Some novel Schiff bases of [1,2,4]triazole bearing haloarene moiety—synthesis and evaluation of antituberculosis properties and neutrophil function test

Castelino, Prakash Anil; Dasappa, Jagadeesh Prasad; Bhat, Kishore; Joshi, Sumith Ashok; Jalalpure, Sunil

doi:10.1007/s00044-015-1461-2

Cited by 17 publications

(10 citation statements)

References 24 publications

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“…have reported the design and synthesis of Schiff bases of 1,2,4-triazole-bearing haloarene moiety 173 ( Fig. 37 ) and screened for in vitro anti-TB properties using disc diffusion method (ZOI test) and microplate Alamar Blue assay (MABA) method (MIC test) towards Mtb H 37 Rv strain [ 155 ]. Compounds 173a and 173h having two fluorine atoms at positions 2 and 4 were found to exhibit the highest activity for antituberculosis screening as well as for neutrophil function test.…”

Section: Biological Activities Of 124-triazole Derivativesmentioning

confidence: 99%

An insight on medicinal attributes of 1,2,4-triazoles

Aggarwal

Sumran²

2020

European Journal of Medicinal Chemistry

214

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The present review aims to summarize the pharmacological profile of 1,2,4-triazole, one of the emerging privileged scaffold, as antifungal, antibacterial, anticancer, anticonvulsant, antituberculosis, antiviral, antiparasitic, analgesic and anti-inflammatory agents, etc. along with structure-activity relationship. The comprehensive compilation of work carried out in the last decade on 1,2,4-triazole nucleus will provide inevitable scope for researchers for the advancement of novel potential drug candidates having better efficacy and selectivity.

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Section: Biological Activities Of 124-triazole Derivativesmentioning

confidence: 99%

An insight on medicinal attributes of 1,2,4-triazoles

Aggarwal

Sumran²

2020

European Journal of Medicinal Chemistry

214

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“…Infectious diseases are one of the main causes of a large number of deaths [4,11,15]. It is common knowledge that more efficient antimicrobial compounds can be synthesized by combining two or more biologically active heterocyclic systems in a single molecular framework [1,3,8].…”

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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“…Bioactivity analysis indicated that the compounds have good inhibitory effects on the tested bacteria . Several studies have shown that triazole derivatives have biological activities such as anti‐inflammatory, antibacterial, antifungal, antiviral, anticancer, and antituberculosis . For example, Singh et al developed a series of substituted aryl azide compounds containing o ‐phenylenediamines, which exhibited antifungal activities .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antibacterial activity of chalcone derivatives containing thioether triazole

Chen

et al. 2020

Journal of Heterocyclic Chem

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The infection of Xanthomonas oryzae pv. Oryzae (Xoo), Ralstonia solanacearum (Rs), and Xanthomonas axonopodis pv. Citri (Xac) has become a major problem in agricultural production. In this study, a series of novel chalcone derivatives containing thioether triazoles were designed and synthesized. The structures of the novel compounds were systematically characterized via 1H‐NMR, 13C‐NMR, and HRMS. Moreover, the antibacterial activity results showed that E10, E11, E15, and E16 have adequate antibacterial activities against Xoo, Rs, and Xac. Among the different compounds, E15 exhibited remarkable inhibitory effect against Xac with an EC50 of 9.1 μg.mL‐1, which was better than that of commercial agent bismerthiazol (54.9 μg.mL‐1). In addition, the possible antibacterial mechanism of the target compound E15 against Xac was studied via scanning electron microscopy (SEM).

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Some novel Schiff bases of [1,2,4]triazole bearing haloarene moiety—synthesis and evaluation of antituberculosis properties and neutrophil function test

Cited by 17 publications

References 24 publications

An insight on medicinal attributes of 1,2,4-triazoles

An insight on medicinal attributes of 1,2,4-triazoles

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 antibacterial activity of chalcone derivatives containing thioether triazole

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