Synthesis and antimicrobial activity of some new N-(aryl-oxo-alkyl)-5-arylidene-thiazolidine-2,4-diones

Stana, Anca; Tiperciuc, Brîndușa; Duma, Mihaela; Pı̂rnău, Adrian; Vérité, Philippe; Oniga, Ovidiu

doi:10.2298/jsc130114078s

Cited by 5 publications

(3 citation statements)

References 13 publications

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“…The intermediate parent (compound 3 ) was obtained by N-alkylation in alkaline environment, using dimethylformamide as reaction medium, of thiazolidine-2,4-dione (compound 1 ), via its potassium salt obtained in situ. The protocol used was based on some modified methods that were previously reported in the literature [25,26].…”

Section: Resultsmentioning

confidence: 99%

New Phenolic Derivatives of Thiazolidine-2,4-dione with Antioxidant and Antiradical Properties: Synthesis, Characterization, In Vitro Evaluation, and Quantum Studies

et al. 2019

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Oxidative stress has been incriminated in the physiopathology of many diseases, such as diabetes, cancer, atherosclerosis, and cardiovascular and neurodegenerative diseases. There is a great interest in developing new antioxidants that could be useful for preventing and treating conditions for which oxidative stress is suggested as the root cause. The thiazolidine-2,4-dione derivatives have been reported to possess various pharmacological activities and the phenol moiety is known as a pharmacophore in many naturally occurring and synthetic antioxidants. Twelve new phenolic derivatives of thiazolidine-2,4-dione were synthesized and physicochemically characterized. The antioxidant capacity of the synthesized compounds was assessed through several in vitro antiradical, electron transfer, and Fe2+ chelation assays. The top polyphenolic compounds 5f and 5l acted as potent antiradical and electron donors, with activity comparable to the reference antioxidants used. The ferrous ion chelation capacity of the newly synthesized compounds was modest. Several quantum descriptors were calculated in order to evaluate their influence on the antioxidant and antiradical properties of the compounds and the chemoselectivity of the radical generation reactions has been evaluated. The correlation with the energetic level of the frontier orbitals partially explained the antioxidant activity, whereas a better correlation was found while evaluating the O–H bond dissociation energy of the phenolic groups.

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Section: Resultsmentioning

confidence: 99%

New Phenolic Derivatives of Thiazolidine-2,4-dione with Antioxidant and Antiradical Properties: Synthesis, Characterization, In Vitro Evaluation, and Quantum Studies

et al. 2019

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“…Thiazoles, in general, and their derivatives, thiazolin-4-ones, in particular, are an important class of heterocyclic compounds, with a remarkable medicinal value. They have been associated with a large variety of significant pharmacological activities, such as antifungal 1–3 , antibacterial 4 , 5 , antitumor 3 , 4 , 6 , antiviral 7 , antioxidant 6 , 8 , neuroprotective 9 , analgesic, anti-inflammatory 4 , 10 and anticonvulsant 9 .…”

Section: Introductionmentioning

confidence: 99%

Antioxidant activity and antibacterial evaluation of new thiazolin-4-one derivatives as potential tryptophanyl-tRNA synthetase inhibitors

Stana

Vodnar

Marc

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

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The rapid emergence of bacterial resistance to antibiotics currently available for treating infectious diseases requires effective antimicrobial agents with new structural profiles and mechanisms of action. Twenty-three thiazolin-4-one derivatives were evaluated for their antibacterial activity by determining the growth inhibition zone diameter, the minimum inhibitory concentration (MIC), and the minimum bactericidal concentration (MBC), against gram-positive and gram-negative bacteria. Compounds 3a–c , 3e–h , 6b–c and 9a–c expressed better MIC values than moxifloxacin, against Staphylococcus aureus . Compounds 3h and 9b displayed similar effect to indolmycin, a tryptophanyl-tRNA ligase inhibitor. Due to their structural analogy to indolmycin, all compounds were subjected to molecular docking on tryptophanyl-tRNA synthetase. Compounds 3a–e , 6a–e , 8 and 9a–e exhibited better binding affinities towards the target enzymes than indolmycin. The antioxidant potential of the compounds was evaluated by four spectrophotometric methods. Thiazolin-4-ones 3e , 6e and 9e presented better antiradical activity than ascorbic acid, trolox and BHT, used as references.

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“…All compounds considered had as a common denominator one or two C=O groups, directly located on the thiazoline of thiazolidine nucleus ( fig. 1) [5][6][7][8][9][10][11][12][13]. Other molecular fragments preserved were chosen considering their ability to fit into a quasi-similar pattern.…”

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Rational Synthesis of Some New para-Aminobenzoic Acid Hybrids with Thiazolidin-2,4-diones with Antimicrobial Properties. ADMET and molecular docking evaluation

Marc¹,

Oniga²,

Pı̂rnău³

et al. 2019

Rev. Chim.

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The present paper presents the synthesis, physicochemical characterization, in vitro antimicrobial activity and the molecular docking study of a series of ten new thiazolidine-2,4-dione derivatives conjugated to para-aminobenzoic acid (PABA). The lipophilicity of the new molecules was evaluated in silico. Quantitative elemental C, H, N, S analysis and spectral data (mass spectrometry, infrared and nuclear magnetic resonance) were consistent with the expected data. The results of the antimicrobial activity screening revealed that some of the synthesized compounds had moderate to good activity against E. coli ATCC 25922, S. aureus, ATCC 6538P and C. albicans ATCC 10231.

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Synthesis and antimicrobial activity of some new N-(aryl-oxo-alkyl)-5-arylidene-thiazolidine-2,4-diones

Cited by 5 publications

References 13 publications

New Phenolic Derivatives of Thiazolidine-2,4-dione with Antioxidant and Antiradical Properties: Synthesis, Characterization, In Vitro Evaluation, and Quantum Studies

New Phenolic Derivatives of Thiazolidine-2,4-dione with Antioxidant and Antiradical Properties: Synthesis, Characterization, In Vitro Evaluation, and Quantum Studies

Antioxidant activity and antibacterial evaluation of new thiazolin-4-one derivatives as potential tryptophanyl-tRNA synthetase inhibitors

Rational Synthesis of Some New para-Aminobenzoic Acid Hybrids with Thiazolidin-2,4-diones with Antimicrobial Properties. ADMET and molecular docking evaluation

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