Synthesis and physical-chemical properties of 3-(4-(tert-butyl)phenyl)-5-(R-ylthio)-4H-1,2,4-triazol-4-amines

Authors

  • I. I. Aksyonova Zaporizhzhia State Medical University,
  • O. I. Panasenko Zaporizhzhia State Medical University,
  • Ye. G. Knysh Zaporizhzhia State Medical University,

DOI:

https://doi.org/10.14739/2409-2932.2016.1.62008

Keywords:

Organic Synthesis, Derivatives, Aminotriazole, 1, 2, 4-triazoles

Abstract

Aim. 1,2,4-triazole derivatives are widely used in medical practice due to its wide range of biological effect and small toxicity. This fact makes this class of organic heterocyclic compounds especially interesting and promising for the study of their physical-chemical and biological properties. Thirteen novel compounds, namely 3-(4- (tert-butyl)phenyl)-5-(R-ylthio)-4H-1,2,4-triazole-4-amines, that were not previously described in the literature, have been synthesized with the aim of search for new potentially biologically active compounds.

Methods and results. In order to create new biologically active compounds 13 novel 3-(4-(tert-butyl)phenyl)-5-(R-ylthio)-4H-1,2,4-triazole-4-amines have been synthesized, preparative methods of their synthesis have been proposed, the structure of synthesized compounds has been confirmed by IR-, 1H NMR-spectroscopy, chromatography-mass spectrometry and elemental analysis. In addition, the compounds have been tested for antimicrobial and antioxidative activities.

Conclusions. A preparative methods of synthesis of  3-(4-(tert-butyl)phenyl)-5-(R-ylthio)-4H-1,2,4-triazol-4-amines that can be used for chemical modeling of new biologically active compounds are described. The structure of the synthesized compounds was confirmed by complex of modern methods of investigation, namely: IR-, 1H NMR-spectroscopy, chromatography-mass spectrometry and element analysis.

This indicates the possibility of using these substances to further biological studies.

References

Aksonova, I. I., Panasenko, O. I., Knysh, Ye. H., & Polishchuk, N. M. (2014) Syntez ta protymikrobna aktyvnist pokhidnykh 4-amino-5-(4-tretbutylfenil)-4N-1,2,4-triazol-3-tiolu [Synthesis and antimicrobial activity of derivatives of 4-amino-5-(4-tretbutylfenil)-4H-1,2,4-triazoles-3-thiol]. Farmatsevtychnyi zhurnal, 6, 62–68. [in Ukrainian].

(2004) Derzhavna farmakopeya Ukrayiny [State Pharmacopoeia of Ukraine]. Kharkiv: RIREH. [in Ukrainian].

Tarasevich, B. N. (2012) IK spektry osnovnykh klassov organicheskikh soedinenij. Spravochnye materialy [IR spectra of the major classes of organic compounds. Reference materials]. Moscow: Izd-vo Moskovskogo gosudarstvennogo universiteta imeni M. V. Lomonosova. [in Russian].

Al-Aabdullah, E. S., Asiri, H. H., Lahsasni, S., Habib, E. E., Ibrahim, T. M., & El-Emam, A. A. (2014) Synthesis, antimicrobial, and anti-inflammatory activity, of novel s-substituted and n-substituted 5-(1-adamantyl)-1,2,4-triazole-3-thiols. Drug Design, Development and Therapy, 8, 505–517. doi: 10.2147/DDDT.S62465.

Deng, X.-Q., Song, M.-X., Zheng, Y., & Quan, Z.-S. (2014) Design, synthesis and evaluation of the antidepressant and anticonvulsant activities of triazole-containing quinolinones. European Journal of Medicinal Chemistry, 73, 217–224. doi: 10.1016/j.ejmech.2013.12.014.

Huawen, Huang, Wei, Guo, Wanqing, Wu, Chao-Jun, Li, & Huanfeng, Jiang (2015) Copper-Catalyzed Oxidative C(sp3)–H Functionalization for Facile Synthesis of 1,2,4-Triazoles and 1,3,5-Triazines from Amidines. Organic Letters, 17(12), 2894–2897. doi: 10.1021/acs.orglett.5b00995.

Ledeţi, I., Bercean, V., Alexa, A., Şoica, C., Şuta, L-M., Dehelean, C. et al. (2015) Preparation and Antibacterial Properties of Substituted 1,2,4-Triazoles. Journal of Chemistry. Hindawi Publishing Corporation, 2015, 1–5. http://dx.doi.org/10.1155/2015/879343.

Narayana Rao, D. V., Raghavendra Guru Prasad, A., Spoorthy, Y. N., Raghunatha Rao, D., & Ravindranath, L. K. (2014) Synthesis, characterization and pharmacological studies of sulphur containing 1,2,4-triazole derivatives. Journal of Taibah University Medical Sciences, 9, 293–300. doi:10.1016/j.jtumed.2014.06.002.

Downloads

How to Cite

1.
Aksyonova II, Panasenko OI, Knysh YG. Synthesis and physical-chemical properties of 3-(4-(tert-butyl)phenyl)-5-(R-ylthio)-4H-1,2,4-triazol-4-amines. Current issues in pharmacy and medicine: science and practice [Internet]. 2016Mar.9 [cited 2024Nov.23];(1). Available from: http://pharmed.zsmu.edu.ua/article/view/62008

Issue

No. 1 (2016)

Section

Synthesis of the biologically active compounds

License

Authors who publish with this journal agree to the following terms:

    1. Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.     Лицензия Creative Commons
    2. Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
    3. Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access)