Thiopyrano[2,3-d]Thiazoles as New Efficient Scaffolds in Medicinal Chemistry

Kryshchyshyn, Anna; Roman, Olexandra; Lozynskyi, Andrii; Lesyk, Roman

doi:10.3390/scipharm86020026

Cited by 42 publications

(23 citation statements)

References 59 publications

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“…So, various thiopyranothiazoles serve as a fruitful source of drug-like molecules that, unlike their precursors 5-ylidene-4-thiazolidinones, cannot be claimed as PAINS [99]. This class of fused thiazolidinone derivatives is characterized by a number of different biological activities [158], the most studied being the antitumor activity [96,157,159,160]. Recently, antiparasitic properties of these polycyclic compounds have been also reported.…”

Section: Fused Heterocyclic Molecules Based On the Core 4-thiazolidinonementioning

confidence: 99%

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: Fused Heterocyclic Molecules Based On the Core 4-thiazolidinonementioning

confidence: 99%

Thiazolidinone-Related Heterocyclic Compounds as Potential Antitrypanosomal Agents

Kryshchyshyn¹,

Kaminskyy²,

Grellier³

et al. 2021

Azoles - Synthesis, Properties, Applications and Perspectives

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“…It has been revealed that compounds containing thiazole skeleton exhibit significant biological activities, which have pulled in consideration of researchers in both medicinal chemistry and chemical biology. In the domain of science, the thiazole skeleton is a key pharmacophore because of its ubiquity in a variety of biological properties . Few noteworthy examples of thiazole derivatives are depicted in Figure .…”

Section: Introductionmentioning

confidence: 99%

“…In the domain of science, the thiazole skeleton is a key pharmacophore because of its ubiquity in a variety of biological properties. [3][4][5][6][7][8][9][10] Few noteworthy examples of thiazole derivatives are depicted in Figure 1. Besides, the hydrazinylthiazolyl core is one of the important organic structures which have produced a profound interest in medicinal and industrial researchers.…”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis, Antibacterial, Antifungal, Antioxidant and Cytotoxicity Study of 2‐(2‐Hydrazineyl)thiazole Derivatives

Adole

Jagdale

et al. 2020

ChemistrySelect

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In the present investigation, an alluring green PEG‐400 mediated one‐pot synthesis of novel 2‐(2‐hydrazinyl)thiazole derivatives from 1,2,6,7‐tetrahydro‐8H‐indeno[5,4‐b]furan‐8‐one has been unveiled via a novel synthetic pathway. The application of PEG in organic reactions as a reaction media is one of the fantastic tools of green chemistry as reactions can be carried out under generous conditions limiting environmental peril and chemical waste. PEG‐400 is recognized as a low‐cost, non‐flammable, environmentally benign, recyclable, and richly available green solvent. A series of novel 2‐(2‐hydrazineyl)thiazole derivatives have been synthesized in good to excellent yield by using the green capability of PEG‐400 solvent. These newly synthesized compounds were tested for their antimicrobial and antioxidant activities. The results revealed that these compounds show good activities compared with the standard. Additionally, all the synthesized compounds exhibit negligible cytotoxicity as compared to the positive control. The structures of all novel compounds reported herein are established using FT‐IR, 1H NMR, 13C NMR, D2O exchange experiment and HRMS techniques.

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“…In contrast, fused derivatives of 5-ene-4-thiazolidinones, namely thiopyranothiazoles retain the pharmacological profile of starting thiazolidinones and are apparently devoid of Michael acceptor functionality, constituting promising scaffolds for the development of antiparasitic agents. Earlier-established anticancer activity of isothiochromenothiazoles [27] and related thiopyranothiazoles [28][29][30] became one more argument for the study of their antitrypanosomal activity. Anticancer drugs such as bortezomib, aclarubicin, doxorubicin, and mitoxantrone were studied towards Trypanosoma brucei showing trypanocidal activities comparable to those of commercial antitrypanosomal drugs [31,32] within repurposing strategy.…”

Section: Introductionmentioning

confidence: 99%

Isothiochromenothiazoles—A Class of Fused Thiazolidinone Derivatives with Established Anticancer Activity That Inhibits Growth of Trypanosoma brucei brucei

et al. 2018

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Recently, thiazolidinone derivatives have been widely studied as antiparasitic agents. Previous investigations showed that fused 4-thiazolidinone derivatives (especially thiopyranothiazoles) retain pharmacological activity of their synthetic precursors—simple 5-ene-4-thiazolidinones. A series of isothiochromeno[4a,4-d][1,3] thiazoles was investigated in an in vitro assay towards bloodstream forms of Trypanosoma brucei brucei. All compounds inhibited parasite growth at concentrations in the micromolar range. The established low acute toxicity of this class of compounds along with a good trypanocidal profile indicates that isothiochromenothiazole derivatives may be promising for designing new antitrypanosomal drugs.

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Thiopyrano[2,3-d]Thiazoles as New Efficient Scaffolds in Medicinal Chemistry

Cited by 42 publications

References 59 publications

Thiazolidinone-Related Heterocyclic Compounds as Potential Antitrypanosomal Agents

Thiazolidinone-Related Heterocyclic Compounds as Potential Antitrypanosomal Agents

Efficient Synthesis, Antibacterial, Antifungal, Antioxidant and Cytotoxicity Study of 2‐(2‐Hydrazineyl)thiazole Derivatives

Isothiochromenothiazoles—A Class of Fused Thiazolidinone Derivatives with Established Anticancer Activity That Inhibits Growth of Trypanosoma brucei brucei

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