A practical access to novel 2-amino-5-arylidene-1,3-thiazol-4(5H)-ones via sulfur/nitrogen displacement under solvent-free microwave irradiation

Bourahla, Khadidja; Derdour, Aïcha; Rahmouni, Mustapha; Carreaux, François; Bazureau, Jean Pierre

doi:10.1016/j.tetlet.2007.06.078

Cited by 43 publications

(19 citation statements)

References 32 publications

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“…Based on the Knoevenagel condensation the efficient method for 5ethoxy-4-thiazolidinones synthesis (5) using triethylorthoformate was described [32,62e66], the latter (5) can be easily converted Knoevenagel condensation often may be a stage in the tandem and/or domino reactions whilst the corresponding 5-ene-thiazolidinones appear as intermediates in the synthesis of fused thiazolidinone-based heterocycles (see bellow) [67e69] or simple molecules of other thiazolidinone subtypes. For example, an efficient approach to the 5-ene-2-amino-4-thiazolidinones obtaining via sulfur/nitrogen displacement [70] was the base for the development of multicomponent reactions involving Knoevenagel condensation [71]. The one-pot reaction of isatin derivatives, rhodanine and secondary amines (magnesium oxide nanoparticles used as heterogeneous catalyst, water medium, r.t.) is an efficient green approach to the preparation of novel isatin-thiazolidinone based conjugates (7) [72] (Scheme 4).…”

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

145

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

145

133

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“…To generate compounds with general structure B, several procedures have been reported; [22][23][24][25] we adapted a recently published synthetic strategy that describes a one-pot, multicomponent, microwave-assisted reaction that allows the desired final compounds to be obtained directly (Scheme 2). [22] The methodology involves 5-aryl-2-furaldehyde 4 (synthesized as reported above), rhodanine, and several secondary or primary amines (11 a-d) that catalyze a Knoevenagel condensation between the aldehyde and rhodanine, and then act as nucleophiles in the displacement of the thiocarbonyl sulfur.…”

Section: Chemistrymentioning

confidence: 99%

“…In fact, the experimental J values of these derivatives are in agreement with those previously reported for analogous 4-thiazolidinones. [22][23][24][25][27][28][29][30] Biological activity and docking studies…”

Section: Chemistrymentioning

confidence: 99%

A Versatile and Practical Synthesis toward the Development of Novel HIV‐1 Integrase Inhibitors

et al. 2011

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As a continuation of our previous work, which resulted in the identification of a new hit compound as an HIV-1 integrase inhibitor, three novel series of salicylic acid derivatives were synthesized using three versatile and practical synthetic strategies and were assayed for their capacity to inhibit the catalytic activity of HIV-1 integrase. Biological evaluations revealed that some of the synthesized compounds possess good inhibitory potency in enzymatic assays and are able to inhibit viral replication in MT-4 cells at low micromolar concentrations. Finally, docking studies were conducted to analyze the binding mode of the synthesized compounds within the DNA binding site of integrase in order to refine their structure-activity relationships.

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“…Rhodanines (2-thioxo-1,3-thiazolidin-4-ones) are 5-membered ring sulfur/nitrogen heterocycles some of which have antimalarial, antibacterial, antifungal, antiviral, antitumor, anti-inflammatory or herbicidal activities. 6 5- Arylidene rhodanines are common, 7–14 whereas 5- alkylidene rhodanines are rare. 15–17 In one direct comparison, 5- alkylidene rhodanine A was more potent as a class C β-lactamase inhibitor than the corresponding vinylogous 5- arylidene rhodanine B (Figure 1).…”

mentioning

confidence: 99%

Three-Component, One-Flask Synthesis of Rhodanines (Thiazolidinones)

Jacobine

Posner

2011

J. Org. Chem.

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5-(Z)-Alkylidene-2-thioxo-1,3-thiazolidin-4-ones (rhodanine derivatives) were prepared by reaction of in situ-generated dithiocarbamates with recently reported racemic α-chloro-β,γ-alkenoate esters. This multicomponent sequential transformation performed in one reaction flask represents a general route to this medicinally valuable class of sulfur/nitrogen heterocycles. Using this convergent procedure, we prepared an analog of the drug epalrestat, an aldose reductase inhibitory rhodanine.

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A practical access to novel 2-amino-5-arylidene-1,3-thiazol-4(5H)-ones via sulfur/nitrogen displacement under solvent-free microwave irradiation

Cited by 43 publications

References 32 publications

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

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

A Versatile and Practical Synthesis toward the Development of Novel HIV‐1 Integrase Inhibitors

Three-Component, One-Flask Synthesis of Rhodanines (Thiazolidinones)

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