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-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.

25-OH Vitamin D blood serum linkage with VDR gene polymorphism (rs2228570) in thyroid pathology patients in the West-Ukrainian population

“…One of the main directions of biomedical research today is identifying genetic factors and their role in developing multifactorial diseases [ 14 ]. Analysis of the genome can be used to detect these hereditary factors [ 15 , 16 ]; often, mutations contributing to the increased disease risk are single nucleotide polymorphisms [ 17 – 19 ].…”

Synthesis and antimicrobial activity of [1,2,4]triazіno[2,3-c]quinazoline – pyrazoline hybrids

“…Compounds 2.1-2.12 were synthesized by alkylation of potassium thiolates 1 [16] with corresponding 1-(chloroacetyl)-3-aryl(heteryl)-5-aryl-4,5-dihydro-1H-pyrazoles (Figure 2). The last ones were obtained according to the described approaches via series of chemical transformations that included condensation of methylaryl(heteryl)ketones with aromatic aldehydes that yielded chalcones, synthesis of 3-aryl(heteryl)-5aryl-4,5-dihydro-1H-pyrazoles by reaction of the obtained chalcones with hydrazine hydrate and acylation of abovementioned compounds by chloroacetyl chloride [9].…”

“…LC-MS spectra were registered by chromatography/mass spectrometric system that consists of high performance liquid chromatograph Agilent 1100 Series (Agilent, Palo Alto, CA, USA) equipped with diode-matrix and mass-selective detector Agilent LC/MSD SL (atmospheric pressure chemical ionization). Compounds 1 and 1-(chloroacetyl)-3-aryl(heteryl)-5-aryl-4,5-dihydro-1H-pyrazoles were obtained according to the described synthetic protocols [9,16]. The other starting reagents and solvents were obtained from commercially available sources and were used without further purification.…”

“…In view of reasonability of abovementioned way for formation of bioactive molecules and reported by our group data about high antibacterial and antifungal activity of [1,2,4]triazіno [2,3-c]quinazolines [15,16] it was decided to synthesize [1,2,4]triazіno [2,3-c]quinazoline -pyrazoline hybrids and evaluate their antimicrobial effects.…”

Glucocorticoid-induced Changes in the Transcriptional Activity of Genes of the Innate and Adaptive Immune System in the Blood of Patients with Acute Urticaria

“…Determination of the level of gene transcriptional activity is an essential index of the functional activity of cells [9], [10], [11], [12], [13]. Our previous studies show significant changes in the transcriptional profile and genetic variations in different pathological conditions [14], [15], [16], [17], [18], [19]. Changes in some genes expression of the innate and adaptive immune system play a vital role in the mechanisms of AU development.…”