Synthesis, crystal structure, Hirshfeld surface, biological evaluation, DFT and molecular docking studies of unsymmetrical 3-allyl-5-ethyl-1,4-dihydro-2,6-dimethyl-4-phenyl pyridine-3,5-dicarboxylate derivatives

• Published in: Molecular physics Vol. 121; no. 6
• Main Authors: Arulvani, K., Venkateswaramoorthi, R., Gunavathi, S., Bharanidharan, S.
• Format: Journal Article
• Language: English
• Published: Abingdon Taylor & Francis 19.03.2023; Taylor & Francis Ltd
• Subjects: Ammonium nitrate; Antiinfectives and antibacterials; Binding sites; Cerium ammonium nitrate; Charge transfer; Crystal structure; DFT; Hantzsch reaction; Hirshfeld; Hydrogen bonds; Mathematical analysis; Molecular docking; Molecular orbitals; Piperidine; Pyridine dicarboxylate; Receptors; Single crystals; Spectral methods; Stability analysis; Structural stability; Surface analysis (chemical); Unsymmetrical 1,4-dihydropyridines; X-ray diffraction
• ISSN: 0026-8976; 1362-3028
• DOI: 10.1080/00268976.2023.2200845

By employing ceric ammonium nitrate as an effective catalyst in the one-pot four-component Hantzsch reaction, a new series of unsymmetrical 1, 4-dihydropyridines were synthesised. The synthesised compounds were identified using spectral methods and the structure of the compound 3-allyl-5-ethyl-4(3-fluorophenyl)-1,4-dihydro-2,6-dimethyl-4-phenylpyridine-3,5-dicarboxylate (5f) was confirmed by single crystal XRD analysis. Optimised bond parameters were calculated using DFT /B3LYP/6-311++(d,p) basis set and also  compared with single crystal XRD data. The calculated hyperpolarisability may be attractive for further studies on the material's NLO properties. NBO analysis was used to examine the stability of the molecule resulting from the hyper conjugative interaction and charge delocalisation. The eventual charge transfer interactions that occur within the molecule are explained by HOMO-LUMO analysis. MEP reveals the electrophilic and nucleophilic reactive sites of the molecule. According to the Hirshfeld surface analysis, the intermolecular stabilisation in the crystal is mostly caused by hydrogen bond interactions between H ... H, C-H ... C, C-H ... N, and particularly C-H-O. It was discovered that the chemicals 5d and 5i were effective antimicrobials activity. Molecular docking studies were employed to identify the primary binding site of piperidine to receptors. These results indicate that the target molecules may be considered for further drug design endeavours. Research highlights Compound synthesised by the one-pot four component Hantzsch method. Single crystal of 3-allyl-5-ethyl-4(3-fluorophenyl)−1,4-dihydro-2,6-dimethyl-4-phenylpyridine-3,5-dicarboxylate(5f) was obtained by slow evaporation method. Hirshfeld analysis and fingerprint plots were performed to confirm the intermolecular interactions in the crystal structure. The stability and reactivities of 5f was achieved from DFT calculation. The antimicrobial studies showed that compounds have promising antimicrobial properties. Molecular docking studies were employed to identify the primary binding site of piperidine to receptors.