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Molecular docking, expounding the regiospecificity, stereoselectivity, and the mechanism of [5+2] cycloaddition reaction between ethereal ether and oxidopyrylium

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Abstract

Application of molecular electron density theory (MEDT) to investigate the [5+2] cycloaddition reaction between oxidopyrylium and ethervinylether, we discovered that oxidopyrylium is an electrophile and ethervinylether is a nucleophile by an examination of conceptual DFT indices. Analysis of energetical parameters shows clearly that this cycloaddition is both regio- and stereoselective, which is extremely consistent with the experience. Topological analysis of the electron localization function (ELF) has shown that this [5+2] cycloaddition is achieved by a two-step, single-step mechanism along the most favored route. Aside from that, docking outcomes show that the (1–20) oxabicyclo[3.2.1]octene derivatives have a significant anti-HIV potential.

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Acknowledgements

The authors extend their appreciation to the Researchers Supporting Project (number RSP2023R15), King Saud University, Riyadh, Saudi Arabia and we would like to thank Ling Shing Wong for supporting this research.

Funding

The authors extend their appreciation to the Researchers Supporting Project (number RSP2023R15), King Saud University, Riyadh, Saudi Arabia.

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Authors and Affiliations

  1. Molecular Modelling and Spectroscopy Research Team, Faculty of Science, Chouaïb Doukkali University, P.O. Box 20, 24000, El Jadida, Morocco

    Anas Ouled Aitouna & Abdellah Zeroual

  2. Laboratory of Bioorganic Chemistry, Department of Chemistry Faculty of Sciences, Chouaïb Doukkali University, P. O. Box 20, 24000, El Jadida, Morocco

    Anas Ouled Aitouna & Noureddine Mazoir

  3. Department of Botany and Microbiology, College of Science, King Saud University, P.O. Box 2455, 11451, Riyadh, Saudi Arabia

    Asad Syed, Ali H. Bahkali & Abdallah M. Elgorban

  4. University Centre for Research & Development, Department of Chemistry, Chandigarh University Gharuan, Mohali, India

    Meenakshi Verma

  5. Team of Chemical Processes and Applied Materials, Faculty Polydisciplinary, Sultan Moulay Slimane University, Beni-Mellal, Morocco

    Mohammed El idrissi

  6. Department of Organic Chemistry and Technology, Cracow University of Technology, Warszawska 24, 31‐155, Cracow, Poland

    Radomir Jasiński

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  1. Anas Ouled Aitouna
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Contributions

Anas Ouled Aitouna, Abdellah Zeroual: article writing. Abdellah Zeroual and Noureddine Mazoir: numerical calculations; Abdallah M. Elgorban, Ali H. Bahkali, and Asad Syed: acquisition of data; Meenakshi Verma, Radomir Jasiński, and Mohammed El idrissi: final review and editing. All authors: analysis and interpretation of data and drafting the article.

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Correspondence to Mohammed El idrissi.

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Aitouna, A.O., Mazoir, N., Zeroual, A. et al. Molecular docking, expounding the regiospecificity, stereoselectivity, and the mechanism of [5+2] cycloaddition reaction between ethereal ether and oxidopyrylium. Struct Chem 35, 841–852 (2024). https://doi.org/10.1007/s11224-023-02239-4

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