Physical-chemical properties of 5-(3-fluorophenyl)-4-amino-1,2,4-triazole-3-thiol s-derivatives

Bihdan, O. A.; Парченко, В. В.

doi:10.14739/2409-2932.2017.2.103517

Cited by 8 publications

(8 citation statements)

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“…1), which were first synthesized in the laboratory of organic synthesis of the Department of Natural Sciences for foreign students and toxicological chemistry of Zaporizhzhia State Medical and Pharmaceutical University. Physical-chemical constants of the synthesized compounds have been studied and described before, some of them are given in the literature [1,10].…”

Section: Methodsmentioning

confidence: 99%

“…The achievements of Ukrainian scientists in the field of synthetic organic chemistry significantly contribute to the development of world science. Among the variety of known organic compounds, the heterocyclic system of 1,2,4-triazole deserves special attention, as it has been at the center of research for decades [1,2,5]. The 1,2,4-triazole cycle has unique properties, which make it a very attractive target for research [3,4].…”

Section: Original Researchmentioning

confidence: 99%

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Diuretic activity of some 4- and 3-thio-substituted 1,2,4-triazoles with fluorophenyl fragments

et al. 2023

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Diuretics increase the volume of urine and sodium excretion, and therefore are often used to remove excess fluid from the body during various diseases, including hypertension, heart and kidney failure, nephrotic syndrome, cirrhosis, etc. Until now, a wide range of diuretics is known, but none of them is completely safe and has a number of side effects. The aim of the work is to investigate the diuretic activity of 1,2,4-triazole derivatives containing fluorophenyl substituents at the fifth position of the 1,2,4-triazole fragment, as well as to establish the relationship between “chemical structure and diuretic action” among derivatives 1,2,4-triazole. Materials and methods. To study the effect on kidney function, six groups of animals with seven rats each were used. When studying water diuresis, rats were kept on a constant diet with free access to water. Before water loading (5 % of body weight), rats were fasted for 2 hours without food and water. Since all tested compounds were insoluble in water, they were administered orally as an aqueous suspension stabilized with Tween-80. The compounds were administered at a dose of 1/10 LD50. Results. The diuretic activity of 28 new compounds of a number of substituted 1,2,4-triazole-3-thiols, which according to their chemical structure belong to different classes of compounds, was investigated. Conclusions. Analysis of the results of diuretic activity indicates that there are a number of compounds whose activity is higher than hypothiazide, as well as a compound that exceeds the activity of furosemide.

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Section: Methodsmentioning

confidence: 99%

Section: Original Researchmentioning

confidence: 99%

Diuretic activity of some 4- and 3-thio-substituted 1,2,4-triazoles with fluorophenyl fragments

et al. 2023

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“…The compounds 1, 2, 3a-f, 4a-f were synthesized on the Department of Natural Sciences for Foreign Students and Toxicological Chemistry of Zaporizhzhia State Medical University, according to a known procedure [12]; the compounds were further used in the investigation of their antimicrobial activity [14,15].…”

Section: Methodsmentioning

confidence: 99%

Synthesis and antimicrobial activity of s-substituted derivatives of 1,2,4-triazol-3-thiol

