Electrochemical synthesis of 1,2,4-triazol-3-thione derivatives: Anodic oxidation of N-thioamidohydrazones

Chmekh, Rania; Tapsoba, Issa; Medini, Hayet; Maisonhaute, Emmanuel; Benkhoud, Mohamed Lamine; Boujlel, Khaled

doi:10.1016/j.jelechem.2006.09.014

Cited by 8 publications

(4 citation statements)

References 13 publications

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“…The use of CD complexes with pharmaceutically active compounds is attractive for the preparation of electrochemical sensors especially in pharmaceutical and biomedical analysis. It has been shown that cyclodextrin represents a nonelectroactive host while pharmaceutical compounds are an electroactive guests [24][25][26][27].…”

Section: Resultsmentioning

confidence: 99%

Electrochemical determination of sertraline in pharmaceutical formulation and serum using a gold electrode in a pH 8.4 bicarbonate solution

et al. 2021

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The electrochemical characterization of sertraline at gold electrode was examined by cyclic voltammetry measurements (CV) in pH 8.4 bicarbonate buffer. Then Au electrode was evaluated for the quantitative determination of sertraline using square wave voltammetry (SWV). To enhance the sensitivity during the drug determination, (2-hydroxypropyl)-β-cyclodextrin (HPβCD) and β-cyclodextrin (βCD) inclusion complexes were employed. Using the proposed SWV technique, the anodic current peak was linear within a concentration range of 0.1-0.5 µM with a limit of detection (LOD) of 2.0 × 10 -8 M and a limit of quantification (LOQ) of 6.7 × 10 -8 M. In the case of inclusion complex of the sertraline with HPβCD, a good linearity range of 0.1-0.9 µM was obtained with a LOD of 2.6 × 10 -8 M and a LOQ of 8.8 × 10 -8 M. The gold electrode revealed the same linearity range for inclusion complex of the sertraline with βCD with a LOD and a LOQ being 2.6 × 10 -8 and 8.6 × 10 -8 M, respectively. Comparing the regression equations, it can be concluded that the sensitivity in the presence of inclusion complex can be up to 5 times higher. The applicability of the developed method was confirmed by the analysis of this drug in pharmaceutical formulation and in human serum spiked with sertraline standard. The comparison to HPLC method was successfully performed.

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Section: Resultsmentioning

confidence: 99%

Electrochemical determination of sertraline in pharmaceutical formulation and serum using a gold electrode in a pH 8.4 bicarbonate solution

et al. 2021

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“…5, one can observes that in the presence of various concentration of 2,6-lutidine as a base, the oxidation peak of the substrate 1a shift toward cathodic potential and the current increase. This behavior highlights the formation of anionic species by deprotonation which are easily oxidable than the starting substrate [6]. When no other base is added in the medium, the starting substrate acts as a base to deprotonate the cation radical.…”

Section: Heterogeneous Oxidation Of N-thioamidoimidatesmentioning

confidence: 96%

“…Recent works investigated in our team show the possibility to access to bicyclic or small heterocyclic derivatives by means of electrochemistry [4][5][6]. We previously demonstrated that the cathodic reduction of amines derivatives leads to heterocyclic products like oxazolo [5,4-d]oxazoles after transfer of one electron per molecule [7].…”

Section: Introductionmentioning

confidence: 97%

Mechanistic investigation of N-thioamidoimidates: Oxidation by heterogeneous and homogeneous electron transfers

Haouas

Tapsoba

Boujlel

2007

Electrochimica Acta

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“…The resulting oil was washed twice with 5 mL of petroleum ether and allowed to stay at room temperature for 3-4 days to crystallize giving the amidines 2. The solid was purified by recrystallization in absolute ethanol (27)(28)(29)(30). …”

Section: Synthesis Of N-thioamido Imidatesmentioning

confidence: 99%

Reactivity of N-thioamido amidines with halogenated alkyl derivatives: synthesis of 4,5-disubstituted 2-alkylaminothiazoles

Khilifi

Raouafi

Tapsoba

et al. 2008

Journal of Sulfur Chemistry

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2-Bromoacetate ethyl ester 4, 2-chloroacetonitrile 5, 2-bromo-1-(4-nitrophenyl)ethanone 6, and 2-chloroacetone 7 react with N -thioamido amidines 3 to yield the corresponding 4,5-disubstituted 2-alkylamino thiazoles 8, 9, 10, and 11 after the release of an amine molecule. The reaction of the amidines 3 with benzyl bromide 12, 4-chlorobutyronitrile 13, 3-bromopropionate ethyl ester 14, 3-chloropropionate ethyl ester 15, and 4-nitrobenzyl chloride 16 does not lead to the cyclic derivatives but gives opened-ring intermediates 17, 18, 19, 20, and 21. The cyclization mechanism is discussed on the basis of the study of the opened-ring intermediates which have been isolated in some cases and the AM1 and PM3 semi-empirical energetic calculations.

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Electrochemical synthesis of 1,2,4-triazol-3-thione derivatives: Anodic oxidation of N-thioamidohydrazones

Cited by 8 publications

References 13 publications

Electrochemical determination of sertraline in pharmaceutical formulation and serum using a gold electrode in a pH 8.4 bicarbonate solution

Electrochemical determination of sertraline in pharmaceutical formulation and serum using a gold electrode in a pH 8.4 bicarbonate solution

Mechanistic investigation of N-thioamidoimidates: Oxidation by heterogeneous and homogeneous electron transfers

Reactivity of N-thioamido amidines with halogenated alkyl derivatives: synthesis of 4,5-disubstituted 2-alkylaminothiazoles

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