Chemistry and Biological Activities of 1,3-Thiazolidin-4-ones

Cúnico, Wilson; Gomes, Cláudia R. B.; Vellasco, Walcimar T.

doi:10.2174/157019308786242232

Cited by 67 publications

(29 citation statements)

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“…[13,14] The main synthesis routes to 4-thiazolidinones involve three components (an aldehyde, an amine or thiosemicarbazide, and mercaptoacetic acid or halogenoester), either in one-or two-step processes. [15][16][17][18][19][20] We report in this article the syntheses of a new class of structurally novel 4-thiazolidinone derivatives, incorporating two known bioactive heterocyclic nuclei such as pyrone and 4-thiazolidinone, known to be active towards (G þ and G -) and yeast. Pyrones and their fused derivatives have attracted a great deal of interest because of their wide range of biological activities.…”

Section: Synthesis and Antimicrobial Activity Evaluation Of Novel 4-tmentioning

confidence: 99%

Synthesis and Antimicrobial Activity Evaluation of Novel 4-Thiazolidinones Containing a Pyrone Moiety

Nechak

Bouzroura

Benmalek

et al. 2014

Synthetic Communications

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A series of thiosemicarbazones 3a-d and 4-thiazolidinones 5a-d, 7a-d, and 9a-h were synthesized and evaluated for their in vitro antimicrobial activity. Condensation of 3-acetyl-4-hydroxy-6-methyl-2H pyran-2-one1 (dehydroacetic acid) with thiosemicarbazide 2a-d in ethanol at room temperature yielded the thiosemicarbazones 3a-d. These compounds were exploited to synthesize the 4-thiazolidinones 5a-d via their reactions with ethyl 2-bromo propionate4. Derivatives 7a-d were prepared by reaction of the thiosemicarbazones 3a-d with phenyl bromoacetate 6. The 4-thiazolidinones 9a-h were obtained by treatment of compound 3a or 3c with maleimide derivatives 8a-d in refluxing ethanol, under sulfuric acid catalysis. All compounds were screened in vitro for their antibacterial and antifungal activities against five human pathogens microorganisms: Escherichia coli ATCC 25992, Pseudomonas aeruginosa ATCC 27852, Staphylococcus aureus ATCC 43300, Staphylococcus aureus ATCC 25923, and Candida albicans.

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Section: Synthesis and Antimicrobial Activity Evaluation Of Novel 4-tmentioning

confidence: 99%

Synthesis and Antimicrobial Activity Evaluation of Novel 4-Thiazolidinones Containing a Pyrone Moiety

Nechak

Bouzroura

Benmalek

et al. 2014

Synthetic Communications

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“…It is well documented that benzophenone nucleus is associated with a variety of pharmacological actions . This diversity in the biological response profile has attracted the attention of many researchers to explore benzophenones integrated thiazolidinone skeleton towards multiple potential biological activities . Recent studies have revealed that the burden of gout is increasing worldwide and more research is focused on synthesis of heterocyclic analogs as XOI as well as antioxidants.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Xanthine Oxidase Inhibition, and Antioxidant Screening of Benzophenone Tagged Thiazolidinone Analogs

Ranganatha

Begum

Naveen

et al. 2014

Archiv der Pharmazie

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A series of novel 2-(diaryl methanone)-N-(4-oxo-2-phenyl-thiazolidin-3-yl)-acetamides were synthesized by various Schiff bases of (4-benzoyl-phenoxy)-aceto hydrazide with thioglycolic acid. The structures of the newly synthesized compounds were confirmed by IR, (1) H NMR, mass spectra, and C, H, N analysis. Further, all the synthesized compounds 9a-n were evaluated for xanthine oxidase (XO) inhibition and antioxidant properties. Among all the tested compounds, 9f, 9m, and 9n demonstrated potent XO inhibition of 52, 76, and 26%, respectively, compared to the standard drug allopurinol, which is evident from in vitro and in silico analysis. On the other hand, compounds 9c, 9d, and 9k exhibit potent antioxidant properties.

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“…Thiazolidinones are important five-membered heterocycles that have valuable biological activities in the medicine chemistry 1 . Recently, we published an efficient, solvent free improved synthesis of 2-(alkyl/aryl)-3-arylamino-1,3 thiazolidin-4-ones from hydrazones.…”

Section: Introductionmentioning

confidence: 99%