Antitubercular properties of thiazolidin-4-ones – A review

Trotsko, Nazar

doi:10.1016/j.ejmech.2021.113266

Cited by 49 publications

(25 citation statements)

References 75 publications

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“…However, thiazolidinone derivatives belong to the most frequently studied moieties and its presence in penicillin was the first recognition of its occurrence in nature [15]. Thiazo-and selenazolidine-4-ones are an important class of compounds in organic and medicinal chemistry [16][17]. The 4-thiazolidinone or 4selenazolidinone ring system is a core structure in various synthetic pharmaceutical agents, displaying a broad spectrum of biological activities such as antitubercular, antibacterial, anti-inflammatory, antioxidant agents, antiviral agents, especially as anti-HIV agents, and their use as anticancer drugs [13,[18][19][20].…”

Section: Sulfonamidesmentioning

confidence: 99%

Synthesis, Antimicrobial, Antioxidant, Toxicity and Anticancer Activity of a New Azetidinone, Thiazolidinone and Selenazolidinone Derivatives Based on Sulfonamide

2022

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A new series of azetidinone (Z2a-Z2e, Z2g), thiazolidinone and selenazolidinone derivatives (Z2B, Z2E, Z2B', Z2E') based on sulfonamide have been synthesized and characterized by different instrumental techniques, such as elemental analyses, FTIR, multinuclear NMR (1H, 13C) and mass spectrometry. The tested compound containing selenium (Z2E') was less toxic than its analogs containing sulfur (Z2E) based on the LD50 value determined by Dixon's up and down method. All compounds showed antibacterial properties, however, Z2E' was more active against Gram-negative bacteria: Escherichia coli and Pseudomonas aeruginosa than Gram-positive ones: Streptococcus aureus and Bacillus, with the lowest MIC value of 5 mg/mL. All compounds showed good antioxidant activity at a lower rate than the standard compound BHT (82%). More precisely, Z2b was the main compound that possess strong activity as an antioxidant (73%). MTT viability assay showed that all tested compounds had cytotoxic effects on MCF-7 cells after 72 h of treatment. Our results revealed that Z2E' and Z2E compounds possessed strong activity (IC50 = 24.8 and 90.9 µg/mL, respectively) against MCF-7 cells at a higher rate than the standard compound 5-FU (IC50 = 97.47 µg/mL). Our results indicated that Z2E' had a promising bioactive scaffold of great medicinal interest due to their numerous pharmacological and biological activities.

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Section: Sulfonamidesmentioning

confidence: 99%

Synthesis, Antimicrobial, Antioxidant, Toxicity and Anticancer Activity of a New Azetidinone, Thiazolidinone and Selenazolidinone Derivatives Based on Sulfonamide

2022

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“…Our interest is focused on rhodanine (2-sulfanylidene-1,3-thiazolidin-4-one) derivatives, which were synthesized in our laboratory and tested for their biological activities [ 9 , 10 , 11 , 12 , 13 ]. Derivatives of rhodanine show a broad spectrum of biological activities, e.g., antibacterial, antifungal, antitubercular, anticancer, antidiabetic, anti-inflammatory and antiparasitic activities [ 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 ]. Given the high potency of rhodanine derivatives as bioactive agents, we have evaluated cinnamylidene derivatives of rhodanine towards their anthelmintic activity.…”

Section: Introductionmentioning

confidence: 99%

Discovery of Cinnamylidene Derivative of Rhodanine with High Anthelmintic Activity against Rhabditis sp.

et al. 2022

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The treatment of parasitic infections requires the application of chemotherapy. In view of increasing resistance to currently in-use drugs, there is a constant need to search for new compounds with anthelmintic activity. A series of 16 cinnamylidene derivatives of rhodanine, including newly synthesized methoxy derivatives (1–11) and previously obtained chloro, nitro, and diethylamine derivatives (12–16), was investigated towards anthelmintic activity. Compounds (1–16) were evaluated against free-living nematodes of the genus Rhabditis sp. In the tested group of rhodanine derivatives, only compound 2 shows very high biological activity (LC50 = 0.93 µg/µL), which is higher than the reference drug albendazole (LC50 = 19.24 µg/µL). Crystal structures of two compounds, active 2 and inactive 4, were determined by the X-ray diffraction method to compare molecular geometry and search for differences responsible for observed biological activity/inactivity. Molecular modelling and selected physicochemical properties prediction were performed to assess the potential mechanism of action and applied in the search for an explanation as to why amongst all similar compounds only one is active. We can conclude that the tested compound 2 can be further investigated as a potential anthelmintic drug.

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“…1,3,4-Thiadiazoles have a wide range of pharmacological activities such as; anti-bacterial [11], antimalarial, anti-microbial, anti-oxidant [12], anti-convulsant [13], anti-parasitic [14], anti-tuberculosis [15], antileishmanial [16], anti-inflammatory [17] and anti-cancer agents [18]. Also, 4-thiazolidinones exhibit distinct biological activities such as; anti-inflammatory [19], antimicrobial [20], anti-diabetic [21], anti-tuberculosis [22] and anti-cancer [23]. On the other hand, heterocyclic compounds with fivemembered rings containing three nitrogen atoms such as 1,2,4-triazoles play an important critical role in the structural elucidation of various natural products [24] and they are able to form hydrogen bonds with suitable targets leading to improve pharmacokinetics, pharmacological, and toxicological properties [25].…”

Section: Introductionmentioning

confidence: 99%

Untitled

2022

Sohag J. Sci

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In this work we studied the reaction of carbohydrazides with some reagents having electrophilic centers such as arylmethylenemalononitrile, aromatic aldehydes, bis(methylthio)methylenemalononitrile, dimethyl acetylene-dicarboxylate and cyanoguanidine. The resulting products are five-membered heterocyclic rings such as thiadiazoles, thiazoles, triazoles; and six-membered heterocyclic rings such as triazines.

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Antitubercular properties of thiazolidin-4-ones – A review

Cited by 49 publications

References 75 publications

Synthesis, Antimicrobial, Antioxidant, Toxicity and Anticancer Activity of a New Azetidinone, Thiazolidinone and Selenazolidinone Derivatives Based on Sulfonamide

Synthesis, Antimicrobial, Antioxidant, Toxicity and Anticancer Activity of a New Azetidinone, Thiazolidinone and Selenazolidinone Derivatives Based on Sulfonamide

Discovery of Cinnamylidene Derivative of Rhodanine with High Anthelmintic Activity against Rhabditis sp.

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