Synthesis, physical-chemical properties and further transformation of 5-(quinoline-2-yl, 2-hydroxyquinoline-4-yl)-4-R-2,4-dyhydro-3Н-1,2,4-triazole-3-thiones

Kaplaushenko, T. M.

doi:10.14739/2409-2932.2016.2.71083

Cited by 3 publications

(10 citation statements)

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“…The structure of synthesized compounds (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15) was confirmed by the complex using of elemental analysis ( Table 2) and IR-spectrophotometry ( Table 3). The elemental composition of the compounds corresponds within the limits of the calculated data error ( Table 2).…”

Section: Resultsmentioning

confidence: 82%

“…There are absorption bands -C=N groups at 1610-1573 cm -1 , -OH groups at 3530-3488 cm -1 , -C-S groups at 707-620 cm -1 , and also absorption of aromatic ring bands at 1501-1470 cm -1 in the IR-spectra of all synthesized compounds. IR-spectra of acids (3,4) additionally contain absorption bands of -CH 2 -COOH groups at 1710-1700 cm -1 , and spectra of salts (5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15) contain bands that are inherent to COO-groups in the range of 1407-1300 cm -1 and at 1595-1536 cm -1 , respectively [13].…”

Section: Resultsmentioning

confidence: 99%

“…1) were obtained by the reaction of 2-((5-(hydroxy(phenyl) methyl)-4-R-4H-1,2,4-triazole-3-yl)thio)acetic acids (3,4) with sodium or potassium hydroxide equivalents. Iron (II), Copper (II), and Zinc (II) 2-((5-(hydroxy(phenyl)methyl)-4-phenyl-4H-1,2,4-triazole-3-yl)thio acetate (11)(12)(13)Fig.…”

Section: Materials and Methods Of Researchmentioning

confidence: 99%

“…Salts of 2-((5-(hydroxy(phenyl)methyl)-4-R-4H-1,2,4-triazole-3-yl)thio)acetic acids with organic bases (7,14,15;Fig. 1) were obtained by reaction of acids (3,4) with piperidine or morpholine. In this case, the reaction medium was ethanol.…”

Section: Materials and Methods Of Researchmentioning

confidence: 99%

“…Publications of recent years [1][2][3][4][5][6] show that the heterocycle with the 1,2,4-triazole nucleus was proven to be well-established as a broad spectrum of biologically active compounds. This fact points to the interest in these compounds as potential objects of the modern pharmaceutical market, namely, compounds that contain both heterocycles.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, physical and chemical properties of 2-((5-(hydroxy(phenyl)methyl)-4R-4H-1,2,4-triazole-3-yl)thio)acetic acids and its salts

Rud

Kaplaushenko

Yurchenko

2018

ZMJ

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Today's a creation of new domestic medicines is very important problem for pharmacy and medicine. Therefore, it is relevant to synthesize new domestic biologically active compounds. It is known that a large number of new 3-thio and 4-amino derivatives on the basis of 1,2,4-triazole have recently been synthesized, among which compounds with high pharmacological activity have been found. Based on the experience of previous studies and with the aim of creating new original drugs, our goal was to synthesize 2-((5-(hydroxy(phenyl)methyl)-4-R-4H-1,2,4-triazole-3-yl)thio)acetic acids series and to obtain salts on its basis, which have high indicators of pharmacological activity based on the literature data.The goal of the work is a targeted synthesis of potential low-toxic and highly effective compounds with a wide spectrum of pharmacological activity among 5-(hydroxy(phenyl)methyl)-4-R-4H-1,2,4-triazole-3-thione derivatives, confirmation of their individuality and structure, as well as the study of physical-chemical properties, for the further pharmacological screening. Materials and methods.2-((5-(hydroxy(phenyl)methyl)-4-R-4H-1,2,4-triazole-3-yl)thio)acetic acids were prepared by heating 5-(hydroxy(phenyl)methyl)-4-R-4H-1,2,4-triazol-3-thiones with chloroacetic acid. Subsequently, the synthesized thioacetic acids were subject for modification. Salts of 2-((5-(hydroxy(phenyl)methyl)-4-R-4H-1,2,4-triazole-3-yl)thio)acetic acids were obtained by reacting thioacetic acids with equivalents of sodium or potassium hydroxides.To obtain Iron (II), Copper (II) or Zinc (II) salts, half-molar amounts of the appropriate sulfates were added to the obtained solutions. Salts of 2-((5-(hydroxy(phenyl)methyl)-4-R-4H-1,2,4-triazole-3-yl)thio)acetic acids with organic bases were obtained by the reaction of acids with piperidine or morpholine in ethanol medium. Results.During the synthetic studies, 13 previously undescribed new compounds were obtained. The individuality of 2-((5-(hydroxy(phenyl)methyl)-4-R-4H-1,2,4-triazole-3-yl)thio)acetic acids and its salts after recrystallization was confirmed by thin layer chromatography. The structure of synthesized compounds was confirmed by the integrated use of elemental analysis and IR-spectrophotometry. Conclusions.The results of the work confirm the structure of the synthesized compounds, which shows the possibility of further biological investigation.Синтез і фізико-хімічні властивості 2-((5-(гідрокси(феніл)метил)-4-R-4H-1,2,4-тріазол-3-іл)тіо)ацетатних кислот та їхніх солейСьогодні в галузі фармації та медицини гостро стоїть питання про створення нових ліків вітчизняного виробництва, які замінили б дорогі закордонні аналоги. Тому актуальним є синтез нових вітчизняних біологічно-активних сполук. Відомо, що на основі 1,2,4-тріазолу останнім часом синтезовано велику кількість нових 3-тіо та 4-амінопохідних, серед них знайдені сполуки, що мають високі показники фармакологічної активності. Спираючись на досвід попередніх досліджень щодо створення нових оригінальних лікарських препаратів, постав...

