Synthesis and antimicrobial activity of 6-Thioxo-6,7-dihydro-2H-[1,2,4]triazino [2,3-c]- quinazolin-2-one derivatives

Abstract

Potassium 8-R1-9-R2-10-R3-3-R-2-oxo-2Н-[1,2,4]triazino [2,3-с]quinazoline-6- thiolates 2.1-2.26 were synthesized via cyclocondensation of 6-R-3-(3-R1-4-R2- 5-R3-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-R1-4-R2-5-R3-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 (1H,13C 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.