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

Abstract

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.

3-Amino-5-(indol-3-yl)methylene-4-oxo-2-thioxothiazolidine Derivatives as Antimicrobial Agents: Synthesis, Computational and Biological Evaluation

“…Again, the formation of the hydrogen bond between the C=O group and Ser228 was observed. Thus, the obtained results support previous data [ 69 , 70 , 71 , 72 ] that MurB maybe is the most appropriate target for the antibacterial activity for this chemical series.…”

“…It was found that benzothiazole derivatives are mentioned as Gyrase inhibitors [ 66 , 67 , 68 ]. On the other hand, according to the literature, thiazolidinones act as MurB inhibitors [ 69 , 70 , 71 , 72 ]. Furthermore, prediction of the mechanism of action by computer program PASS indicated Thymidylate kinase as the probable antibacterial target.…”

“…In the case of our previous work [ 19 ], the most active compound interacts with the heme but throughout its benzene ring and the –NO 2 group, forming pi and negative ionizable interactions with the heme group, respectively. In the case of 5-adamantane thiadiazole-based thiazolidinones [ 72 ] , again, the most active compound form positive interactions between the heme group and heterocyclic rings of the compound. Thus, it can be concluded that thiazolidinone derivatives, in general, can interact with the heme of CYP51 Ca in the same way as ketoconazole interacts.…”