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Section: Resultsmentioning

confidence: 82%

Section: Resultsmentioning

confidence: 99%

Section: Materials and Methods Of Researchmentioning

confidence: 99%

Section: Materials and Methods Of Researchmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis, physical and chemical properties of 2-((5-(hydroxy(phenyl)methyl)-4R-4H-1,2,4-triazole-3-yl)thio)acetic acids and its salts

Rud

Kaplaushenko

Yurchenko

2018

ZMJ

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Creation, Physical and Chemical Properties of Alkil-2-((5-Phenethyl-4-R-1,2,4- Triazole-3-Yl)thio)acet(propan,benz)imidates

Ігнатова¹,

Nagorna²,

Kaplaushenko³

et al. 2019

Asian J Pharm Clin Res

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Objective: The aim of this research was to synthesize and evaluate physical-chemical properties of 5-pheneyhyl-4-R-3-thio-1,2,4-triazole and to establish identity and structure of the synthesized compounds, namely alkil-2-((5-phenethyl-4-R-1,2,4-triazole-3-yl)thio)acet(propan,benz)imidates. Methods: As starting materials for synthesis of alkil-2-((5-phenethyl-4-R-1,2,4-triazole-3-yl)thio)acet(propan,benz)imidates, the corresponding 2-((5-phenethyl-4-R-1,2,4-triazole-3-yl)thio)aceto(propane,benzo)nitrile have been used. Synthesis has been set in the absolute alcohol medium (propanol or butanol alcohol) with chloroform, using the saturation with dry hydrogen chloride. Results: In this study, we have developed nine new compounds have been received as a result of synthetic transformations, the structure of synthesized compounds has been confirmed by modern complex of physical-chemical methods of analysis (1H NMR-spectroscopy, elemental analysis), and their individuality has been conducted on gas-liquid chromatograph Agilent 1260 Infinity HPLC equipped with a mass spectrometer Agilent 6120. Conclusion: As a result of the work, it was synthesized the new compounds of the series of alkil-2-((5-phenethyl-4-R-1,2,4-triazole-3-yl)thio) acet(propan,benz)imidates and was characterized by elemental analysis and proton nuclear magnetic resonance spectroscopic analysis.

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The synthesis of 4-amino-5-(quinolin-2-yl)-4H-1,2,4-triazole-3-thiol and its interaction with aldehydes

Zozulynets¹,

Kaplaushenko²,

Korzhova³

2021

J. org. pharm. chem.

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Aim. To synthesize 4-amino-5-(quinolin-2-yl)-4H-1,2,4-triazole-3-thiol and study its reactivity in the reactionwith aldehydes.Results and discussion. 4-Amino-5-(quinolin-2-yl)-4H-1,2,4-triazole-3-thiol was synthesized, and a number of 4-(ethyl, aryl)idenamino derivatives were obtained on its basis.Experimental part. Using a series of four successive reactions based on quinoline-2-carboxylic acid, 4-amino-5-(quinolin-2-yl)-4H-1,2,4-triazole-3-thiol was synthesized; its interaction with aldehydes allowed to obtain a number of 4-(ethyl, aryl)idenamino derivatives. The structure of all compounds synthesized was confrmed by IR and 1H NMR spectroscopy, as well as by elemental analysis, and their purity by thin layer chromatography.Conclusions. 4-Amino-5-(quinolin-2-yl)-4H-1,2,4-triazole-3-thiol has been synthesized. It has been found that its interaction with aldehydes leads to the formation of new 4-((ethyl, aryl)idenamino)-5-(quinolin-2-yl)-4H-1,2,4-triazole-3-thiols.Key words: 5-(quinolin-2-yl)-1,2,4-triazole-3-thiol; 4-arylidenamino derivatives; quinaldic acid; biologicalactivity

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Synthesis, physical-chemical properties and further transformation of 5-(quinoline-2-yl, 2-hydroxyquinoline-4-yl)-4-R-2,4-dyhydro-3Н-1,2,4-triazole-3-thiones

Cited by 3 publications

References 0 publications

Synthesis, physical and chemical properties of 2-((5-(hydroxy(phenyl)methyl)-4R-4H-1,2,4-triazole-3-yl)thio)acetic acids and its salts

Synthesis, physical and chemical properties of 2-((5-(hydroxy(phenyl)methyl)-4R-4H-1,2,4-triazole-3-yl)thio)acetic acids and its salts

Creation, Physical and Chemical Properties of Alkil-2-((5-Phenethyl-4-R-1,2,4- Triazole-3-Yl)thio)acet(propan,benz)imidates

The synthesis of 4-amino-5-(quinolin-2-yl)-4H-1,2,4-triazole-3-thiol and its interaction with aldehydes

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