Nosulenko Inna S, Voskoboynik Olexii Yu, Berest Galina G, Safronyuk Sergiy L, Kovalenko Sergiy I, Kamyshnyi Oleksandr M, Polishchuk Nataliya M, Sinyak Raisa S, Katsev Andrey V
Department of Organic and Bioorganic Chemistry, Zaporizhzhia State Medical University, Mayakovsky ave., 26, 69035, Zaporizhzhia, Ukraine.
Department of Pharmacognosy, Pharmaceutical chemistry and Technologies, Department of post-graduate education, Zaporizhzhia State Medical University, Mayakovsky ave., 26, 69035, Zaporizhzhia, Ukraine.
Sci Pharm. 2014 Mar 24;82(3):483-500. doi: 10.3797/scipharm.1402-10. Print 2014 Jul-Sep.
Potassium 8-R(1)-9-R(2)-10-R(3)-3-R-2-oxo-2H-[1,2,4]triazino[2,3-c]quinazoline-6-thiolates 2.1-2.26 were synthesized via cyclocondensation of 6-R-3-(3-R(1)-4-R(2)-5-R(3)-aminophenyl)-1,2,4-triazin-5-ones 1.1-1.26 with carbon disulfide, potassium hydroxide, and ethanol or with potassium O-ethyl dithiocarbonate in 2-propanol. The corresponding thiones 3.1-3.26 were obtained by treatment of 2.1-2.26 with hydrochloric acid. It was found that the nature of the substituents in positions 3, 4, and 5 of the corresponding 6-R-3-(3-R(1)-4-R(2)-5-R(3)-aminophenyl)-1,2,4-triazin-5-ones were affected on the terms of the reaction. The structures of compounds were proven by a complex of physicochemical methods ((1)H, (13)C NMR, LC-MS, and EI-MS). The results of the antibacterial and antifungal activity assay allowed the determination of the high sensitivity of Staphylococcus aureus ATCC 25923 (MIC 6.25-100 μg/mL, MBC 12.5-200 μg/mL) to the synthesized compounds.
通过6-R-3-(3-R(1)-4-R(2)-5-R(3)-氨基苯基)-1,2,4-三嗪-5-酮1.1-1.26与二硫化碳、氢氧化钾和乙醇或与O-乙基二硫代碳酸钾在2-丙醇中进行环缩合反应，合成了钾8-R(1)-9-R(2)-10-R(3)-3-R-2-氧代-2H-[1,2,4]三嗪并[2,3-c]喹唑啉-6-硫醇盐2.1-2.26。用盐酸处理2.1-2.26得到相应的硫酮3.1-3.26。发现相应的6-R-3-(3-R(1)-4-R(2)-5-R(3)-氨基苯基)-1,2,4-三嗪-5-酮3、4和5位取代基的性质对反应条件有影响。通过多种物理化学方法((1)H、(13)C NMR、LC-MS和EI-MS)对化合物结构进行了确证。抗菌和抗真菌活性测定结果表明，金黄色葡萄球菌ATCC 25923对合成化合物具有高敏感性(MIC 6.25-100μg/mL，MBC 12.5-200μg/mL)。
