Synthesis of fused heterocyclic compounds on the basis of 2-thioxo-1,3-thiazolidin-4-ones

Yarovenko, V. N.; Nikitina, A. S.; Заварзин, И. В.; Krayushkin, M. M.; Kovalenko, L. V.

doi:10.1134/s1070428007090175

Cited by 8 publications

(3 citation statements)

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“…Similar 2-hydroxybenzylidene rhodanine derivatives reacted with malononitrile to give fused chromeno[4 0 ,3 0 :4,5]pyrano[2,3-d] thiazol-6-ones 242. Due to instability of rhodanines in basic medium at high temperatures the yields of the cyclocondensation products are low [458] (Scheme 117).…”

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

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: 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

151

133

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“…The literature 12 shows that the reaction between α, β -unsaturated ketones and a difunctional nucleophile such as phenylhydrazine could cyclize to produce pyrazoline. Unfortunately, the results obtained confirmed that pyrazoline derivatives 3a-3f were not detected (Scheme 2).…”

Section: Synthesis Of 3-methylrhodanine Derivativesmentioning

confidence: 99%

Synthesis and in vitro α-glucosidase inhibitory activity of some of the derivatives of 3-methylrhodanine

2022

Sci. Tech. Dev. J.

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In the further research and synthesis of highly bioactive 3-methylrhodanine derivatives, the preparation of benzylidene rhodanines followed by bicyclization to form pyrazole compounds has been undertaken. Using a convenient and simple method, twelve compounds have been synthesized including six benzylidene rhodanine derivatives ranging from a good to excellent yield, with four phenylhydrazone and two pyrazole derivatives at a low yield. The structures of all synthesized compounds were elucidated by spectral methods of analysis. Among them, six heterocyclic compounds, namely 4-( 2-phenylhydrazono)-5-benzylidene-3-methylthiazolidine-2-thione (3'a-3'd), 3-(4-nitrophenyl)-2-phenyl-2,6-dihydro-5H-pyrazolo[3,4-d]thiazole-5-thione (3''e), and 3-(4cyanophenyl)-2-phenyl-2,6-dihydro-5H-pyrazolo[3,4-d]thiazole-5-thione (3''f) were synthesized for the first time. The synthesized compounds were evaluated in vitro against α-glucosidase and exhibited promising antidiabetic activity with IC 50 values ranging from 11.3 to 21.9 µM.

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“…10 5-(o-Hydroxybenzylidene)-4-thiazolidinones are readily available reagents for the synthesis of compounds with bulky C-5 fragments and new heterocycles (e.g., isothiocumarins, (thio)pyrano[2,3-d]thiazoles). 2,18 For the synthesis of simple 5-(2-hydroxybenzylidene)-4-aminothiazol-2(5H)-ones the known Knoevenagel condensation was used.…”

Section: Letter Syn Lettmentioning

confidence: 99%