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Comprehensive study on the stereoselective epoxidation of aromatic atlantone: mechanism, ADME analysis, and potential as COVID-19 drug

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Chemistry of Heterocyclic Compounds Aims and scope

This work presents a theoretical investigation of the epoxidation reaction of 2-methyl-6-(4-methylphenyl)hept-2-en-4-one using hydrogen peroxide in the presence of sodium hydroxide and ethanol as a solvent. The study was conducted using density functional theory (DFT) with the 6-311G(d,p) basis set. Calculations of activation energies for the transition states revealed the stereoselectivity of the reaction, with theoretical results closely matching experimental data. Additionally, an electronic localization function (ELF) analysis was performed to clarify the reaction mechanism. A docking study was also conducted to predict potential drug candidates against COVID-19.

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References

  1. Lassaba, C. R.; ElJamili, H.; Chekroun, A.; Benharref, A.; Chiaroni, A.; Riche, C.; Lavergne, J.-P. Synth. Commun. 1998, 28(14), 2641.

    Article  CAS  Google Scholar 

  2. Bennouna, F.; Lachkar, M.; El Abed, S.; Koraichi, S. I. Moroccan J. Biol. 2019, 16, 35.

    Google Scholar 

  3. Kumar, A.; Singh, V.; Chaudhary, A. K. J. Ethnopharmacol. 2011, 134(2), 294.

    Article  PubMed  Google Scholar 

  4. El Had, M. A.; Oukhrib, A.; Zaki, M.; Urritogity, M.; Benharref, A.; Chauvin, R. Chin. Chem. Lett. 2020, 31, 1851.

    Google Scholar 

  5. Elhad, M. A.; Benharref, A.; El Ammari, L.; Saadi, M.; Mazoir, N.; Berraho, M. IUCrData 2018, 3, 180083. https://doi.org/10.1107/S2414314618000834 II.

    Article  Google Scholar 

  6. Uehara, A.; Tommis, B.; Belhassen, E.; Satrani, B.; Ghanmi, M.; Baldovini, N. Phytochemistry 2017, 144, 208.

    Article  CAS  PubMed  Google Scholar 

  7. Jaouadi, I.; Cherrad, S.; Bouyahya, A.; Koursaoui, L.; Satrnai, B.; Ghanmi, M.; Chaouch, A. Arabian J. Chem. 2021, 14(12), 103441.

    Article  CAS  Google Scholar 

  8. Aitouna, A. O.; Lahoucine, B.; El Ayouchia, H. B.; Benharref, A. Mediterr. J. Chem. 2019, 9(2), 133.

    Article  CAS  Google Scholar 

  9. Belkacem, N.; Khettal, B.; Hudaib, M.; Bustanji, Y.; Abu-Irmaileh, B.; Amrine, C. S. M. Eur. J. Integr. Med. 2021, 42, 101292.

    Article  Google Scholar 

  10. Martins, D. F.; Emer, A. A.; Batisti, A. P.; Donatello, N.; Carlesso, M. G.; Mazzardo-Martins, L.; Venzke, D.; Micke, G. A.; Pizzolatti, M. G.; Piovezan, A. P.; dos Santos, A. R. S. J. Ethnopharmacol. 2015, 175, 30.

    Article  CAS  PubMed  Google Scholar 

  11. Boutekedjiret, C.; Hellal, A.; Fabiano-Tixier, A.-S.; Abert-Vian, M.; Chemat, F. Green Food Process. Tech. 2019, 369. https://doi.org/10.1016/B978-0-12-815353-6.00013-6.

  12. Buchi, G.; Fowler, K. W.; Nadzan, A. M. J. Am. Chem. Soc. 1982, 104, 544.

    Article  Google Scholar 

  13. Satrani, B.; Aberchane, M.; Farah, A.; Chaouch, A.; Talbi, M. Acta Bot. Gallica 2006, 153(1), 97.

    Article  CAS  Google Scholar 

  14. Apparu, M.; Barrelle, M. Tetrahedron 1978, 34(11), 1691.

    Article  CAS  Google Scholar 

  15. Angeles, G. H.; Contreras-Ordoñez, G.; Alvarez, C.; Santes, V.; Gómez, E.; Toscano, R. A. Synth. Commun. 2004, 34(13), 2393.

    Article  Google Scholar 

  16. El Haib, A.; Benharref, A.; Parres-Maynadie, S.; Manoury, E.; Daran, J.-C.; Urrutigoïty, M.; Gouygou, M. Tetrahedron: Asymmetry 2010, 21(9–10), 1272.

    Article  Google Scholar 

  17. Xiao, H.-Q.; Shu, X.-Z.; Ji, K.-G.; Qi, C.-Z.; Liang, Y.-M. Catal. Commun. 2009, 10(14), 1824.

    Article  CAS  Google Scholar 

  18. Layachi, K.; Ariès-Gautron, I.; Guerro, M.; Robert, A. Tetrahedron 1992, 48(9), 1585.

    Article  CAS  Google Scholar 

  19. Adolph, M.; Zevaco, T. A.; Altesleben, C.; Walter, O.; Dinjus, E. Dalton Trans. 2014, 43(8), 3285.

    Article  CAS  PubMed  Google Scholar 

  20. Zahedi, S.; Safaei, E. J. CO2 Util. 2020, 42, 101308.

  21. Aresta, M.; Nocito, F.; Dibenedetto, A. Adv. Catal. 2018, 62, 49.

    Article  CAS  Google Scholar 

  22. Allonas, X.; Lecompère, M.; Gachet, B.; Criqui, A.; Maréchal, D.; Croutxé-Barghorn, C. Polym. Chem. 2021, 12(47), 6846.

