Thiazolidinone/thiazole based hybrids – New class of antitrypanosomal agents

Kryshchyshyn, Anna; Kaminskyy, Danylo; Karpenko, Olexandr; Gzella, Andrzej; Grellier, Philippe; Lesyk, Roman

doi:10.1016/j.ejmech.2019.04.052

Cited by 56 publications

(30 citation statements)

References 60 publications

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“…Compounds with a 2-arylindole fragment were more active than 6-arylimidazo [2,1-b][1, 3, 4]thiadiazole analogues. For the compounds without phenyl ring attached to the indole fragment, no significant antitrypanosomal activity was found as well as for the compounds with a C5-ene-fragment in the 4-thiazolidinone core [155].…”

Section: -Thiazolidinone Frame In the Design Of Antitrypanosomalsmentioning

confidence: 94%

“…Development of optimization directions of thiazolidinone-hydrazone structures led to new hybrid molecules bearing thiazolidinone/thiazole and 2-phenylindole/6-phenyl-imidazo[2,1-b][1, 3, 4]thiadiazole cores with hydrazone linkers 19, 20 [155]. Compounds with sub-micromolar levels of trypanocidal activity toward bloodstream forms of T.b.…”

Section: -Thiazolidinone Frame In the Design Of Antitrypanosomalsmentioning

confidence: 99%

“…The main features of the molecular structure of thiazolidinone-hydrazonebased compounds can be outlined as the following: (i) thiazole core (position C4, small aryl or alkyl substituent; C5 position, unsubstituted or small alkyl fragment; N3 position, variety of substituents) or 4-thiazolidinone core (C5 position, unsubstituted or small alkyl fragment); (ii) hydrazone linker in the C2 position of the main core; (iii) additional molecular fragment, diverse substituents (from simple alkyl(aryl)ydene fragment to privileged heterocyclic cores); and (iv) target compounds imitating the thiosemicarbazones with trypanocidal activity [147,153,155].…”

Section: -Thiazolidinone Frame In the Design Of Antitrypanosomalsmentioning

confidence: 99%

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Thiazolidinone-Related Heterocyclic Compounds as Potential Antitrypanosomal Agents

Kryshchyshyn¹,

Kaminskyy²,

Grellier³

et al. 2021

Azoles - Synthesis, Properties, Applications and Perspectives

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Human African trypanosomiasis (HAT) and Chagas disease are neglected tropical diseases (NTDs) due to parasite protists from the Trypanosoma genus transmitted by insect vectors. Trypanosomiases affect mostly poor populations in the developing countries, and the development of new antitrypanosomal drugs is underinvested by governments and the pharmaceutical industry. In this chapter, we described the development of 4-thiazolidinone and thiazole derivatives with heterocyclic fragments which exhibit good inhibition of trypanosome growth and might constitute potential candidates for the development of new drugs against trypanosomiasis. Antitrypanosomal design, mainly within structure-based design, led to the synthesis of 5-ene-4-thiazolidinone-3-alkanecarboxylic acids; 2,3-disubstituted 4-thiazolidinones; thiazolidinone-pyrazoline, phenylindole-thiazolidinone, and imidazothiadiazole-thiazolidinone hybrids; as well as 4-thiazolidinone-based fused heterocycles, especially thiopyrano[2,3-d]thiazoles, and non-thiazolidinone compounds-namely, isothiocoumarine derivatives. Moreover, antitrypanosomal 4-thiazolidinones are of special interest in the search for new antimalarial and antileishmanial agents. Also many active anticancer agents among the abovementioned 4-thiazolidinones have been discovered.

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Section: -Thiazolidinone Frame In the Design Of Antitrypanosomalsmentioning

confidence: 94%

Section: -Thiazolidinone Frame In the Design Of Antitrypanosomalsmentioning

confidence: 99%

Section: -Thiazolidinone Frame In the Design Of Antitrypanosomalsmentioning

confidence: 99%

See 1 more Smart Citation

Thiazolidinone-Related Heterocyclic Compounds as Potential Antitrypanosomal Agents

Kryshchyshyn¹,

Kaminskyy²,

Grellier³

et al. 2021

Azoles - Synthesis, Properties, Applications and Perspectives

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“…These derivatives have also been used as sensitive analytical reagents. 4-Thiazolidone motif is considered as privileged scaffolds in medicinal chemistry and is currently the subject of extensive research [2][3][4][5][6][7][8][9][10][11][12].…”

Section: Introductionmentioning

confidence: 99%

Synthesis antimicrobial and antitumor activities of 2-[5-(2-R-benzyl)thiazol-2-ylimino]thiazolidin-4-ones

2020

Biointerface Res Appl Chem

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By the reaction of N-(5-R-benzyl-thiazol-2-yl)-2-chloroacetamides with potassium thiocyanate were synthesized 2-[5-(2-R-benzyl)thiazol-2-ylimino]thiazolidin-4-ones. The structures of target compounds 9a-e were confirmed by using NMR spectroscopy and elemental analysis. The antimicrobial and anticancer activity of synthesized compounds was evaluated. The compounds with high antimicrobial activity against Staphylococcus aureus ATCC 43300 were identified.

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“…The synthesized conjugates were evaluated for their antiplasmodial activity against the CQ-resistant P.falciparum FcB1/Colombia strain, according to published procedure. 27,28 The cytotoxicity of the compounds was evaluated using the primary human fibroblast cell line AB943, also according to published procedure, 29 which allowed the calculation of their selectivity index (SI). In…”

mentioning

confidence: 99%

Synthesis of Novel G Factor or Chloroquine-Artemisinin Hybrids and Conjugates with Potent Antiplasmodial Activity

Pepe

Toumpa

André-Barrès

et al. 2020

ACS Med. Chem. Lett.

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A series of novel hybrids of artemisinin (ART) with either a phytormone endoperoxide G factor analogue (GMeP) or chloroquine (CQ) and conjugates of the same compounds with the polyamines (PAs) spermidine (Spd) and homospermidine (Hsd) were synthesized and their antimalarial activity were evaluated using the CQ-resistant P. falciparum FcB1/Colombia strain. The ART-GMeP hybrid 5 and compounds 9 and 10 which are conjugates of Spd and Hsd with two molecules of ART, and one molecule of GMeP, were the most potent with IC50 values of 2.6, 8.4 and 10.6 nM, respectively. The same compounds also presented the highest selectivity indexes against the primary human fibroblast cell line AB943 ranging from 16,372 for the hybrid 5 to 983 for the conjugate 10 of Hsd.

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Thiazolidinone/thiazole based hybrids – New class of antitrypanosomal agents

Cited by 56 publications

References 60 publications

Thiazolidinone-Related Heterocyclic Compounds as Potential Antitrypanosomal Agents

Thiazolidinone-Related Heterocyclic Compounds as Potential Antitrypanosomal Agents

Synthesis antimicrobial and antitumor activities of 2-[5-(2-R-benzyl)thiazol-2-ylimino]thiazolidin-4-ones

Synthesis of Novel G Factor or Chloroquine-Artemisinin Hybrids and Conjugates with Potent Antiplasmodial Activity

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