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Synthesis, spectroscopic, DFT, and molecular docking studies on 1,4-dihydropyridine derivative compounds: a combined experimental and theoretical study

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Abstract

Dihydropyridines are the most extensively used drugs in the treatment of hypertension. Nifedipine is the prototype of calcium channel blocker. The dihydropyridine derivative compounds of diethyl 4-(4-bromophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (DHPB), diethyl 4-(furan-2yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (DHPF), and diethyl-4-phenyl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (DHPP) were synthesized using the Hantzsch reaction. The DFT/B3LYP exchange–correlation function was employed to perform quantum chemical calculations such as molecular geometry optimization, vibrational analysis, frontier molecular orbital (FMO), molecular electrostatic potential (MEP), natural bond order (NBO), global reactive descriptors, and Fukui functions to determine the structural characteristics related to biological activity of the compounds. The molecular docking and molecular dynamics were employed to study the binding interaction and stability of protein–ligand complex in the docked site.

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Data availability

The data used in this study are available from the corresponding author upon interest.

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Acknowledgements

The authors gratefully acknowledge the Anna University, Chennai, and IIT Madras for providing facilities FT-IR, FT-Raman, and UV-Vis spectrometer to record the spectra of the samples.

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Authors and Affiliations

  1. Department of Physics, CEG Campus, Anna University, Chennai, 600025, Tamil Nadu, India

    R. Karthick & G. Velraj

  2. Department of Chemistry, Bannari Amman Institute of Technology, Sathyamangalam, 638401, Tamil Nadu, India

    M. P. Pachamuthu

  3. Department of Molecular Cell Biology, Sungkyunkwan University School of Medicine, Samsung Medical Center, Suwon, Republic of Korea

    S. Karthikeyan

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  1. R. Karthick
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Contributions

R. Karthick and S. Karthikeyan have performed simulation studies, and M. P. Pachamuthu has carried out synthesis of compounds. All these work are done under the guidance of Dr. G. Velraj.

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Correspondence to G. Velraj.

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Karthick, R., Velraj, G., Pachamuthu, M.P. et al. Synthesis, spectroscopic, DFT, and molecular docking studies on 1,4-dihydropyridine derivative compounds: a combined experimental and theoretical study. J Mol Model 28, 5 (2022). https://doi.org/10.1007/s00894-021-04939-2

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  • DOI: https://doi.org/10.1007/s00894-021-04939-2

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