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Insights into solvation, chemical reactivity, structural, vibrational and anti-hypertensive properties of a thiazolopyrimidine derivative by DFT and MD simulations

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Abstract

In this study, a thiazolopyrimidine derivative ethyl 2-(2-acetoxyphenyl)-5-(4 (benzyloxy) phenyl)-7-methyl-3-oxo-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6 carboxylate (EAPC) was investigated experimentally and theoretically. FMOs (frontier molecular orbitals), MEP, ALIE surfaces and solvation free energies were calculated for EAPC at CAM-B3LYP/6–311++G(2d,p) level. Solvation free energies in water, ethanol, acetone, acetonitrile, and chloroform were obtained and the analysis of the energy values suggests that acetone and acetronitrile may be better for solubilization of EAPC. However, the value of solvation energy in water (hydration free energy) indicates good solubility of the studied molecule in an aqueous medium, factor that corroborates the biological activity. Vibrational analysis, together with potential energy distribution (PED) calculations, revealed several characteristic vibrations. Molecular docking and molecular dynamics simulations carreid out with angiotensin I-converting enzyme revealed that EAPC is a promising antihypertensive candidate.

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All data generated or analyzed during this study are included in this published article.

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Acknowledgements

The authors express their gratitude to Princess Nourah bint Abdulrahman University Researchers Supporting Project of Princess Nourah bint Abdulrahman University, Riyadh, Saudi Arabia.

Funding

This work was financially supported by Princess Nourah bint Abdulrahman University Researchers Supporting Project (Grant number PNURSP2022R13).

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Authors and Affiliations

  1. Department of Chemistry, College of Science, Princess Nourah Bint Abdulrahman University, P.O. Box 84428, Riyadh, 11671, Saudi Arabia

    Jamelah S. Al-Otaibi

  2. Department of Chemistry, Federal University of Amazonas (DQ-UFAM), Manaus, AM, 69080-900, Brazil

    Renyer Alves Costa, Emmanoel Vilaça Costa & Victor Lima Tananta

  3. Thushara, Neethinagar-64, Kollam, Kerala, India

    Y. Sheena Mary & Y. Shyma Mary

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Contributions

All the authors contributed to the study conception and design. Synthesis of the compound, fund acquisition, data collection, docking calculations, and first writing were performed by Jamelah S.Al-Otaibi. DFT calculations, optimization of structures, review, and editing were performed by Renyer A. Costa, Victor L. Tananta, and Emmanoel V. Costa. Molecular docking, molecular dynamic calculations, spectroscopic analysis, writing, and supervision were performed by Y. Sheena Mary and Y. Shyma Mary. All the authors read and approved the final manuscript.

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Correspondence to Jamelah S. Al-Otaibi or Renyer Alves Costa.

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Al-Otaibi, J.S., Costa, R.A., Costa, E.V. et al. Insights into solvation, chemical reactivity, structural, vibrational and anti-hypertensive properties of a thiazolopyrimidine derivative by DFT and MD simulations. Struct Chem 33, 1271–1283 (2022). https://doi.org/10.1007/s11224-022-01931-1

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