SYNTHESIS OF NEW BIOLOGICALLY ACTIVE THIETHANE CONTAINING DERIVATIVES OF THIOPYRIMIDINE
Abstract
As a result of this research, synthesis, prediction of biological activity, toxicity of new O -thiethane containing derivatives of 2- thiopyrimidine was carried out.The individuality of the synthesized compounds was confirmed by thin-layer chromatography and the determination of the melting point, the determination of the structure and possible isomers of the obtained compounds was made using the NMR spec-troscopy method.The interaction of ethyl-2-[6-methyl-4-(thiethan-3-yloxy)pyrimidin-2-ylthio]acetate with hydrazine hydrate was studied, a method of the preparation of 2-[6-methyl-4-(thiethan-3-yloxy)pyrimidin-2-ylthio]acetic acid was developed. According to the NMR spectra, the presence of two proton signals of the thioacetohydrazide fragment indicates E,Z -isomerism characteristic for hydrazides due to inhibited rotation around the hydrazide N-C bond.Based on 2-[6-methyl-4-(thiethan-3-yloxy)pyrimidinylthio]acetic acid hydrazide, the corresponding hydrazones were prepared by reaction with carbonyl compounds by boiling in ethanol without the use of acid catalysts.A preliminary prediction of possible types of biological activity for the new synthesized O -thiethane containing derivatives of 2-thiopyrimidine was carried out using computer programs PASS and GUSAR.According to the prediction, the synthesized compounds belong to low-toxic substances and can exhibit antimicrobial, antiviral,nootropic activity, be Maillard reaction inhibitor, thiol protease inhibitor and stimulate leukopoiesis.
About the Author
A. V. Shumadalova
ФГБОУ ВО «Башкирский государственный медицинский университет» Минздрава России
Russian Federation
References
1. Черновьянц, М.С. Хроматографическое определение 6-замещенных 2-тиоурацилов, препаратов тиреостатического действия / М.С. Черновьянц, А.О. Долинкин, И.В. Браславская // Журнал аналитической химии. - 2008. - Т. 63, № 9. - С. 930-934
2. Синтез и биологическая активность производных пиримидина / А.Р. Гимадиева [и др.] // Башкирский химический журнал. - 2007. - Т.14, №3. - С. 5-20
3. Синтез новых серосодержащих ацилпроизводных пиримидина и исследование их влияния на генерацию активных форм кислорода и процессы перекисного окисления липидов in vitro / И.Я. Фаттахова [и др.] // Медицинский вестник Башкортостана. - 2016. - Т. 11, № 5. - С.136-140
4. Синтез, изомерия и гипотензивная активность тиетансодержащих гидразонов урацилилуксусной кислоты / С.А. Мещерякова [и др.] // Биоорганическая химия. - 2014. - T. 40, № 3. - C. 327
5. Fathalla, O.A. Synthesis of new 2-thiouracil-5-sulphonamide derivatives with antibacterial and antifungal activity / O.A. Fathalla, S.M. Awad, M.S. Mohamed // Archives of pharmacal research. - 2005. - Vol. 28, № 11. - P. 1205-1212
For citations:
Shumadalova A.V.
SYNTHESIS OF NEW BIOLOGICALLY ACTIVE THIETHANE CONTAINING DERIVATIVES OF THIOPYRIMIDINE. Bashkortostan Medical Journal. 2017;12(4):59-62.
(In Russ.)
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