Synthesis, anticonvulsant, antioxidant and binding interaction of novel N-substituted methylquinazoline-2,4(1H, 3H)-dione derivatives to bovine serum albumin: A structure–activity relationship study

• A new compounds NMQ was synthesized and characterized by 1H NMR, IR, and mass spectra.
• Anticonvulsant and antioxidant activity were performed for the prepared compounds.
• We explored the interaction of BSA and NMQ by spectroscopic methods.
• The binding constants, binding sites and binding distance were calculated.
• We have studied the structure–activity relationship to the synthesized compounds.

A novel class of N-substituted glycosmicine derivatives was synthesized, and their anticonvulsant, antioxidant activity and interaction with bovine serum albumin (BSA) were evaluated. The synthesized compounds 4a–j were examined for anticonvulsant activity by maximal electroshock induced seizures (MESs) test and their neurotoxic effects were determined by rotorod test in mice. The structure–activity relationships (SARs) of these compounds were also investigated. Compounds 4d, 4g, 4i and 4j were found to have good protective effect from seizure. The in vitro antioxidant activity was evaluated by 2,2-diphenyl-1-picrylhydrazyl (DPPH) and superoxide radical scavenging assay. The interaction between novel N-substituted methylquinazoline-2,4(1H, 3H)-dione (NMQ) and BSA was analyzed by fluorescence and ultraviolet spectroscopy at 304 K under simulative physiological conditions. BSA fluorescence quenched by NMQ is discussed according to the Stern–Volmer equation. The binding constant and binding sites of NMQ with BSA were calculated. According to Forster non-radiation energy transfer theory, the binding distance (r) between NMQ and BSA was calculated.

Novel anticonvulsant agents containing essential pharmocophoric elements in their structure.Figure optionsDownload as PowerPoint slide