A Facile Synthesis and Antimicrobial Activity Evaluation of Sydnonyl-Substituted Thiazolidine Derivatives

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.

Synthesis and Antifungal Screening of 2-{[1-(5-Alkyl/arylalkylpyrazin-2-yl)ethylidene]hydrazono}-1,3-thiazolidin-4-ones

“…Antifungal properties of compounds containing sulfur and nitrogen have been well documented in literature [40,41,42,43,44,45,46]. Among these substances also various thiosemicarbazones [47,48,49,50,51,52] and derivatives of 1,3-thiazolidin-4-one were reported [53,54,55,56,57,58,59,60,61,62,63]. Compounds of this type were also studied by our research group and the results are discussed below.…”

Endothelial Dysfunction in Diabetes

“…Thiazolidinediones (TZDs) are antidiabetic agents that bind and activate peroxisome proliferator activated receptor γ (PPARγ), which is a nuclear receptor superfamily that improves insulin sensitivity. In addition, TZDs have attracted growing interest because of their biological activities, such as their anti-inflammatory, antitumor, and anti-atherosclerotic activities [ 99 ].…”

Crystal structures of two substituted thiazolidine derivatives

“…Among them, thiazolidines are the most extensively investigated class of compounds (Fun et al, 2011). Thiazolidine derivatives have attracted continuous interest over the years because of their varied biological activities (Shih et al, 2015). The special importance of the thiazolidine ring system derives from the fact that it plays an important role in medicinal chemistry.…”