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

Jacobine, Alexander M.; Posner, Gary H.

doi:10.1021/jo201561t

Cited by 41 publications

(14 citation statements)

References 37 publications

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“…The exploration of a-chloro-b,g-alkenoate esters in such type of multicomponent reactions led to the formation of 5-(Z)-alkylidene-2-thioxo-1,3-thiazolidin-4-ones (36) which are uncommon compounds [115].…”

Section: Simultaneous Formation Of Heterocycle and C5 Exocyclic Doublmentioning

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: Simultaneous Formation Of Heterocycle and C5 Exocyclic Doublmentioning

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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“…These new multicomponent reactions were done in a green method in which the yields of biologically interesting structure are typically 90 %. 5-( Z)-Alkylidene-2-thioxo-1,3-thiazolidin-4-ones 39 (rhodanine derivatives) were prepared by the reaction of in situ generated dithiocarbamates [41] with racemic α-chloro-β,γ-alkenoate esters 36 (Scheme 9.19). ILs have attracted extensive research interest in recent years as environmentally benign solvents of their favorable properties.…”

Section: Green Synthesis Of Rhodanines and Tzdsmentioning

confidence: 99%

Synthesis and Synthetic Applications of Biologically Interesting Rhodanine and Rhodanine-Based Scaffolds

Rostamnia

Doustkhah

2014

Green Chemistry: Synthesis of Bioactive Heterocycles

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Rhodanine and thiazolidinone (TZD) heterocycles are attractive targets in organic and medicinal chemistry owing to their potency in a wide spectrum of biological activities and can also serve as synthetic intermediates for many kinds of pharmaceuticals or drug precursors. Consequently, looking for efficient and concise green methods for the synthesis of these types of compounds is a major challenge in chemistry. As a result, many green methods have been used to synthesize structurally complex and diverse rhodanine and TZDs in recent years. The purpose of this chapter is to discuss the recent green synthesis of the rhodanine and TZD heterocyclic scaffolds including aqueous medium synthesis, ionic liquid, microwave, ultrasonic irradiation, solvent-free methods, solid catalysts, such as mesoporous, magnetic nanoparticles, etc.

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“…Multicomponent processes are undoubtedly one of the most efficient approaches to forming several important motifs in modern organic synthesis and pharmaceutical synthesis [24][25][26]. For example, rhodanines have been successfully synthesized through multicomponent processes [27][28][29][30][31][32][33]. However, almost all known methods involving multicomponent reactions cannot achieve the synthesis of 5-unsubstituted rhodanines.…”

Section: Introductionmentioning

confidence: 99%