Synthesis, physical and chemical properties of 3-((5-(hydroxy(phenyl)methine)-4-R-4H-1,2,4-triazole-3-yl)thio)aceto(propane, methylene-о-, m-, p-benzo)nitriles

Authors

  • А. M. Rud Zaporizhzhia State Medical University,
  • A. G. Kaplaushenko Zaporizhzhia State Medical University,
  • Yu. M. Kucheryavyi Zaporizhzhia State Medical University,

DOI:

https://doi.org/10.14739/2409-2932.2016.3.77835

Keywords:

1, 2, 4-triazole, Chemical Synthesis, Chemical Properties, Nitrile Group, HPLC, Mass Spectrometry

Abstract

Cancer is one of the main problems of the whole world. Statistics shows that over the past 100 years the level of morbidity and mortality in the world due to the oncopathologies has moved from tenth to second place. It takes next position only after the diseases of the cardiovascular system. According to WHO data, 10 million people get sick per year. The scientists from WHO have reported that cancer mortality will increase by 45% till 2030 year compared to the level of 2007 year.

Derivatives of 1,2,4-triazole are known among physicians and clinicians of Ukraine and the whole world thanks to its antifungal, antidepressant and especially anticancer properties. Special attention of the doctors and researchers attract drugs such as anastrozole and letrozole. The pharmacological action of these drugs is associated with a combination of the nitrile groups and 1,2,4-triazole core in the molecule structures.

The aim of our research is the development of methods for obtaining new 3-((5-(hydroxy(phenyl)methine)-4-R-4H-1,2,4-triazole-3-yl)thio)aceto(propane, methylene-о-, m-, p-benzo)nitriles, establishing of their structure, physical and chemical properties.

Materials and methods of research. 3-((5-(Hydroxy(phenyl)methine)-4-R-4H-1,2,4-triazole-3-yl)thio)aceto(propane, methylene-о-, m-, p-benzo)nitriles have been obtained by action of corresponding chloronitrile (chloroacetonitrile, 3-chloropropanenitrile or 2-, 3- or 4-(chloromethylene)benzonitriles with (3-thio-4-R-4H-1,2,4-triazole-3-yl)(phenyl)methanols in medium of propanol and equimolar amounts of NaOH. The structure of the obtained compounds has been determined with the modern physical and chemical analysis methods: element analysis, IR-spectrophotometry and their individuality with thin layer chromatography.

Results and their discussion. The synthesis methods have been developed using HPLC-MS research.

Conclusions. We have obtained 13 new compounds. Its structure has been confirmed using modern physical and chemical methods of analysis. We are planning to establish acute toxicity and to study the biological activities of the synthesized compounds at the next stages of research.

References

Mashkovskij, M. D. (1986) Lekarstvennye sredstva [Medications]. Moscow: Medicina. [in Russian].

Shcherbyna, R. O., Panasenko, O. I., Knysh, Ye. H., & Polishchuk, N. M. (2014) Doslidzhennia protymikrobnoi ta protyhrybkovoi aktyvnosti v riadu S-pokhidnykh 3-(morfolinometylen)-4-R-4H-1,2,4-triazol-5-tioliv [Research of antimicrobial and antifungal activity in range of S-derivatives of 3- (morpholinemethylene)-4-R-4H-1,2,4-triazole-5-thiols]. Farmatsevtychnyi zhurnal, 42, 491–495. [in Ukrainian].

Shcherbyna, R. O. (2014) Analiz farmakolohichnoi aktyvnosti pokhidnykh 1,2,4-triazolu [Analysis of the pharmacological activity of 1,2,4-triazole derivatives]. Farmatsevtychnyi chasopys, 4, 145–150. [in Ukrainian].

Shcherbyna, R. O., Pruhlo, Ye. S., Panasenko, O. I., & Knysh, Ye. H. (2014) Poshuk rechovyn z analhetychnoiu diieiu v riadu pokhidnykh 4-R-3-(morfolinometylen)-1,2,4-triazol-5-tiolu [Search for substances with analgesic effect in range of 4-R-3-(morpholinemethylene)-1,2,4-triazoles-5-thiol]. Materiały X międzynarodowej Naukowi-praktycznejkonferencji «Perspektywi czneopracowaniasą nauką itechnikami», (P. 37–38). [in Poland].

Shcherbak, M. O. (2015) Doslidzhennia syntetychnykh, fizyko-khimichnykh i biolohichnykh vlastyvostei 4-amino-5-(2-, 3-, 4-nitrofenil)-1,2,4-triazol-3-tioniv ta yikh N- i S-zamishchenykh (Dis… kand. farm. nauk). [Research of synthetic, physical, chemical and biological properties of 4-amino-5-(2-, 3-, 4-nitrophenyl)-1,2,4-triazole-3-thiones, their N- and S-substituted. Dr. farm. sci. diss.] Zaporіzhzhya. [in Ukrainian].

Sajdov, T. V. (1980) Prakticheskoe rukovodstvo po molekulyarnoj spektroskopii [Practical Guide to Molecular Spectroscopy]. Leningrad: Izd-vo LGU. [in Russian].

Kazicyna, L. A.(1979) Primenenie UF–, IK–, YaMR– i MASS– spektroskopii v organicheskoj khimii [Application of UV, IR, NMR and mass spectroscopy in Organic Chemistry]. Moscow: Izd-vo Mosk. un-ta. [in Russian].

Downloads

How to Cite

1.
Rud АM, Kaplaushenko AG, Kucheryavyi YM. Synthesis, physical and chemical properties of 3-((5-(hydroxy(phenyl)methine)-4-R-4H-1,2,4-triazole-3-yl)thio)aceto(propane, methylene-о-, m-, p-benzo)nitriles. Current issues in pharmacy and medicine: science and practice [Internet]. 2016Sep.22 [cited 2024Nov.24];9(3). Available from: http://pharmed.zsmu.edu.ua/article/view/77835

Issue

No. 3 (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)