Synthesis of Novel Highly Functionalized 4-Thiazolidinone Derivatives from 4-Phenyl-3-thiosemicarbazones

Benmohammed, Abdelmadjid; Khoumeri, Omar; Djafri, Ayada; Terme, Thierry; Vanelle, Patrice

doi:10.3390/molecules19033068

Cited by 32 publications

(22 citation statements)

References 24 publications

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“…Receptor 1 was synthesized by reacting anthracene‐1,8‐dicarbaldehyde and N ‐phenylhydrazinecarbothioamide in ethanol using acetic acid as a catalyst in 64% yield. Receptor 1 was characterized by high‐resolution mass spectrometry, 1 H NMR and 13 C NMR.…”

Section: Resultsmentioning

confidence: 99%

A Hydrogen Pyrophosphate Selective Anion Receptor Based on Thiosemicarbazone

Pandian¹,

Srinivasadesikan

Lin

et al. 2017

Bulletin Korean Chem Soc

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A novel rigid anion receptor 1 containing thiosemicarbazone groups were synthesized. Receptor 1 displayed competitive turn‐off fluorescence and colorimetric response for hydrogen pyrophosphate. This recognition process was confirmed by UV–vis, fluorescence titrations. A detailed analysis of the TD‐density functional theory calculations was consistent with the observed colorimetric experiments. These experiments revealed that the colorimetric and fluorescent response is triggered by thiourea/ HP2O73− hydrogen bonding.

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Section: Resultsmentioning

confidence: 99%

A Hydrogen Pyrophosphate Selective Anion Receptor Based on Thiosemicarbazone

Pandian¹,

Srinivasadesikan

Lin

et al. 2017

Bulletin Korean Chem Soc

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“…Therefore, there is continuous need for the search and development of more effective and reliable anticonvulsant drugs. As the literature survey reveals that indoline‐2,3‐dione (isatin) derivatives have exhibited potent CNS depressant and anticonvulsant activities in many research papers as well as the Schiff base with 4‐thiazolidinone derivatives possess remarkable anticonvulsant activity and in continuation of our earlier efforts for search of novel anticonvulsant agents. In the present work our objective was to develop novel hybrid heterocyclic molecule having indoline‐2,3‐dione moiety coupled with thiazolidinone nucleus having appropriate pharmacophors with the hope to get novel compounds with significant and potential anticonvulsant activity and minimal toxic side effects.…”

Section: Introductionmentioning

confidence: 95%

Synthesis, Biological Activity, and Docking Study of Novel Isatin Coupled Thiazolidin‐4‐one Derivatives as Anticonvulsants

Nikalje

Ansari

Bari

et al. 2015

Archiv der Pharmazie

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A series of 2-(substituted-phenyl)-3-(2-oxoindolin-3-ylidene)amino)-thiazolidin-4-one derivatives were designed and synthesized under microwave irradiation, using an eco-friendly, efficient, microwave-assisted synthetic protocol that involves cyclocondensation of 3-substituted benzylidine-hydrazono-indolin-2-one 3a-j with thioglycolic acid in dimethyl formamide (DMF) as solvent and anhydrous zinc chloride as a catalyst, keeping in view the structural requirement of the pharmacophore. The intermediate compounds 3a-j were obtained by condensation of the hydrazone of indoline-2,3-dione with aromatic aldehydes. The synthesized derivatives were evaluated for CNS depressant activity and anticonvulsant activity in mice using the maximal electroshock seizure (MES) and subcutaneous pentylenetetrazole (sc-PTZ) induced seizure tests. All the derivatives showed good CNS depressant activity and showed protection in the MES test, indicative of their ability to inhibit the seizure spread. A histopathological study was performed to evaluate liver toxicity caused by the synthesized compounds. The compounds were nontoxic. A computational study was performed, in which log P values were calculated experimentally. Virtual screening was performed by molecular docking of the designed compounds into the ATP binding sites of the NMDA and AMPA receptors, to predict if these compounds have analogous binding modes.

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“…[17] Also, it has been reported with thioureas and dialkyl acetylenedicarboxylates in EtOH/rt, [18a] with diethyl-but-2-ynedioate and dimethyl but-2-ynedioate in DMF/rt, [18b] To the best of our knowledge only one report is available for the synthesis of proposed pharmacological active 4-thiazolidinone acetates. For example, imino-1,3-thiazolidin-4-one have been synthesized with thiosemicarbazones and Dimethylacetylenedicarboxylate in AcOH/EtOH as well as with 2-bromoacetate in methanol/reflux/1 h, AcONa/EtOH/reflux/1-3 h. [20] The literature method revealed that the 4-thiazolidinone acetate derivatives were prepared by acid and base catalysed reaction of thiosemicarbazones and diethylacetylenedicarboxylate at 85°C. The authors were isolated the final product in two steps.…”

Section: Introductionmentioning

confidence: 99%

Highly Efficient, Combinatorial and Catalyst‐Free Approach for the Synthesis of 2‐Benzylidenehydrazono‐3‐phenyl‐4‐thiazolidinone‐5‐acetates in Ethanol

Jangale

Dalal

2019

ChemistrySelect

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We have designed a sustainable, catalyst‐free, combinatorial protocol for the synthesis of highly functionalized thiazolidinone acetate derivatives via multicomponent reaction of aromatic aldehydes, N‐phenylhydrazinecarbothioamide and dimethoxyacetylenedicarboxylate in the ethanol. A consecutive one pot two step environmentally benign procedure has been developed for the synthesis of 2‐Benzylidenehydrazono‐3‐Phenyl‐4‐Thiazolidinone‐5‐Acetate derivatives by adopting regioselective thermal annulation with the operational simplicity with isolation of pure products without using chromatographic purification.

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Synthesis of Novel Highly Functionalized 4-Thiazolidinone Derivatives from 4-Phenyl-3-thiosemicarbazones

Abstract: Abstract:We present herein the synthesis in good yields of two series of highly functionalized thiazolidinone derivatives from the reactions of various 4-phenyl-3-thio-semicarbazones with ethyl 2-bromoacetate and diethyl acetylenedicarboxylate, respectively.

Cited by 32 publications

References 24 publications

A Hydrogen Pyrophosphate Selective Anion Receptor Based on Thiosemicarbazone

A Hydrogen Pyrophosphate Selective Anion Receptor Based on Thiosemicarbazone

Synthesis, Biological Activity, and Docking Study of Novel Isatin Coupled Thiazolidin‐4‐one Derivatives as Anticonvulsants

Highly Efficient, Combinatorial and Catalyst‐Free Approach for the Synthesis of 2‐Benzylidenehydrazono‐3‐phenyl‐4‐thiazolidinone‐5‐acetates in Ethanol

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