New 5-iodoisatin-thiosemicarbazones: preparation, spectroscopic characterization, antioxidant, urease inhibition activities, DFT studies, molecular docking, and molecular dynamic simulations
摘要
New isatin-thiosemicarbazone compounds (1–7) were synthesized from numerous thiosemicarbazides and 5-iodoisatin with high yields and efficient methods. The compounds' structures were characterized through FT-IR, 1H NMR, and 13C NMR spectroscopy, supported by elemental analysis. Density functional theory (DFT) calculations were employed to investigate the structural and electronic properties of the compounds, with a discussion on their correlation to antioxidant activity. The antioxidant potential of the synthesized compounds was evaluated in vitro using the 1,1-diphenyl-2-picryl hydrazyl (DPPH.) free radical scavenging assay. These compounds exhibited IC50 values ranging from 15.36 ± 0.03 to 22.46 ± 0.05 μM, with compound 7 demonstrating the best antioxidant activity among them. The free radical scavenging effects of the compounds, based on their IC50 values, followed the order: 7 > 4 > 6 > 5 > 3 > 2 > 1. Urease inhibition of the samples and their interactions with urease were examined, and it was determined that compound 2 showed the best inhibition effect and interaction as 1.62 ± 0.05 µg/mL and − 7.70 kcal/mol, respectively. Molecular docking was used to ascertain how each molecule interacted with the active areas of the urease enzymes. In addition, molecular dynamics simulation was performed to determine the state of the complex it formed with the enzyme. The current study determined that in vivo biochemical tests of effective thiosemicarbazones could be used to evaluate useful application sectors such as the biological and pharmaceutical fields.
Graphical abstractNew thiosemicarbazone derivatives containing 5-iodoisatin have been synthesized, and their structures have been characterized using various spectroscopic techniques. The antioxidant activity of these compounds was assessed using the DPPH. assay. Additionally, the urease inhibitory effects of the compounds were evaluated, and their interactions with the urease enzyme were studied. Molecular docking studies were conducted to explore how each compound interacts with the active sites of the urease enzyme. Furthermore, molecular dynamics simulations were carried out to investigate the stability and conformation of the enzyme inhibitor complex.