New 5-ylidene rhodanine derivatives based on the dispacamide A model

Guihéneuf, Solène; Paquin, Ludovic; Carreaux, François; Durieu, Emilie; Roisnel, Thierry; Meijer, Laurent; Bazureau, Jean Pierre

doi:10.1007/s11030-014-9509-7

Cited by 15 publications

(8 citation statements)

References 47 publications

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“…Moreover, performance of such condensation in aqueous solutions [48]; usage of atypical agents as well as ionic liquids [49]; the soluble polymer-supported synthesis [50] have also been investigated. Microwave assistant organic synthesis approach was also successfully employed [51,52].…”

Section: Modification Of the C5 Position Of The Thiazolidinone Corementioning

confidence: 99%

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

Kaminskyy

Kryshchyshyn

Lesyk

2017

European Journal of Medicinal Chemistry

151

133

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The presented review is an attempt to summarize a huge volume of data on 5-ene-4-thiazolidinones being a widely studied class of small molecules used in modern organic and medicinal chemistry. The manuscript covers approaches to the synthesis of 5-ene-4-thiazolidinone derivatives: modification of the C5 position of the basic core; synthesis of the target compounds in the one-pot or multistage reactions or transformation of other related heterocycles. The most prominent pharmacological profiles of 5-ene derivatives of different 4-thiazolidinone subtypes belonging to hit-, lead-compounds, drug-candidates and drugs as well as the most studied targets have been discussed. Currently target compounds (especially 5-en-rhodanines) are assigned as frequent hitters or pan-assay interference compounds (PAINS) within high-throughput screening campaigns. Nevertheless, the crucial impact of the presence/nature of C5 substituent (namely 5-ene) on the pharmacological effects of 5-ene-4-thiazolidinones was confirmed by the numerous listed findings from the original articles. The main directions for active 5-ene-4-thiazolidinones optimization have been shown: i) complication of the fragment in the C5 position; ii) introduction of the substituents in the N3 position (especially fragments with carboxylic group or its derivatives); iii) annealing in complex heterocyclic systems; iv) combination with other pharmacologically attractive fragments within hybrid pharmacophore approach. Moreover, the utilization of 5-ene-4-thiazolidinones in the synthesis of complex compounds with potent pharmacological application is described. The chemical transformations cover mainly the reactions which involve the exocyclic double bond in C5 position of the main core and correspond to the abovementioned direction of the 5-ene-4-thiazolidinone modification.

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Section: Modification Of the C5 Position Of The Thiazolidinone Corementioning

confidence: 99%

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

Kaminskyy

Kryshchyshyn

Lesyk

2017

European Journal of Medicinal Chemistry

151

133

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“…According to references [27][28][29][30][31], syntheses of these compounds result in (Z)-izomers. The same has recently been proved for 3-aminorhodanine derivatives [25]. Configuration on the exocyclic double-bond can be determined on the basis of NMR spectra where 1 H-NMR signals of the methine-group hydrogen for (Z)-isomers are more downfield compared to those expected for (E)-isomers.…”

Section: Resultsmentioning

confidence: 69%

“…Several modified methods [17][18][19][20][21][22][23][24][25][26] for the condensation of 3-aminorhodanine with aldehydes have been reported. They clearly show that in basic medium the components react to yield 3-amino-5-[(aryl)alkylidene]-2-thioxo-1,3-thiazolidin-4-ones 2.…”

Section: Introductionmentioning

confidence: 99%

(Z)-3-Amino-5-(pyridin-2-ylmethylidene)-2-thioxo-1,3-thiazolidin-4-one

Hirsova

Dolezel²,

Kučerová-Chlupáčová

et al. 2015

Molbank

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“…a Isolated yields which strongly indicates that the two 5-arylidene-4-oxo-2-thioxo-1,3-thiazolidine-1-yl moieties have both the Z-configuration (Guiheneuf et al, 2014). The unsymmetrical structure of 9a was also confirmed in the 13 C NMR spectrum because we observed two separated signals for the two methylene (CH=) carbons (d 133.1 and 133.4 ppm).…”

Section: Chemistrymentioning

confidence: 58%

Prospective study directed to the synthesis of unsymmetrical linked bis-5-arylidene rhodanine derivatives via “one-pot two steps” reactions under microwave irradiation with their antitumor activity

et al. 2014

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International audienceWe here report on the synthesis of new unsymmetrical linked bis-5-arylidene rhodanine derivatives with stereocontrolled Z-configuration. The 6 steps synthesis was achieved and the key steps are the construction of the two 5-arylidene rhodanine moieties using an “one-pot two-steps” method under microwave dielectric heating in a closed reactor. The intermediates 6, 7 and desired unsymmetrical compounds 9 have been also evaluated for their in vitro inhibition of cell proliferation (Huh7 D12, Caco2, MDA-MB 231, HCT116, and NCI-H727 tumoral cell lines). Two of all compounds have shown potent activity against Huh7 D12, Caco2, and MDA-MB 231

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New 5-ylidene rhodanine derivatives based on the dispacamide A model

Cited by 15 publications

References 47 publications

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

(Z)-3-Amino-5-(pyridin-2-ylmethylidene)-2-thioxo-1,3-thiazolidin-4-one

Prospective study directed to the synthesis of unsymmetrical linked bis-5-arylidene rhodanine derivatives via “one-pot two steps” reactions under microwave irradiation with their antitumor activity

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