Étude de dérivés 5-arylidène-2-thiohydantoïnes à potentialité immunomodulatrice et anticancéreuse

Chazeau, V; Cussac, M.; Boucherle, A

doi:10.1016/0223-5234(92)90140-v

Cited by 37 publications

(19 citation statements)

References 20 publications

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“…[14][15][16][17] Compounds containing the thiohydantoin structural motif have been identified to display a wide range of biological activities. For example, many of them exhibit anticonvulsant, 18 anti-epileptic, 19 antimicrobial, 20 antiviral, 21 antineoplastic, 22 hypolipidemic, 23 antithrombotic, 24 and potential antitumor activities, 25,26 etc. Several derivatives are employed either as established drugs in clinical practice 2 or as fungicides and herbicides in agriculture.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and cytotoxicity of palladium(II) complex of 3-[(2-hydroxy-benzylidene)-amino]-2-thioxo-imidazolidin-4-one

Šmit

Pavlovic

Radosavljevic-Mihailovic³

et al. 2013

JSCS

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The polydentate ligand, 3-[(2-hydroxy-benzylidene)-amino]-2-thioxo-imidazolidin-4-one, was synthesized by intermolecular cyclocondensation reaction of 2-hydroxybenzaldehyde thiosemicarbazone and ethylchloroacetate. Novel palladium(II) complex was obtained by nucleophilic substitution of both DMSO ligands from cis-[Pd(DMSO)2Cl2] with iminic nitrogen and thiolactamic sulfur from ligand. The structure of compounds was characterized on the basis of their spectral data. The cytotoxic activity of the ligand and palladium(II) complex was studied on tumor cell lines: human colon carcinoma HCT-116 and SW-480 cells using MTT viability test. The results show that investigated palladium(II) complex has significantly greater cytotoxic effect compared to ligand. [Projekat Ministarstva nauke Republike SRbije, br. 172011 and III41010

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Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and cytotoxicity of palladium(II) complex of 3-[(2-hydroxy-benzylidene)-amino]-2-thioxo-imidazolidin-4-one

Šmit

Pavlovic

Radosavljevic-Mihailovic³

et al. 2013

JSCS

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“…These compounds are also obtained in aldolic and related condensations with acetone 394 or its oxime 395 ; aromatic 396,397 and heteroaromatic methylketones 398,399 ; cyclic alkylketones 400 ; acetates 401 ; propionates 402 ; acetoacetates 403 ; cyanoacetates 404 ; nitroalkanes 405 ; benzodiazepinones 406 ; imidazolinones 407 ; indoles 408 ; 2-methylquinolines 409 ; pyrazinones 410 ; thiazolidinediones [411][412][413][414][415] and xanthinones 416 In the reaction of isatins with some cyclic ketones, such as 4-hydroxy-2H-benzopyran-2-one 417 , the initial dioxindole formed reacts with a second equivalent of the ketone yielding a 3,3-disubstituted oxindole.…”

Section: Scheme 96mentioning

confidence: 99%

The chemistry of isatins: a review from 1975 to 1999

Silva¹,

Garden²,

Pinto³

2001

J. Braz. Chem. Soc.

860

447

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Isatinas (1H-indol-2,3-diona) são compostos de grande versatilidade sintética, podendo ser utilizados na obtenção de diversos sistemas heterociclos, como derivados indólicos e quinolínicos, o que as tornam importantes matérias-primas na síntese de fármacos. Isatinas também têm sido detectadas em tecidos de mamíferos, o que tem despertado o interesse em seu estudo como moduladores em diversos processos bioquímicos. Os avanços na aplicação de isatinas em síntese orgânica, bem como na compreensão de seus efeitos biológicos e farmacológicos nos últimos vinte e cinco anos encontram-se relatados nesta revisão e seus respectivos materiais suplementares.Isatins (1H-indole-2,3-dione) are synthetically versatile substrates, where they can be used for the synthesis of a large variety of heterocyclic compounds, such as indoles and quinolines, and as raw material for drug synthesis. Isatins have also been found in mammalian tissue and their function as a modulator of biochemical processes has been the subject of several discussions. The advances in the use of isatins for organic synthesis during the last twenty-five years, as well as a survey of its biological and pharmacological properties are reported in this review and in the accompanying supplementary information.

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“…Thus, hydantoin ( 6 ) derivatives are represented by approved drugs (Phenytoin, Fosphenytoin), pesticides (Imiprothrin, Iprodione), or inhibitors of matrix metalloproteinases (MMPs). 18 Thiohydantoin ( 7 ) derivatives have been identified as antimicrobials 19 and antitumor 20 agents with topoisomerase I inhibitory activities. 21 Rhodanine ( 8 ) derivatives are well known beta-lactamase inhibitors.…”

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confidence: 99%

Isatin derivatives with activity against apoptosis-resistant cancer cells

Evdokimov

Magedov

McBrayer

et al. 2016

Bioorganic & Medicinal Chemistry Letters

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In a search of small molecules active against apoptosis-resistant cancer cells, a series of isatin-based heterocyclic compounds were synthesized and found to inhibit proliferation of cancer cell lines resistant to apoptosis. The synthesis of these compounds involved a condensation of commercially available, active methylene heterocycles with isatin proceeding in moderate to excellent yields. The heterocyclic scaffolds prepared in the current investigation appear to be a useful starting point for the development of agents to fight cancers with apoptosis resistance, and thus, associated with dismal prognoses.

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Étude de dérivés 5-arylidène-2-thiohydantoïnes à potentialité immunomodulatrice et anticancéreuse

Cited by 37 publications

References 20 publications

Synthesis, characterization and cytotoxicity of palladium(II) complex of 3-[(2-hydroxy-benzylidene)-amino]-2-thioxo-imidazolidin-4-one

Synthesis, characterization and cytotoxicity of palladium(II) complex of 3-[(2-hydroxy-benzylidene)-amino]-2-thioxo-imidazolidin-4-one

The chemistry of isatins: a review from 1975 to 1999

Isatin derivatives with activity against apoptosis-resistant cancer cells

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