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. 2015 Apr 13;20(4):6520-32.
doi: 10.3390/molecules20046520.

A facile synthesis and antimicrobial activity evaluation of sydnonyl-substituted thiazolidine derivatives

Mei-Hsiu Shih  1 , Yu-Yuan Xu  2 , Yu-Sheng Yang  3 , Guan-Ling Lin  4
Affiliations

A facile synthesis and antimicrobial activity evaluation of sydnonyl-substituted thiazolidine derivatives

Mei-Hsiu Shih et al. Molecules. .

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.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Synthesis of thiazolidinone derivatives 4a–d, 5a–d from sydnone compounds 1a–d. a: Ar = C6H5; b: Ar = p-CH3C6H4; c: Ar = p-CH3OC6H4; d: Ar = p-C2H5OC6H4.
Figure 1
Figure 1
ORTEP drawing of 5-[3-(4-methylphenyl)sydnon-4-ylmethylene]thiazolidine-2,4-dione (4b).
Figure 2
Figure 2
ORTEP drawing of 5-(3-phenylsydnon-4-ylmethylene)-2-thioxothiazolidin-4-one (5a).
Figure 3
Figure 3
View along the b axis of packing diagram of compound 5a.
Figure 4
Figure 4
(a) The relative inhibition activity of compounds 4a–d and 5a–d against Aspergillus niger; (b) The relative inhibition activity of compounds 4a–d and 5a–d against Penicillium citrinum. G: Griseofulvin.
See this image and copyright information in PMC

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