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Abstract
Some new sydnonyl-substituted thiazolidine derivatives were synthesized in high yields by the modified Knoevenagel condensation of 3-aryl-4-formylsydnones with thiazolidine-2,4-dione and 2-thioxo-thiazolidine-4-one, respectively. All the synthesized thiazolidine derivatives were screened by paper-disc method to identify their antimicrobial activities against three bacteria viz. Staphylococcus aureus, Proteus vulgaris and Escherichia coli, and two fungal cultures viz. Aspergillus niger and Penicillium citrinum. The reference drugs were Norfloxacin and Griseofulvin, respectively. The screening data indicated that the tested sydnonyl-substituted thiazolidine derivatives exhibited no obvious antibacterial activity compared with the standard drug Norfloxacin. However, thiazolidine derivatives displayed significant antifungal activities against Penicillium citrinum and Aspergillus niger. Notably, all of the tested compounds showed growth inhibitory activity 1.5-4.4 times higher than that of the standard drug Griseofulvin against the two fungi.
Highlights
Thiazolidines, thiazolidinones and their derivatives have attracted continuing interest over the years because of their varied biological activities, such as antitumor [1,2,3], anticancer [4,5,6], anti-inflammatory [7], antimicrobial [8,9,10] and anti-Toxoplasma gondii activities [11]
All the synthesized thiazolidinone derivatives 4a–d, 5a–d were screened by paper-disc method to identify their antimicrobial activities against three bacteria viz. Staphylococcus aureus, Proteus vulgaris and Escherichia coli, and two fungal cultures viz. Aspergillus niger and
The Knoevenagel condensations were controlled at low temperature by successive addition of glacial acetic acid, methylene compounds with piperidine to the sydnone ethanol solution in order
Summary
Thiazolidines, thiazolidinones and their derivatives have attracted continuing interest over the years because of their varied biological activities, such as antitumor [1,2,3], anticancer [4,5,6], anti-inflammatory [7], antimicrobial [8,9,10] and anti-Toxoplasma gondii activities [11]. 3-Aryl-4-formylsydnones 1 have extensively been studied since their discovery [17]. Syntheses of sydnone derivatives substituted with thiazolidine or thiazolidinone group at a suitable position by a convenient method is an important part of developing new and potentially biologically active compounds. 3-aryl-4-formylsydnones 1a–d with thiazolidine-2,4-dione (2) and 2-thioxo-thiazolidin-4-one (3), respectively. All the synthesized thiazolidinone derivatives 4a–d, 5a–d were screened by paper-disc method to identify their antimicrobial activities against three bacteria viz. Staphylococcus aureus, Proteus vulgaris and Escherichia coli, and two fungal cultures viz. Aspergillus niger and Penicillium citrinum
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