Synthesis and anticancer activity evaluation of 3-(4-oxo-2-thioxothiazolidin-5-yl)-1<i>H</i>-indole-carboxylic acids derivatives

Kryshchyshyn‐Dylevych, Anna; Garazd, M. M.; Karkhut, Andriy; Polovkovych, Svyatoslav; Lesyk, Roman

doi:10.1080/00397911.2020.1786124

Cited by 14 publications

(12 citation statements)

References 24 publications

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“…4-Thiazolidinones Les-3166 [ 18 ], Les-6009 [ 67 ] Les-6166 [ 28 ], and thiopyranothiazole derivative Les-5935 [ 28 ] were synthesised according to previously developed methods. The chemical structures of 4-TZD are presented in Figure 1 .…”

Section: Methodsmentioning

confidence: 99%

Evaluation of Anticancer and Antibacterial Activity of Four 4-Thiazolidinone-Based Derivatives

Skóra

Lewińska

Kryshchyshyn‐Dylevych

et al. 2022

Molecules

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Heterocycles are commonly known for their unique features, e.g., antibacterial or anticancer properties. Although many synthetic heterocycles, such as 4-thiazolidinone (4-TZD), have been synthesized, their potential applications have not yet been fully investigated. However, many researchers have reported relevant results that can be a basis for the search for new potential drugs. Therefore, the aim of this study was to evaluate the cytotoxic, cytostatic, and antibacterial effects of certain 4-thiazolidinone-based derivatives, Les-3166, Les-5935, Les-6009, and Les-6166, on human fibroblasts (BJ), neuroblastoma (SH-SY5Y), epithelial lung carcinoma (A549), and colorectal adenocarcinoma (CACO-2) cell lines in vitro. All tested compounds applied in a concentration range from 10 to 100 µM were able to decrease metabolic activity in the BJ, A549, and SH-SY5Y cell lines. However, the action of Les-3166 was mainly based on the ROS-independent pathway, similarly to Les-6009. In turn, Les-5935 and Les-6166 were able to promote ROS production in BJ, A549, and SH-SY5Y cells, compared to the control. Les-3166, Les-6009, and Les-6166 significantly increased the caspase-3 activity, especially at the concentrations of 50 µM and 100 µM. However, Les-5935 did not induce apoptosis. Only Les-5935 showed a minor cytostatic effect on SH-SY5Y cells. Additionally, the antibacterial properties of the tested compounds against P. aeruginosa bacterial biofilm can be ranked as follows: Les-3166 > Les-5935 > Les-6009. Les-6166 did not show any anti-biofilm activity. In summary, the study showed that Les-5935, Les-6009, and Les-6166 were characterized by anticancer properties, especially in the human lung cancer cell. In cases of BJ, SH-SY5Y, and CACO-2 cells the anticancer usage of such compounds is limited due to effect visible only at 50 and 100 µM.

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Section: Methodsmentioning

confidence: 99%

Evaluation of Anticancer and Antibacterial Activity of Four 4-Thiazolidinone-Based Derivatives

Skóra

Lewińska

Kryshchyshyn‐Dylevych

et al. 2022

Molecules

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“…As a result, compound 119 was active in the concentration range of 0.02‐0.09 μM towards fourteen cancer cell lines such as K‐562, NCI−H‐460, NCI−H522, HCT‐116, HTC‐15, SW‐620, SNB‐75, SF 539, M14, MDA‐MB‐435, OVCAR‐3, NCI/ADR‐RES, ACNH, RXF 393 and HS 578 T. Replacing F with OCH 3 in structurally similar derivatives decreases the anticancer activity. Similarly, the transition from rhodanine derivatives to 9 H ‐thiopyrano[3,4‐ b ]indoles resulted in complete activity loss [33] …”

