Anticancer properties of 4-thiazolidinone derivatives depend on peroxisome proliferator-activated receptor gamma (PPARγ)

Szychowski, Konrad A.; Leja, Marcin L.; Kaminskyy, Danylo; Kryshchyshyn, Anna; Binduga, Urszula E.; Pinyazhko, O. R.; Lesyk, Roman; Tobiasz, Jakub; Gmiński, Jan

doi:10.1016/j.ejmech.2017.09.071

Cited by 44 publications

(48 citation statements)

References 33 publications

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“…In 1 H NMR, chemical shift at 3.90 ppm (because of S─CH 2 ─ protons) as singlet further indicated the formation of (4). Finally, 4thiazolidonone derivatives (5)(6)(7)(8)(9)(10)(11)(12)(13)(14) showed alkenic (C═C) bond stretching frequency in the region of 1550-1600 cm À1 while alkenic (H─C═C) proton appeared as singlet between 7.6 and 8.3 ppm that confirmed the formation of compounds. Additionally, formation of compounds (5)(6)(7)(8)(9)(10)(11)(12)(13)(14) was confirmed by 13 C NMR because of the presence of the characteristic carbonyl (─C═O) peak in the range of 164-168 ppm.…”

Section: Resultsmentioning

confidence: 86%

“…Present study was undertaken to synthesize the analogues of 4-thiazolidinone derivatives. Target compounds (5)(6)(7)(8)(9)(10)(11)(12)(13)(14) were obtained in a three step reaction procedure (Scheme 1). First step involves the synthesis of 1-(2-chlorobenzyl)-3-phenylthiourea (3) by the reaction of 2-chlorobenzylamine (1) and phenyl isothiocyanate (2) in toluene at room temperature.…”

Section: Resultsmentioning

confidence: 99%

“…In the second step, anhydrous sodium acetate assisted cyclization of (3) in absolute ethanol and chloroacetic acid yielded 3-(2chlorobenzyl)-2-(phenylimino)-1,3-thiazolidin-4-one (4). The lead compounds (5)(6)(7)(8)(9)(10)(11)(12)(13)(14) were obtained in the third step by Knoevenagel condensation of 3-(2-chlorobenzyl)-2-(phenylimino)-1,3-thiazolidin-4-one (4) with different aromatic aldehydes in absolute ethanol. All compounds (5)(6)(7)(8)(9)(10)(11)(12)(13)(14) were characterized by FTIR, 1 H NMR, 13 C NMR, and mass spectral studies.…”

Section: Resultsmentioning

confidence: 99%

“…Enantiomers are present in the crystal packing. They are generated by rotation around C(6)-C (7) and N(2)-C (14) Table 1 Binding energy of molecular docking of compounds (5)(6)(7)(8)(9)(10)(11)(12)(13)(14) with protein CAIX (PDBID = 3IAI) and residues of protein involved in binding.…”

Section: Computational Studiesmentioning

confidence: 99%

“…In the view of versatile biological importance of 4thiazolidinone derivatives and to evaluate their anticancer effect, we report the synthesis, characterization, molecular docking, and anticancer evaluation of 4-thiazolidinone analogues (5)(6)(7)(8)(9)(10)(11)(12)(13)(14). The results of the findings are discussed herein.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Characterization, Molecular Docking, and Anticancer Evaluation of 4‐Thiazolidinone Analogues

Mushtaque¹,

Avecilla

Hafeez

et al. 2019

Journal of Heterocyclic Chem

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Scaffolds containing one or more heteroatoms are ubiquitous in nature and are responsible for almost every biological processes in flora and fauna. The fact that heterocyclic cores have high propensity for biological targets, several nitrogen, oxygen, and sulfur‐containing heterocyclic compounds have been reported in the last few decades. One such intriguing class is 4‐thiazolidinone that exhibit diverse range of pharmacological activities. In the present study, we report synthesis, characterization, molecular docking, and anticancer evaluation of 10 new 4‐thiazolidinone analogues (5–14). One of the compounds (11) was structurally characterized using single crystal X structure. Anticancer evaluation against hepatocellular carcinoma cell line (HepG2) revealed that compound (7) was the most potent (IC50 = 75 μM) while other showed moderate to low activity (85–530 μM). To underpin the druggability and possible modes of action, drug‐likeness was determined and docking studies were carried out against β‐carbonic anhydrase receptor (PDB ID: 3IA). Attempts have also been made to establish a structure–activity relationship of the reported compounds.

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Section: Resultsmentioning

confidence: 86%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Computational Studiesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Synthesis, Characterization, Molecular Docking, and Anticancer Evaluation of 4‐Thiazolidinone Analogues

Mushtaque¹,

Avecilla

Hafeez

et al. 2019

Journal of Heterocyclic Chem

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Design, synthesis, and molecular docking studies of thiazolidinediones as PPAR‐γ agonists and thymidylate synthase inhibitors

Nazreen

2021

Archiv der Pharmazie

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New thiazolidine‐2,4‐dione hybrids were designed and synthesized as potential peroxisome proliferator‐activated receptor (PPAR)‐γ agonists and thymidylate synthase inhibitors. All the synthesized compounds follow Lipinski's and Veber's rules and possess the desired pharmacokinetics properties. The PPAR‐γ transactivation results displayed that compounds 12 (78.9%) and 11 (73.4%) were the most active compounds and they increased PPAR‐γ gene expression by 2.2‐ and 2.4‐fold, respectively. Compounds 12, 11, and 8 showed promising cytotoxicity, with IC50 values ranging from 1.4 to 4.5 μM against MCF‐7 cells and from 1.8 to 8.4 μM against HCT‐116 cells. Compounds 11 and 12 also inhibited thymidylate synthase with IC50 values of 5.1 and 3.2 μM, respectively, confirming their mode of action as thymidylate synthase inhibitors. Finally, molecular docking studies supported the in vitro biological activity results.

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One‐pot multicomponent designing of novel 2‐imino‐4‐arylidene‐1,3‐thiazolidin‐4‐one

Amer

Abdelhamid

Elnakeeb

et al. 2022

Journal of Heterocyclic Chem

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An unprecedented series of 2-imino-1,3-thiazolidin-4-ones were designed by straightforward and dynamic technique via one-pot three-component reaction of isothiocyanatobenzene, primary amines, ethyl bromoacetate and/or phenacylbromide. Furthermore, we found that the reaction between 2-imino-1,-3-thiazolidin-4-one and arylidenemalononitrile using of C 2 H 5 ONa as catalyst gave the corresponding 3-(2-phenylethyl)-5-(4-arylidene)-2-(phenyl imino)-1,-3-thia-zolidin-4-one instead of 5-amino-7-aryl-3-(2-phenylethyl)-2-(phenylimino)-3,7-dihydro-2H-6-carbonitrile. The identical molecules were designed through other routes via the reaction of 2-imino-1,3-thiazolidin-4-one with the corresponding aryl carbaldehyde.

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Anticancer properties of 4-thiazolidinone derivatives depend on peroxisome proliferator-activated receptor gamma (PPARγ)

Cited by 44 publications

References 33 publications

Synthesis, Characterization, Molecular Docking, and Anticancer Evaluation of 4‐Thiazolidinone Analogues

Synthesis, Characterization, Molecular Docking, and Anticancer Evaluation of 4‐Thiazolidinone Analogues

Design, synthesis, and molecular docking studies of thiazolidinediones as PPAR‐γ agonists and thymidylate synthase inhibitors

One‐pot multicomponent designing of novel 2‐imino‐4‐arylidene‐1,3‐thiazolidin‐4‐one

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