A novel julolidine-based Schiff base: Crystal structure, DFT calculations, drug-likeness and molecular docking
Journal of Molecular Structure, vol.1368, 2026 (SCI-Expanded, Scopus)
- Publication Type: Article / Article
- Volume: 1368
- Publication Date: 2026
- Doi Number: 10.1016/j.molstruc.2026.146270
- Journal Name: Journal of Molecular Structure
- Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Chemical Abstracts Core, Chimica, Compendex, INSPEC, Academic Search Ultimate (EBSCO), Engineering Source (EBSCO)
- Keywords: DFT, Drug-likeness, Hirshfeld surface analysis, Julolidene, X-ray
- Ondokuz Mayıs University Affiliated: No
Abstract
In this study, a novel julolidine-derived Schiff base, 9-((((8-hydroxy-1,1,6,6-tetramethyl-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)methylene)hydrazono)methyl)-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-8-ol (HBTQ),was synthesized and reported for the first time. Single-crystal X-ray diffraction analysis revealed that the compound crystallizes in the centrosymmetric space group, with the asymmetric unit comprising half of the molecule. The structural characterization of the synthesized compound was further supported by FT-IR and UV-Vis spectroscopic techniques. Geometric parameters, such as bond lengths and angles, were determined through detailed structural analysis, which also facilitated the evaluation of intramolecular interactions. Theoretical investigations—encompassing geometry optimization, total energy, dipole moment, atomic charges, and molecular electrostatic potential (MEP) mapping—were conducted. Additionally, spectroscopic parameters (IR, UV-Vis) along with electronic and thermodynamic properties were calculated using the Gaussian 09 software package. The experimental findings demonstrated a high degree of correlation with the quantum mechanical data. Furthermore, Hirshfeld surface analysis was employed to quantify intermolecular interactions, and a drug-likeness study was performed to evaluate the pharmacological potential of the synthesized molecule. Finally, molecular docking simulations were performed to elucidate the binding mode of the compound within the target protein's active site.