Akademik Veri Yönetim Sistemi
JOURNAL OF MOLECULAR STRUCTURE, 2024 (SCI-Expanded)
In this study, three new N-acylhydrazone derivatives with the structural motif of N'-(substitutedbenzylidene)-3(5-methyl-2-benzoxazolinon-3-yl)propanehydrazide (5a 5a-c ) are prepared and evaluated for their MAO inhibitory activities. The structures of the synthesized compounds are elucidated through spectral methods (IR,( 1) H-NMR,( 13) C-NMR), elemental analysis and single crystal X-ray crystallography. Detailed structural and Hirshfeld surface analyses of compounds (5a 5a-c ) have provided further insights into their molecular and crystal structures and also their intermolecular interactions. Complementing the spectral and structural analyses confirmed the E-configurations of the compounds in the solid state. The Hirshfeld surface analyses of the crystal structures have indicated that the most important contributions for the crystal packings are from H ... H, H ... C/C ... H and H ... O/O ... H (for 5a-c ) and H ... F/F ... H (for 5b and c ). In vitro tests are revealed their MAO inhibitory activities, surpassing reference compounds moclobemide and selegiline. Notably, synthesized N-acylhydrazone derivatives (5a 5a-c ) are exhibited superior MAO inhibitory activities, with a higher selectivity for MAOB over MAOA (SI >10). Molecular docking studies are provided insights into the binding modes of the compounds in the active site of the target enzyme. Theoretical ADME (Absorption, Distribution, Metabolism and Excretion), gastrointestinal absorption and blood-brain barrier permeation studies revealed that the compounds possess pharmacological attributes resembling those of typical drugs. This properties and MAO inhibitory activities of N-acyl hydrazone derivatives emphasize their potentials as promising candidates in the field of medicinal chemistry.