Abstract
Potassium 8-R1-9-R2-10-R3-3-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-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.
Highlights
Native and synthetic quinazoline derivatives are some of the priority objects of investigation in current organic and pharmaceutical chemistry
It is known that the introduction of a thio-group in position 6 of the [1,2,4]triazino[2,3-c]quinazoline system allows the obtainment of compounds with significant cytotoxic action against Photobacterium leiognathi [9, 11,12,13] and antimicrobial action against Staphyloccocus aureus and Aspergillus niger [8,9,10,11,12,13]
As starting compounds we used 6-R-3-(3-R1-4-R2-5-R3-2-aminophenyl)-1,2,4-triazin-5ones (1.1–1.26), which were obtained according to known protocols, namely by nucleophilic cleavage of the pyrimidine fragment in 3-R-8-R1-9-R2-10-R3-2H[1,2,4]triazino[2,3-c]quinazolin-2-ones or hydrazinolysis of 2-aryl-[(3H-quinazolin-4ylidene)hydrazono]acetic acids esters [14]
Summary
Native and synthetic quinazoline derivatives are some of the priority objects of investigation in current organic and pharmaceutical chemistry. It is known that the introduction of a thio-group in position 6 of the [1,2,4]triazino[2,3-c]quinazoline system allows the obtainment of compounds with significant cytotoxic action against Photobacterium leiognathi [9, 11,12,13] and antimicrobial action against Staphyloccocus aureus and Aspergillus niger [8,9,10,11,12,13]. The following structure modification of 6-thio-3-R-2H-[1,2,4]triazino[2,3-c]quinazoline-2-ones by synthesis of. Adhering to the previously developed strategies of the target synthesis of chemotherapeutic agents, we decided to realize further structure modifications of 6-thio-3-R-2H-[1,2,4]triazino[2,3-c]quinazoline-2-ones by the introduction of halogen and methyl substituents in positions 8, 9, and study the antibacterial and antifungal activities of the synthesized compounds
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