3-[5-(1H-Indol-3-ylmethylene)-4-oxo-2-thioxothiazolidin-3-yl]-propionic Acid as a Potential Polypharmacological Agent

Konechnyi, Yulian; Lozynskyi, Andrii; Ivasechko, Iryna; Dumych, Tetiana; Paryzhak, Solomiya; Hrushka, Oksana; Partyka, Ulyana; P., Pasichnyuk, I.; Khyluk, Dmytro; Lesyk, Roman

doi:10.3390/scipharm91010013

Cited by 3 publications

(1 citation statement)

References 26 publications

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“…Thiazolidine derivatives can potentially target cancer cells with altered glucose utilization, leading to metabolic stress and cell death [ 17 ]. Moreover, these compounds exhibit anti-inflammatory properties [ 18 , 19 ], which can suppress tumor-promoting inflammation and contribute to their anticancer activity [ 20 , 21 ].…”

Section: Introductionmentioning

confidence: 99%

Derivatives Incorporating Acridine, Pyrrole, and Thiazolidine Rings as Promising Antitumor Agents

Garberová,

Potočňák,

Tvrdoňová

et al. 2023

Molecules

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Derivatives combining acridine, pyrrole, and thiazolidine rings have emerged as promising candidates in the field of antitumor drug discovery. This paper aims to highlight the importance of these three structural motifs in developing potent and selective anticancer agents. The integration of these rings within a single molecule offers the potential for synergistic effects, targeting multiple pathways involved in tumor growth and progression. Spiro derivatives were efficiently synthesized in a two-step process starting from isothiocyanates and 2-cyanoacetohydrazide. The thiourea side chain in spiro derivatives was utilized as a key component for the construction of the thiazolidine-4-one ring through regioselective reactions with bifunctional reagents, namely methyl-bromoacetate, dietyl-acetylenedicarboxylate, ethyl-2-bromopropionate, and ethyl-2-bromovalerate. These reactions resulted in the formation of a single regioisomeric product for each derivative. Advanced spectroscopic techniques, including 1D and 2D NMR, FT-IR, HRMS, and single-crystal analysis, were employed to meticulously characterize the chemical structures of the synthesized derivatives. Furthermore, the influence of these derivatives on the metabolic activity of various cancer cell lines was assessed, with IC50 values determined via MTT assays. Notably, derivatives containing ester functional groups exhibited exceptional activity against all tested cancer cell lines, boasting IC50 values below 10 μM. Particularly striking were the spiro derivatives with methoxy groups at position 3 and nitro groups at position 4 of the phenyl ring. These compounds displayed remarkable selectivity and exhibited heightened activity against HCT-116 and Jurkat cell lines. Additionally, 4-oxo-1,3-thiazolidin-2-ylidene derivatives demonstrated a significant activity against MCF-7 and HCT-116 cancer cell lines.

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Section: Introductionmentioning

confidence: 99%

Derivatives Incorporating Acridine, Pyrrole, and Thiazolidine Rings as Promising Antitumor Agents

Garberová,

Potočňák,

Tvrdoňová

et al. 2023

Molecules

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The anti‐breast cancer potential of indole/isatin hybrids

Wang,

Huang,

Yuan

et al. 2023

Archiv der Pharmazie

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Breast cancer (BC) is one of the most prevalent malignancies and the major contributor to cancer mortality in women globally, with a high degree of heterogeneity and a dismal prognosis. As drug resistance is responsible for most BC fatalities and advanced BC is currently considered incurable, finding innovative anti‐BC chemotherapeutics is urgently required. Indole and its analog isatin (indole‐1H‐2,3‐dione) are prominent pharmacophores in the development of novel medications, and their derivatives exhibit strong anticancer activities, also against BC. In particular, indole/isatin hybrids exhibit significant potency against BC including multidrug‐resistant forms and excellent selectivity by influencing a variety of biological targets associated with the disease, supplying helpful building blocks for the identification of potential new BC treatment options. This review includes articles from 2020 to the present and provides insights into the in vitro and in vivo anti‐BC potential, molecular mechanisms, and structure–activity relationships (SARs) of indole/isatin hybrids that may be helpful in the development of innovative anti‐BC chemotherapeutics.

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Synthesis of new S-(w-fluoralkyl) 4-substituted benzenesulfonothioates and their antimicrobial activity

Karkhut,

Polovkovych

2024

Vopr. Khim. Khim. Tekhnol.

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New S-(-fluoralkyl) 4-amino- and 4-acetamidobenzenesulfonothioates were synthesized by the reaction of sodium salts of the substituted thiosulfonic acids and corresponding -fluoralkylbromides. The study of their antimicrobial activity against thirteen reference and clinical bacterial and fungal strains using agar diffusion method was conducted. All compounds showed significant antimicrobial activity, two of them showed higher activity against Candida albicans than known antifungal compound of sulfonothioate class, S-ethyl ester of 4-aminobenzenethiosulfonic acid.

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3-[5-(1H-Indol-3-ylmethylene)-4-oxo-2-thioxothiazolidin-3-yl]-propionic Acid as a Potential Polypharmacological Agent

Cited by 3 publications

References 26 publications

Derivatives Incorporating Acridine, Pyrrole, and Thiazolidine Rings as Promising Antitumor Agents

Derivatives Incorporating Acridine, Pyrrole, and Thiazolidine Rings as Promising Antitumor Agents

The anti‐breast cancer potential of indole/isatin hybrids

Synthesis of new S-(w-fluoralkyl) 4-substituted benzenesulfonothioates and their antimicrobial activity

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