Synthesis, physical and chemical properties of 5-(adamantane-1-yl)-4-amino-1,2,4-triazole-3-thiol derivatives
DOI:
https://doi.org/10.14739/2310-1210.2016.6.85540Keywords:
1, 2, 4-triazole, Chemical Synthesis, Chemical PropertiesAbstract
Implementation of new highly efficient drugs in medical practice is one of the most urgent problems of modern pharmaceutical industry. Scientific achievements of heterocyclic compounds’ chemistry clearly show that 1,2,4-triazole system is promising object of such research. It should be also noted that compounds, with adamantane "core" deserve special attention.
The aim of our work was to synthesize new derivatives of 5-(adamantan-1-yl)-4-amino-1,2,4-triazole-3-thiols, and to investigate their physical and chemical properties.
Materials and methods. Chemical names of compounds are given in accordance with IUPAC nomenclature (1979) and the IUPAC recommendations (1993). Study of physical-chemical properties of obtained compounds was carried out in accordance with methods listed in the State Pharmacopia of Ukraine. Melting point was determined on the automatic device for determining the melting temperature Stanford Research Systems OptiMelt MPA100 (manufacturing USA). Elemental composition of new compounds was established on the elemental analyzer Elementar Vario EL cube (CHNS) (standard – sulfanilamide). The data of elemental analysis correspond to the calculated one. 1H NMR spectra of compounds were recorded using spectrometer "Mercury 400". Chromato-mass spectra were recorded on a spectrometer Agilent 6890N/5973N/FID production of Agilent Technologies.
Results. The concept of creating biologically active molecules is first of all directed on combining fragments of different molecules in one. Theoretically, this could lead to the new types of compounds with pharmacological action, and sometimes to the potentiation of existing biological properties. Further actions are focused on the physical and chemical properties study of these compounds. To establish the structure of 5-(adamantan-1-yl)-4-((aryl-, heteryl)ilyden)-amino-1,2,4-triazole-3-thiols we used an integrated approach with the use of modern physical and chemical methods of analysis. Individuality of compounds in each case is confirmed by chromatography. The results of the chromatographic investigations showed that in all cases the constants of pseudo molecular ions peaks of obtained 5-(adamantan-1-yl)-4-((aryl-, heteryl)yliden)amino-1,2,4-triazole-3-thiols coincide with theoretical calculations of molecular masses.
Conclusions. New 5-(adamantan-1-yl)-4-((aryl-, heteryl)yliden)amino-1,2,4-triazole-3-thiols have been synthesized, their structure and individuality has been confirmed by complex of modern physical-chemical methods of analysis. In all cases, the values of the investigated physical-chemical constants coincide with the calculated ones.
References
Parchenko, V. V. (2006) Syntez, fizyko-khimichni ta biolohichni vlastyvosti pokhidnykh 1,2,4-triazol-3-tіоnu, yaki mistiat yadro furanu (Dis…kand. farm. nauk.) [Synthesis, physico-chemical and biological properties of the 1,2,4-triazole-3-thione derivatives which contain furan core. Dr. med. sci. diss]. Kyiv [in Ukrainian].
Parchenko, V. V. (2014) Syntez, peretvorennia, fizyko-khimichni ta biolohichni vlastyvosti v riadi 5-furylzamishchenykh 1,2,4-triazol-3-tіоniv (Dis…dokt. farm. nauk.) [Synthesis, transformation, physico-chemical and biological properties in the number of 5-furylsubstituted 1,2,4-triazole-3-thiones. Dr. med. sci. diss]. Zaporizhzhia [in Ukrainian].
Parchenko, V. V., Parkhomenko, L. I., Izdepsky, V. Y., Panasenko, O. I. & Knysh, E. G. (2013) Farmakobiokhimichni kharakterystyky piperydynii 2-(5-furan-2-іl)-4-fеnіl-1,2,4-triazol-3-іltioatsetatu [Pharmacological and biochemical characteristics of piperidine 2-(5-furan-2-yl)-4-phenyl-1,2,4-triazol-3-iltioacetate]. Zaporozhye medical journal, 1(76), 39–41. [in Ukrainian]. doi: http://dx.doi.org/10.14739/2310-1210.2013.1.15453.
Оdincova, V. М., Goculya, A. S., Knysh, Ye. G. & Panasenko, O. I. (2012) Syntez, fizyko-khimichni vlastyvosti, biolohichna aktyvnist 5-(1-adamantyl)-4-R-1,2,4-triazol-3-tіоniv [Synthesis, physico-chemical properties, biological activity of the 5-(adamantane-1-yl)-4- R-1,2,4-triazole-3-thion derivatives]. Khimichni problemy sohodennia. Proceedings of the 6th All-Ukrainian Scientific Conference. (p. 98).
Parchenko, V. V., Yerokhin, V. Ye., Panasenko, O. I. & Knysh, Ye. G. (2010) Syntez, peretvorennia, fizyko-khimichni vlastyvosti 4-alkil-, aryl- ta 4-aminopokhidnykh 1,2,4-triazol-3-tіоliv iz zalyshkamy fragmentiv furanu [Synthesis, transformation, physico-chemical properties of the 4-alkil-, aril- and 4-aminoderivatives of 1,2,4-triazole-3-thioles with furan’s fragments rests]. Zaporozhye medical journal, 4, 83–87. [in Ukrainian].
Ebtehal Suliman Al Abdullah. (2007) Synthesis and biological testing of new 1-adamantyl derivatives: Submitted in Patrial Fulfillment of the Requirements for the Ph. D. Degree in Pharmaceutical Sciences «Pharmaceutical Chemistry»in the College of Pharmacy, King Saud University. Riyadh, Saudi Arabia.
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