Integrated experimental and computational investigation of a novel carbazole-based dihydropyridine derivative: Synthesis, spectroscopic analysis, molecular docking, and dynamics studies

Diethyl 4-(4-(9H-carbazol-9-yl)phenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (DHPC) is a novel compound with potential pharmacological and biomedical applications. Its unique structural features and electronic properties make it a promising candidate for drug discovery and molecular interaction studies. This novel compound, DHPC was synthesized using the classical Hantzsch route. Comprehensive experimental and theoretical studies were conducted to investigate its structural, vibrational, NMR, and electronic properties. Density Functional Theory (DFT) calculations employing the B3LYP exchange-correlation functional were used to correlate molecular and structural characteristics. The electronic properties of DHPC, including the energy band gap between the HOMO-LUMO orbitals, were calculated using TD-DFT/B3LYP/6–311++G(d,p) basis set. Natural Bond Orbital (NBO) analysis was performed to evaluate the compound's strength and stability. The 1 H NMR and 13 C NMR spectra were investigated using the Gauge-Independent Atomic Orbital (GIAO) method, with tetramethylsilane (TMS) as a reference. Global reactivity parameters such as Fukui functions, and the molecular electrostatic potential (MEP) map were employed to identify reactive sites within the compound. These DFT-derived electronic and structural insights contribute to understanding the potential pharmacological actions of DHPC. Further, molecular docking analysis was performed to identify the binding interactions of the ligand with target proteins, revealing the possible binding sites. The stability and dynamics of the protein-ligand complex were assessed through molecular dynamics simulations. These integrated studies provide a robust framework for exploring DHPC's potential in pharmacological and biomedical applications.