Syntheses and evaluation of antioxidant activity of sydnonyl substituted thiazolidinone and thiazoline derivatives

Shih, Ming Chang; Ke, Fang-Ying

doi:10.1016/j.bmc.2004.06.033

Cited by 245 publications

(103 citation statements)

References 31 publications

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“…On the other hand, sydnones bearing 4-oxothiazolidine (LIII) were less active. The absence of N-H group rendered the latter to be a weak scavenger [78,79]. …”

Section: Antioxidant Activitymentioning

confidence: 99%

Mesoionic Sydnone: A Review in Their Chemical and Biological Properties

Abdualkader

Taher

Yusoff

2017

Int J Pharm Pharm Sci

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Various literature sources have documented sydnones as important molecules with exclusive chemical properties and a wide spectrum of bioactivities. Sydnone can be defined as a five-membered pseudo-aromatic heterocyclic molecule. Classically, 1,2,3-oxadiazole forms the main skeleton of sydnone. The molecule has delocalized balanced positive and negative charges. The five annular atoms share the positive charge and the enolate-like exocyclic oxygen atom bears the negative charge. The hydrogen atom at the position C4 was proved to have acidic and nucleophilic functionalities making the sydnone ring reactive towards electrophilic reagents. These unique chemical features enable sydnones to interact with biomolecules resulting in important therapeutic effects like anticancer, antidiabetic, antimicrobial, antioxidant and anti-inflammatory. Consequently, we aim from the current article to review the available chemical and pharmacological information on sydnone and its derivatives.

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“…On the other hand, sydnones bearing 4-oxothiazolidine (LIII) were less active. The absence of N-H group rendered the latter to be a weak scavenger [78,79]. …”

Section: Antioxidant Activitymentioning

confidence: 99%

Mesoionic Sydnone: A Review in Their Chemical and Biological Properties

Abdualkader

Taher

Yusoff

2017

Int J Pharm Pharm Sci

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“…Thiazoles are a familiar group of heterocyclic compounds possessing a wide variety of biological activities, and their usefulness as medicines are well established. Thiazole derivatives are reported to exhibit diverse biological activities as antimicrobial [3][4][5], antioxidant [6], antitubercular [7], and anticonvulsant [8], and anticonvulsant, anticancer [9,10] agents. Moreover, many derivatives of thiazoles are used as selective Cyclooxygenase-2 Inhibitors [11], in addition to their use as 5-HT3 receptor antagonists [12] and as potent and selective acetyl Co-A carboxylase-2 inhibitors [13].…”

Section: Chemistrymentioning

confidence: 99%

Synthesis, Characterization and Molecular Docking of Novel Bioactive Thiazolyl-Thiazole Derivatives as Promising Cytotoxic Antitumor Drug

et al. 2015

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Abstract:Reactions of ethylidenethiocarbohydrazide with hydrazonoyl halides gave 1,3-thiazole or 1,3,4-thiadiazole derivatives according to the type of hydrazonoyl halides. Treatment of ethylidenethiosemicarbazide with hydrazonoyl halides and dimethylacetylene dicarboxylate (DMAD) afforded the corresponding arylazothiazoles and 1,3-thiazolidin-4-one derivatives, respectively. The structures of the synthesized products were confirmed by IR, 1 H-NMR, 13 C-NMR and mass spectral techniques. The cytotoxic activity of the selected products against the Hepatic carcinoma cell line (Hepg-2) was determined by MTT assay indicating a concentration dependent cellular growth inhibitory effect, especially for compounds 14c and 14e. The dose response curves indicated the IC 50 (the concentration of test compounds required to kill 50% of cell population) were 0.54 µM and 0.50 µM, respectively. Confocal laser scanning imaging of the treated cells stained by Rhodamin 123 and Acridine orange dyes confirmed that the selected compounds inhibit the mitochondrial lactate dehydrogenase enzymes. The binding mode of the active compounds was interpreted by a molecular docking study. The obtained results revealed promising cytotoxic activity.

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“…13 Stock solution of the drug was d r u g i n v e n t i o n t o d a y 5 ( 2 0 1 3 ) 2 1 6 e2 2 2 diluted to different concentrations in the range of 100e200 mg/ ml in methanol. Methanolic solution of the synthesized compounds (2 ml) was added to 0.003% (w/v) methanol solution of DPPH (1 ml).…”

Section: Antioxidant Activitymentioning

confidence: 99%