Synthesis and physical-chemical properties of 3-alkylthio-5-(quinoline-2-yl, 2-hydroxyquinoline-4-yl)-4-R-2,4-dihydro-3H-1,2,4-triazoles
DOI:
https://doi.org/10.14739/2310-1210.2016.3.76801Keywords:
1, 2, 4-triazole, synthesis, physical-chemical propertiesAbstract
The major social and economic problem of pharmaceutical industry is the search for biologically active substances, which may become the basis of new drugs, competitive with expensive imported drugs. Analysis of literature shows that in recent decades the attention is paid to researches of heterocyclic systems as potential biologically active agents of both domestic and foreign scientists. Particular interest in this regard cause 3-thio derivatives of 1,2,4-triazoles. Despite high number of publications relating to synthesis and biological properties of 1,2,4-triazole derivatives, the structure and physical-chemical properties of these compounds are studied insufficiently. In this regard, the study of synthetic, physical-chemical and biological properties of 3-alkylthio-5-(quinoline-2-yl, 2-hydroxyquinoline-4-yl)-4-R1-2,4-dihydro-3H-1,2,4-triazoles in our point of view is a new, theoretically and practically significant direction.
Purpose - targeted synthesis of new low-toxic and highly effective compounds with potential pharmacological activity in a series of 3-alkylthio-5-(quinoline-2-yl, 2-hydroxyquinoline-4-yl)-4-R-2,4-dihydro-3H-1,2,4-triazoles and the study of physical and chemical properties of the synthesized compounds.
Materials and methods. As starting compounds 5-(quinoline-2-il- 2-hydroxyquinoline-4-yl)-4-R1-3-thio-1,2,4-triazoles have been used. Through further cooperation with halogen alkanes (ethyl bromide, propyl bromide, amyl bromide, octyl bromide, nonyl bromide, decyl bromide, cyclohexyl chloride, benzyl chloride) 3-alkylthio-5-(quinoline-2-yl, 2-hydroxyquinoline-4-yl)-4-R1-2,4-dyhidro-3H-1,2,4-triazoles have been obtained.
Results. 15 New compounds have been received as a result of synthetic transformations, the structure of synthesized compounds has been confirmed by modern complex of physical and chemical methods of analysis (IR-spectrophotometry, 1H NMR-spectroscopy, elemental analysis), and their individuality has been proved by thin layer chromatography.
Conclusions. While synthetic and physical-chemical researches, the preparative methods of synthesis of 3-alkylthio-5-(quinoline-2-yl, 2-hydroxyquinoline-4-yl -4-R-2,4-dihydro-3H-1,2,4-triazoles have been developed, the structure of the synthesized compounds has been installed and finally confirmed.
References
Kaplaushenko, A. G. (2008) Syntez, budova i biolohichna aktyvnist pokhidnykh 4-mono- ta 4,5-dyzamishchenykh 1,2,4-triazol-3-tionu (Dis… dokt. farm nauk). [Synthesis, structure and biological activity of 4-mono- and 4,5-disubstituted 1,2,4-triazole-3-thiones Dr. pharm. sci. diss.]. Zaporіzhzhya. [in Ukrainian].
Kolesnik, Yu. M., Knysh, E. G., Panasenko, O. I. et al. (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-triazoles as potential drugs]. Zaporіzhzhya: Karat. [in Ukrainian].
Derzhavne pidpryiemtsvo «Naukovo-ekspertnyi farmakopeinyi tsentr (2001) Derzhavna Farmakopeia Ukrainy [State Pharmacopoeia of Ukraine]. Kharkiv: RІREG. [in Ukrainian].
Derzhavne pidpryiemtsvo «Naukovo-ekspertnyi farmakopeinyi tsentr (2004) Derzhavna Farmakopeia Ukrainy [State Pharmacopoeia of Ukraine. Addition 1]. Kharkiv: RІREG. [in Ukrainian].
Kazicyna, L. A. (1979) Primenenie UF-, IK-, PMR- i MASS-spektroskopii v organicheskoj khimii [Application of UV, IR, NMR and mass spectrometry in organic chemistry]. Moscow: Izd-vo. Mosk. un-ta. [in Russian].
Downloads
How to Cite
Issue
Section
License
Authors who publish with this journal agree to the following terms:
- 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.
- 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.
- 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)