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Sci. Pharm. 2014, 82(3), 483-500; doi:10.3797/scipharm.1402-10 (registering DOI)

Synthesis and Antimicrobial Activity of 6-Thioxo-6,7-dihydro-2H-[1,2,4]triazino[2,3-c]-quinazolin-2-one Derivatives

1
Department of Organic and Bioorganic Chemistry, Zaporizhzhia State Medical University, Mayakovsky ave., 26, 69035, Zaporizhzhia, Ukraine
2
Department of Pharmacognosy, Pharmaceutical chemistry and Technologies, Department of post-graduate education, Zaporizhzhia State Medical University, Mayakovsky ave., 26, 69035, Zaporizhzhia, Ukraine
3
Department of Pharmacy, Crimean State Medical University, 95006, Simferopol, Ukraine
4
Department of Microbiology, Virology and Immunology, Zaporizhzhia State Medical University, Mayakovsky ave., 26, 69035, Zaporizhzhia, Ukraine
5
Department of General Chemistry, Crimean State Medical University, 95006, Simferopol, Ukraine
*
Author to whom correspondence should be addressed.
Received: 17 February 2014 / Accepted: 24 March 2014 / Published: 24 March 2014
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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-amino-phenyl)-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.
Keywords: Synthesis; Potassium salt; 6-Thioxo-6,7-dihydro-2H-[1,2,4]triazino[2,3-c]quinazolin-2-one derivatives; Antimicrobial activity Synthesis; Potassium salt; 6-Thioxo-6,7-dihydro-2H-[1,2,4]triazino[2,3-c]quinazolin-2-one derivatives; Antimicrobial activity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

NOSULENKO, I.S.; VOSKOBOYNIK, O.Y.; BEREST, G.G.; SAFRONYUK, S.L.; KOVALENKO, S.I.; KAMYSHNYI, O.M.; POLISHCHUK, N.M.; SINYAK, R.S.; KATSEV, A.V. Synthesis and Antimicrobial Activity of 6-Thioxo-6,7-dihydro-2H-[1,2,4]triazino[2,3-c]-quinazolin-2-one Derivatives. Sci. Pharm. 2014, 82, 483-500.

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