2014) Synthesis of 5-R-4-R1-3-alkylthio-1,2,4-triazoles and study influence of their adsorption ability on the results of toxicity and anti-hypoxic activity. The Pharma Innovation, 1, 69–73.

Tarasevich, B. N. (2012) IK spektry osnovnykh klassov organicheskikh soedinenij. Spravochnye materialy [IR spectra of the main classes of organic compounds. Reference materials]. Moscow: MHU. [in Russian].

How to Cite

1.
Rud AM, Kaplaushenko AG, Samеliuk YG. 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 [Internet]. 2018Feb.16 [cited 2024Dec.27];(1). Available from: http://pharmed.zsmu.edu.ua/article/view/123641

Issue

Section

Synthesis of the biologically active compounds