Section: Pharmacological Significance and Sarmentioning

confidence: 99%

“…Similarly, the transition from rhodanine derivatives to 9H-thiopyrano[3,4-b]indoles resulted in complete activity loss. [33] Toumi and co-workers have synthesized a novel series 122-140 of rhodanine-fused spiro[pyrrolidine-2,3'-oxindoles] by the one-pot three components [3 + 2] cycloaddition of stabilized azomethines (Figure 20). Synthesized compounds have four contiguous stereocenters and excellent regio-and diastereoselectivities.…”

Section: Pharmacological Significance and Sarmentioning

confidence: 99%

Rhodanine‐Incorporated Indole Derivatives as Pharmacologically Vital Hybrids

2022

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Nowadays, some life-threatening diseases keep individuals living in fear of death and experiencing health losses that were before unexpected. Therefore, there is an urgent need for the development of active pharmacological agents to minimize the injurious effect of such diseases. For that, numerous heterocyclic compounds and their hybrids have been designed, developed, and synthesized. They are also considered to be more effective against microorganisms that have developed multi-drug resistance. 2-Thioxo-4-thiazolidinone (rhodanine) and indole are regarded as advantageous heterocycles in medicinal chemistry. The pharmacological properties of rhodanine scaffolds can be improved by incorporating indole moieties. The present review expresses the pharmacological advances of rhodanine-incorporated indole derivatives along with their structure-activity relationships (SAR). To find novel drugs and combat serious diseases, we have observed that such hybrid structures are more effective pharmacophores than single motifs.

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“…For example, new protocols for the synthesis of 3-difluoroalkyl phthalides [1], 3-benzylphthalides [2], 3-(1 -indolyl)phthalides [3], and electrochemical protocol for isoindolinones [4] were developed. Syntheses of (+)-Rubellin C [5], benzo[f]pyrrolo [1, 2-a] [1,4] diazepines [6], fluorinated isocoumarines [7], furo [2,3-d]pyridazines [8], furo [3,4-c]pyridines [9], 1-oxo-9H-thiopyrano [3,4-b]indoles [10], pyrazoloisoindoles [11], phthalazines [12] and isothiocoumarines [13] were studied. ortho-Formyl acids were used for the synthesis of biologically active compounds with anticancer potential [14]; PROTACs E3 ubiquitin ligase inhibitor [15] and MDM2 [16] degrades; STING [17] and PKM2 [18] modulators; inhibitors of Eg5 [19], SIRT1 and SIRT2 [20], 15lipoxygenase-1 [21] and pyruvate kinase activators [22].…”

Section: Introductionmentioning

confidence: 99%

Ethyl 5-Formyl-1-(pyridin-3-yl)-1H-1,2,3-triazole-4-carboxylate: Synthesis, Crystal Structure, Hirshfeld Surface Analysis, and DFT Calculation

Pokhodylo

Slyvka

Goreshnik

et al. 2022

Molbank

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For the first time, 5-formyl-1-(pyridin-3-yl)-1H-1,2,3-triazole-4-carboxylate was synthesized via a two-step scheme. The molecular structure of the compound was determined by a single-crystal X-ray diffraction analysis. The Hirshfeld surface analysis was used to study various intermolecular interactions. The crystalline structure is marked by the presence of three types of π-interactions (n→π*, lp···π, and π···π) between the -C(H)=O group and triazole rings. The compound is a versatile polyfunctional building block for construction of annulated 1,2,3-triazoles.

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Synthesis and anticancer activity evaluation of 3-(4-oxo-2-thioxothiazolidin-5-yl)-1H-indole-carboxylic acids derivatives

Cited by 14 publications

References 24 publications

Evaluation of Anticancer and Antibacterial Activity of Four 4-Thiazolidinone-Based Derivatives

Evaluation of Anticancer and Antibacterial Activity of Four 4-Thiazolidinone-Based Derivatives

Rhodanine‐Incorporated Indole Derivatives as Pharmacologically Vital Hybrids

Ethyl 5-Formyl-1-(pyridin-3-yl)-1H-1,2,3-triazole-4-carboxylate: Synthesis, Crystal Structure, Hirshfeld Surface Analysis, and DFT Calculation

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