A new approach for the synthesis of bioactive heteroaryl thiazolidine-2,4-diones

Ibrahim, Magdy A.; Abdel-Hamed, Mohamed Abdel-Megid; El-Gohary, Naser

doi:10.1590/s0103-50532011000600019

Cited by 43 publications

(17 citation statements)

References 22 publications

(29 reference statements)

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“…Though, presented protocols for 235e237 [75,483] are not persuasive, taking into consideration the transformation (instability) of 4-thiazolidinone core in the basic medium (see below) [1,2,6].…”

Section: Hydrolytic Cleavagementioning

confidence: 99%

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

Kaminskyy

Kryshchyshyn

Lesyk

2017

European Journal of Medicinal Chemistry

139

129

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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: Hydrolytic Cleavagementioning

confidence: 99%

“…5-Ene-4-thiazolidinones are often the intermediates in the above mentioned tandem reactions involving the hetero-Dielse-Alder reaction [67,69,483,484,490] (Scheme 118).…”

Section: Hetero-diels-alder Reaction and Related Processesmentioning

confidence: 99%

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

Kaminskyy

Kryshchyshyn

Lesyk

2017

European Journal of Medicinal Chemistry

139

129

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“…Magdy allowed to obtain the corresponding pyrazole-thiazolidinones 3.9 [94]. Using hydrazine hydrate the structure of final compounds depended on the reaction medium.…”

Section: The Main Approaches To the Synthesis Of 4-thiazolidinones Wimentioning

confidence: 99%

Synthetic approaches, structure activity relationship and biological applications for pharmacologically attractive pyrazole/pyrazoline–thiazolidine-based hybrids

Havrylyuk

Roman

Lesyk

2016

European Journal of Medicinal Chemistry

129

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The features of the chemistry of 4-thiazolidinone and pyrazole/pyrazolines as pharmacologically attractive scaffolds were described in a number of reviews in which the main approaches to the synthesis of mentioned heterocycles and their biological activity were analyzed. However, the pyrazole/pyrazoline-thiazolidine-based hybrids as biologically active compounds is poorly discussed in the context of pharmacophore hybrid approach. Therefore, the purpose of this review is to summarize the data about the synthesis and modification of heterocyclic systems with thiazolidine and pyrazoline or pyrazole fragments in molecules as promising objects of modern bioorganic and medicinal chemistry. The description of biological activity was focused on SAR analysis and mechanistic insights of mentioned hybrids.

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“…Chromonyl-2,4-thiazolidinediones 118 were prepared by the Knoevenagel condensation of 2,4-TZDs (2,4-thiazolidine diones) 117 with 3-formylchromones 1a,b,n in glacial acetic acid containing freshly fused sodium acetate (Scheme 57) [84][85][86].…”

Section: Scheme 56mentioning

confidence: 99%