In vitro antioxidant activity of thiazolidinone derivatives of 1,3-thiazole and 1,3,4-thiadiazole

Djukić, Mirjana; Fesatidou, Mara; Xenikakis, Iakovos; Geronikaki, Athina; Angelova, Violina T.; Savić, Vladimir; Pasic, Marta; Krilovic, Branislav; Djukić, Dušan Lj.; Gobeljić, Borko; Pavlica, Marina; Djurić, Ana; Stanojević, Ivan; Vojvodić, Danilo; Saso, Luciano

doi:10.1016/j.cbi.2018.03.013

Cited by 107 publications

(65 citation statements)

References 36 publications

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“…Thiosemicarbazones have been reported for their wide spectrum of antibacterial [1], anticancer [2,3], anti-inflammatory and antioxidant activities [4]. On the other hand, the chemical modification of compounds containing 4-thiazolidinone moiety leads to their wide appositeness as efficacious pharmacological agents, paving the way for their discernible antimicrobial [5,6], antimalarial [7], anti-HIV [8], antioxidant [9], anticancer [10][11][12][13], antiarrhythmic [14] and anti-inflammatory [15,16] activities. The array of biological responses exhibited by this coalescence of thiosemicarbazone with 4-thiazolidinone moiety has attracted researchers to further explore the potency of these compounds.…”

Section: Introductionmentioning

confidence: 99%

2-{[(4-Hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl Acetic Acid

Karanth

Narayana

Kodandoor

et al. 2018

Molbank

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Thia-Michael addition of 2-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazine-1-carbothioamide (1) with maleic anhydride results in the formation of the title compound 2-{[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl acetic acid 2. The precursor 1 is synthesized by the reaction of 4-hydroxy-3,5-dimethoxybenzaldehyde and thiosemicarbazide in the presence of glacial acetic acid as the catalyst. The structure of the title compound is determined by elemental analysis, FT-IR, 1H-NMR, 13C-NMR and mass spectral data. In order to determine the molecular interactions with the bacterial enzyme, the title compound is further docked into the active site of the MurB protein of Staphylococcus aureus (PDB ID: 1HSK). The in vitro antibacterial and antifungal activity of the title compound is carried out in order to appraise its antimicrobial efficacy by determination of zone of inhibition and minimal inhibitory concentration. The compound is also evaluated for its antioxidant property by 2,2-diphenyl-1-picryl-hydrazyl (DPPH) radical scavenging assay.

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Section: Introductionmentioning

confidence: 99%

2-{[(4-Hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl Acetic Acid

Karanth

Narayana

Kodandoor

et al. 2018

Molbank

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“…The last years of the research have confirmed that thiazole scaffold has diverse biological properties that can be used to treat many diseases, such as microbial infections (Bikobo et al 2017;Secci et al 2012;Łączkowski et al 2018a, 2018bZaki et al 2018;Ansari et al 2018), Parkinson's disease (Carradori et al 2018), cancer (de Santana et al 2018;Łączkowski et al 2014, 2016a, 2016bPiechowska et al 2019;Gomha et al 2018), epilepsy (Siddiqui and Ahsan 2010;Ahangar et al 2011;Łączkowski et al 2016a, 2016b, toxoplasmosis (Schultz et al 2014;Łączkowski et al 2018a, 2018b, and antioxidants (Geronikaki et al 2013;Djukic et al 2018). Considering the above-mentioned findings, we decided to design and synthesize the structure of hybrids incorporating both the thiazole ring and the cyclohexenyl moiety.…”

Section: Introductionmentioning

confidence: 98%

Synthesis, antimicrobial activity, and determination of the lipophilicity of ((cyclohex-3-enylmethylene)hydrazinyl)thiazole derivatives

et al. 2019

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Synthesis and investigation of antimicrobial activity of fifteen novel thiazoles containing cyclohexene moiety are presented. Among the derivatives, compounds 3a-3d, 3f, 3n, and 3o showed very strong activity against the reference Candida spp. strains with MIC = 0.015-3.91 µg/ml. The activity of these compounds is similar and even higher than the activity of nystatin used as positive control. Compounds 3d, 3f, 3n, 3o showed the highest activity with very strong effect towards most of yeasts isolated from clinical materials with MIC = 0.015-7.81 µg/ml. The cytotoxicity studies for the most active compounds showed that Candida spp. growth was inhibited at noncytotoxic concentrations for the mammalian L929 fibroblast. In addition, a good correlation was obtained between lipophilicity of compounds determined using reversed phase thin-layer chromatography and their antifungal activity.

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“…Tiazepine moiety exhibits important pharmacological properties as antiarrhythmic, antispasmodic, analgesic, anticancer, anti-inflammatory, antidepressive, antidiabetic and antioxidant [2]. Regarding 4-thiazolidinones, many pharmaceutical analogs have the N-C-S bond system in their basic structures and because of this, they are very interesting for studying the hypnotic [3], anticancer [4], antioxidant [5], anti-inflammatory [6], and anti-HIV effects, among others [7].…”

Section: Introductionmentioning

confidence: 99%

“…We have previously study the optimal microwave conditions for the synthetic strategy for the preparation of 4-thiazolidinones (5) starting from 2,3:4,5-di-O-isopropylidene-β-D-arabino-hexos-2ulo-2,6-pyranose (1a), mercaptoacetic acid (2) and different aromatic and heteroaromatic amines (3), under 300 W and 120 °C without solvent (Figure 1) [10]. Depending on the substrate structure, two different type of products could be possible: benzothiazepines (4) and 4-thiazolidinones (5). Under these reaction conditions, only two diastereoisomers corresponding to 1,3-thiazolidin-4-ones in excellent yields (82-97%) were obtained.…”

Section: Introductionmentioning

confidence: 99%

Microwave Assisted Three Component Reaction Conditions to Obtain New Thiazolidinones with Different Heterocyclic Skeletons

Lorenzo

Ocampo

Mandolesi

2019

The 23rd International Electronic Conference on Synthetic Organic Chemistry

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We present here a new proposal for the "one pot" generation of new 4-thiazolidinones (9a-e) through a multicomponent reaction under microwave irradiation conditions, using aromatic and heteroaromatic amines (8a-e), absolute ethanol as a "green" solvent and modifying the aldehyde group in the glycosidic residue, synthesized from D-mannitol. The study is focused in the variation of the irradiation times and the concentration of thioglycolic acid in order to study the possibility of controlling the structure and/or stereochemistry of the products formed in the reaction. Thiazolidinones 9a-d were obtained with a 69-82% The generation of the corresponding reaction products were monitored by TLC and CG-MS, taking reaction aliquots. The conditions reaction proved to be chemoselective depending on the excess of acid and irradiation times.

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In vitro antioxidant activity of thiazolidinone derivatives of 1,3-thiazole and 1,3,4-thiadiazole

Cited by 107 publications

References 36 publications

2-{[(4-Hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl Acetic Acid

2-{[(4-Hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl Acetic Acid

Synthesis, antimicrobial activity, and determination of the lipophilicity of ((cyclohex-3-enylmethylene)hydrazinyl)thiazole derivatives

Microwave Assisted Three Component Reaction Conditions to Obtain New Thiazolidinones with Different Heterocyclic Skeletons

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