Karpun

Поліщук

2021

SR: PS

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The aim of the work. 1,2,4-triazole derivatives possess a wide range of pharmacological activity, so they are used for the development of drugs and active pharmaceutical ingredients. Due to the reactivity of 1,2,4-triazoles there are many options for their further structural modification on different reaction centers. Therefore, the aim of the work was to obtain new S-substituted derivatives of 1,2,4-triazole-3-thiols, study physicochemical parameters of the substances synthesized, evaluate the antimicrobial activity of new S-derivatives of the 4-R1-5-((3-(pyridin-4-yl)-1H-1,2,4-triazol-5-yl)thio)methyl)-4H-1,2,4-triazole-3-thiol series, and study some regularities of the “structure – biological activity” relationship for the synthesized compounds as well. Materials and methods. The subject of the study was new S-substituted 1,2,4-triazoles containing 2-oxopropan-1-yl and 2-aryl-2-oxoethan-1-yl substituents. The antimicrobial activity was studied by double serial dilutions on test cultures of Staphylococcus aureus (ATCC 25923), Escherichia coli (ATCC 25922), Pseudomonas aeruginosa (ATCC 27853), and Candida albicans (ATCC 885-653). The results of the biological screening showed that at a concentration of 125 g/mL, all synthesized substances showed activity (MIC – in the range of 31.25 - 62.5 μg/mL, MBCK - in the range of 62.5–125 μg/mL) against strains of Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Candida albicans. Variation of substituents on the sulfur atom did not lead to a significant change in antimicrobial and antifungal activities among derivatives of 4-R1-5-((3-(pyridin-4-yl)-1H-1,2,4-triazole-5-yl) thio)methyl)-4H-1,2,4-triazole-3-thiols. Conclusions. Biological screening data indicate the prospects for the search for new antimicrobial substances among the abovementioned derivatives of 1,2,4-triazoles. The most active compounds were 1-((4-ethyl-5-((3-(pyridin-4-yl)-1H-1,2,4-triazol-5-yl)thio)methyl)-4H-1,2,4-triazol-3-yl)thio)propan-2-one and 1-(4-methoxyphenyl)-2-(4-ethyl-5-(((3-(pyridin-4-yl)-1H)-1,2,4-triazol-5-yl)thio)methyl)-4H-1,2,4-triazol-3-yl)thio)ethanone, which showed the most pronounced antimicrobial activity against the Pseudomonas aeruginosa strain (MIC – 31.25 μg/mL, MBcK - 62.5 μg/mL)

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“…The analysis of this indicator in toxicological studies makes it possible to identify the target organ of the toxicant, to identify signs of endocrine-related effects. The unique properties of 1,2,4-triazole make this heterocycle very attractive for research (Bihdan et al, 2019;Hunchak et al, 2020). Studies have shown the high reactivity and low toxicity of 1,2,4-triazole derivatives and the prospect of their use as potential biologically active compounds.…”

Section: Features Of Experimental Modeling Of Tuberculosismentioning

confidence: 99%

“…The advent of 1,2,4-triazole drugs has revolutionized the treatment of people with invasive and fungal infections (Neofytos, 2010;Haegler et al, 2017;Gotsulia et al, 2018;Zazharskyi et al, 2019). However, keep in mind that drugs with a fragment of triazole can cause various side effects and can sometimes interact with other drugs (Samelyuk & Kaplaushenko, 2015;Fard et al, 2016;Bihdan et al, 2019;Palchykov et al, 2020). Haegler et al (2017) noted that in HepG2 cells (human hepatocarcinoma), posaconazole and ketoconazole were cytotoxic starting at 20 and 50 μM, and decreased cellular ATP content starting at 5 and 10 μM.…”

Section: Introductionmentioning

confidence: 99%

Features of experimental modeling of tuberculosis in guinea pig with the participation of N'-(2-(5-((thephylline-7' yl)methyl)-4-R-1,2,4-triazole- ylthio)acethyl)isonicotinohydrazide

Gotsulya¹,

Zazhzharskiy²,

Давиденко³

2020

Ukr J Ecol

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In this study, no toxic effects were detected after single subcutaneous injection of 40 mg/kg tadpoles. The results of macro- and microscopic examination of the internal organs 14 days after single subcutaneous administration of N'-(2-(5-((thephylline-7'-yl)methyl)-4-ethyl-1,2,4-triazole-3-ylthio)acethyl)isonicotino-hydrazide (GKP-305) at a dose of 20, 40 mg/kg showed the absence of any anatomical and morphological abnormalities in the tissue structures of the tentacles. The calculated value of the drug indicates a high degree of safety GKP-305 and its prospects for veterinary practice as an effective and safe tuberculocidal drug.

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Physical-chemical properties of 5-(3-fluorophenyl)-4-amino-1,2,4-triazole-3-thiol s-derivatives

Cited by 8 publications

References 0 publications

Diuretic activity of some 4- and 3-thio-substituted 1,2,4-triazoles with fluorophenyl fragments

Diuretic activity of some 4- and 3-thio-substituted 1,2,4-triazoles with fluorophenyl fragments

Synthesis and antimicrobial activity of s-substituted derivatives of 1,2,4-triazol-3-thiol

Features of experimental modeling of tuberculosis in guinea pig with the participation of N'-(2-(5-((thephylline-7' yl)methyl)-4-R-1,2,4-triazole- ylthio)acethyl)isonicotinohydrazide

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