Synthesis, Characterization and Antimicrobial Evaluation of Substituted 1,2,4-Triazole Thiones Containing Pyrazole Moiety

Prasad, Aluru Guru; Rao, D.V. Narayana; Spoorthy, Yadati Narasimha; Rao, D. Raghunatha; Ravindranath, Lakshmana Rao Krishna Rao

doi:10.4328/jcam.2323

Cited by 6 publications

(5 citation statements)

References 21 publications

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“…Reaction of 4-phenyl-5-(pyridin-3-yl)-1,2,4-triazole-3-thiol ( 92b ) with ethyl bromoacetate gave 1,2,4-triazolthioacetate 225 which on reacting with hydrazine hydrate afforded the desired acetohydrazide 226 . Moreover, the synthesis of various N -substituted-2-(2-((4-phenyl-5-(pyridin-3-yl)-4 H -1,2,4-triazole-3-yl)thio)acetyl)hydrazinecarbothioamides 227a – f was achieved by reacting 226 with isothiocyanates ( Scheme 62 ) [ 88 ].…”

Section: Reactions Of 124-triazolethionesmentioning

confidence: 99%

“…Mechanism describes formation of triazolethiones 79a-e.4-Amino-3-(4-methoxybenzyl)-1H-1,2,4-triazole-5(4H)-thione(88) was synthesized in 75% yield by refluxing of potassium 2-(2-(4-methoxyphenyl)acetyl)-hydrazinecarbodithioate (87) with hydrazine hydrate. Condensation of triazolethione 88 with different substituted aldehydes gave Schiff base derivatives 89a-c in 85-86% yields (Scheme 22)[43].…”

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confidence: 99%

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Chemistry and Biological Activities of 1,2,4-Triazolethiones—Antiviral and Anti-Infective Drugs

et al. 2020

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Mercapto-substituted 1,2,4-triazoles are very interesting compounds as they play an important role in chemopreventive and chemotherapeutic effects on cancer. In recent decades, literature has been enriched with sulfur- and nitrogen-containing heterocycles which are used as a basic nucleus of different heterocyclic compounds with various biological applications in medicine and also occupy a huge part of natural products. Therefore, we shed, herein, more light on the synthesis of this interesting class and its application as a biologically active moiety. They might also be suitable as antiviral and anti-infective drugs.

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Section: Reactions Of 124-triazolethionesmentioning

confidence: 99%

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confidence: 99%

Chemistry and Biological Activities of 1,2,4-Triazolethiones—Antiviral and Anti-Infective Drugs

et al. 2020

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“…Nowadays, microbial infections are resistant to an antibiotic. That's why it is one of the biggest problems, which threaten human health and the quality of life [10,12]. Infectious diseases are one of the main causes of a large number of deaths [4,11,15].…”

Section: актуальные вопросы фармацевтической и медицинской науки и прmentioning

confidence: 99%

Synthesis and properties of 5-(((5-amino-1,3,4-thiadiazole-2-yl)thio)methyl)-4-phenyl-1,2,4-triazole-3-thione and its some S-derivatives

Gotsulya

Fedotov

2020

Current Issues in Pharmacy and Medicine: Science and Practice

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A-research concept and design; B-collection and/or assembly of data; C-data analysis and interpretation; D-writing the article; E-critical revision of the article; F-final approval of the article Increased attention to thiadiazole and 1,2,4-triazole derivatives is determined by the extensive structural modification capabilities of heterocyclic system derivatives and their high pharmacological potential. Synthesis of new molecules containing, along with the 1,2,4-triazole moiety, thiadiazole is a promising trend in the field of biologically active substances. The aim of this work was to study the reaction of nucleophilic substitution of 5-((5-amino-1,3,4-thiadiazole-2-ylthio)methyl)-1,2,4-triazole-3-thione with haloalkanes and to establish the structure of the obtained compounds. Materials and methods. Thiosemicarbazide was used as the key starting reagent. As a result of the reaction of the starting material with carbon disulfide in dimethylformamide, a thione was obtained which was further reacted with the iso-propyl ester of the chloroethane acid. The resulting ester was used for further transformations using hydrazinolysis reaction, nucleophilic addition, and intramolecular alkaline heterocyclization. The alkylderivatives of the obtained 5-((5-amino-1,3,4-thiadiazole-2-ylthio)methyl)-1,2,4triazole-3-thione were synthesized by reaction with bromoalkanes, in an alcohol medium with an equimolecular amount of alkali. The structure of the synthesized compounds was confirmed by modern physical-chemical methods of analysis: 1 H NMR spectroscopy, IR spectrophotometry, and elemental analysis data. The individuality of substances was established by means of high-performance liquid chromatography. Results. The method of obtaining 5-((5-amino-1,3,4-thiadiazole-2-ylthio)methyl)-1,2,4-triazole-3-thione has been optimized. The optimal conditions for the synthesis S-alkylderivatives of 5-((5-amino-1,3,4-thiadiazole-2-ylthio)methyl)-1,2,4-triazole-3-thione were determined. The structure of the synthesized compounds was established and their physical properties were investigated. Conclusions. A number of S-alkylderivatives of 5-((5-amino-1,3,4-thiadiazole-2-ylthio)methyl)-1,2,4-triazole-3-thione were obtained and their structure was confirmed by modern physical-chemical methods of analysis. Синтез і властивості 5-(((5-аміно-1,3,4-тіадіазол-2-іл)тіо)метил)-4-феніл-1,2,4-тріазол-3-тіону та його деяких S-похідних А. С. Гоцуля, C. O. Федотов Увага до похідних тіадіазолу та 1,2,4-тріазолу зумовлена широкими можливостями структурної модифікації похідних цих гетероциклічних систем та їхнім високим фармакологічним потенціалом. Синтез нових молекул, що містять тіадіазол поряд із фрагментом 1,2,4-тріазолу,-перспективний напрям у галузі створення біологічно активних субстанцій. Мета роботи-вивчення реакції нуклеофільного заміщення 5-((5-аміно-1,3,4-тіадіазол-2-ілтіо)метил)-1,2,4-тріазол-3-тіону за участю галогеналканів і встановлення структури одержаних сполук. Матеріали та методи. Як ключовий вихідний реагент використали тіосемікарбазид....

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“…A high probability of finding a pharmacologically valuable substances among 1,2,4-triazoles and the broad possibilities for their chemical modifications are a solid foundation for the search for new synthetic drugs among them [5,6]. Compounds containing 1,2,4-triazole moiety have been demonstrated to have antimicrobial, antitumor, analgesic, hypolipidemic, neuroleptic and other kinds of activities [7][8][9][10][11][12]. Hence, the synthesis of new highly effective antimicrobial medicines containing this heterocyclic fragment is a promising branch in pharmaceutical chemistry investigations.…”

Section: Introductionmentioning

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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Synthesis, Characterization and Antimicrobial Evaluation of Substituted 1,2,4-Triazole Thiones Containing Pyrazole Moiety

Cited by 6 publications

References 21 publications

Chemistry and Biological Activities of 1,2,4-Triazolethiones—Antiviral and Anti-Infective Drugs

Chemistry and Biological Activities of 1,2,4-Triazolethiones—Antiviral and Anti-Infective Drugs

Synthesis and properties of 5-(((5-amino-1,3,4-thiadiazole-2-yl)thio)methyl)-4-phenyl-1,2,4-triazole-3-thione and its some S-derivatives

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

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