    Article  CAS  Google Scholar 

  23. Kwong, H.-K.; Lo, P.-K.; Lau, K.-C.; Lau, T.-C. Chem. Commun. 2011, 47, 4273.

    Article  CAS  Google Scholar 

  24. Kaur, B.; Singh, P. Bioorg. Chem. 2022, 125, 105862.

    Article  CAS  PubMed  Google Scholar 

  25. Marco-Contelles, J.; Molina, M. T.; Anjum, S. Chem. Rev. 2004, 104(6), 2857.

    Article  CAS  PubMed  Google Scholar 

  26. Gomes, A. R.; Varela, C. L.; Tavares-da-Silva, E. J.; Roleira, F. M. F. Eur. J. Med. Chem. 2020, 201, 112327.

    Article  CAS  PubMed  Google Scholar 

  27. Eljamili, A.; Auhmani, A.; Dakir, M.; Lassaba, E.; Benharref, A.; Pierrot, M.; Chiaroni, A.; Riche, C. Tatrahedron Lett. 2002, 43, 6645.

    Article  CAS  Google Scholar 

  28. Lassaba, E.; Chekroun, A.; Benharref, A.; Chiaroni, A.; Riche, C.; Lavergne, J.-P. Bull. Soc. Chim. Belg. 1997, 106(5), 281.

    CAS  Google Scholar 

  29. Chiaroni, A.; Riche, C.; Benharref, A.; El Jamili, H.; Lassaba, E. Acta Crystallogr., Sect. C: Struct. Chem. 1995, C51, 1171.

  30. El Idrissi, K.; Abdoul-Hakim, M.; Saleh, N.; Garmes, H.; Syed, A.; Ríos-Gutiérrez, M.; Paray, B. A.; Verma, M.; Zeroual, A.; Domingo, L. R. Sci. Rep. 2024, 14, 16827.

    Article  PubMed  PubMed Central  Google Scholar 

  31. Desjardins, M.-A. Ph. D. Thesis; Montreal, 2008. https://archipel.uqam.ca/1047/1/M10355.pdf.

  32. Barhoumi, A.; Ryachi, K.; Belghiti, M. E.; Chafi, M.; Tounsi, A.; Syed, A.; El Idrissi, M.; Wong, L. S.; Zeroual, A. J. Fluoresc. 2024, 34, 1913.

    Google Scholar 

  33. Kohanoff, J.; Gidopoulos, N. I. In Handbook of Molecular Physics and Quantum Chemistry; Wilson, S.; Bernath, P. F.; McWeeny, R., Eds.; Wiley-Blackwell, 2003, Vol. 2, part 5, p. 532.

  34. Ryachi, K.; El Idrissi, M.; Mohammad-Salim, H.; Bahkali, A. H.; de Julián-Ortiz, J. V.; Zeroual, A.; Wang, S.; Wong, L. S.; Syed, A.; Tounsi, A. Monatsh. Chem. 2024, 155, 697.

    Article  CAS  Google Scholar 

  35. Atif, M.; Barhoumi, A.; Syed, A.; Bahkali, A. H.; Chafi, M.; Tounsi, A.; Zeroual, A.; Paray, B. A.; Wang, S.; El Idrissi, M. Mol. Biotechnol. 2024. https://doi.org/10.1007/s12033-024-01105-w.

    Article  PubMed  Google Scholar 

  36. Samir, B. Ph. D. Thesis; Annaba, 2013. https://biblio.univannaba.dz/wp-content/uploads/2014/07/final.pdf

  37. Riffet, V. Ph. D. Thesis; Paris, 2014. https://pastel.hal.science/tel-01084858v1/document.

  38. Amaouch, M. Ph. D. Thesis; Paris, 2016. https://theses.hal.science/tel-01535533/.

  39. Pandey, K. A.; Mishra, V. N.; Singh, V. Iran. J. Chem. Chem. Eng. 2020, 39(1), 233.

    Google Scholar 

  40. Domingo, L. R.; Pérez, P. Org. Biomol. Chem. 2011, 9(20), 7168.

    Article  CAS  PubMed  Google Scholar 

  41. Domingo, L. R.; Aurell, M. J.; Pérez, P.; Contreras, R. Tetrahedron 2002, 58(22), 4417.

    Article  CAS  Google Scholar 

  42. Parr, R. G.; Szentpály, L. V.; Liu, S. J. Am. Chem. Soc. 1999, 121(9), 1922.

    Article  CAS  Google Scholar 

  43. El Idrissi, K. E.; Abdoul-Hakim, M.; Saleh, N.; Garmes, H.; Syed, A.; Ríos-Guttiérez, M.; Paray, B. A.; Verma, M.; Zeroual, A.; Domingo, L. R. Sci. Rep. 2024, 14, 16827.

    Article  PubMed  PubMed Central  Google Scholar 

  44. Juanes, M.; Saragi, R. T.; Caminati, W.; Lesarri, A. Chem.– Eur. J. 2019, 25, 11402.

  45. Berski, S.; Andrés, J.; Silvi, B.; Domingo, L. R. J. Phys. Chem. A 2006, 110(51), 13939.

    Article  CAS  PubMed  Google Scholar 

Download references

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Authors and Affiliations

  1. Natural Substances Chemistry Laboratory, Semlalia Faculty of Sciences, Cadi Ayyad University, Marrakech, Morocco

    Houria Raji, Ahmed Chekroun & Ahmed Benharref

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

    Houria Raji & Abdellah Zeroual

  3. Molecular Topology and Drug Design Research Unit, Department of Physical Chemistry, Pharmacy Faculty, University of Valencia, Burjassot, 46100, Valencia, Spain

    Haydar Mohammad-Salim & Jesús Vicente de Julián-Ortiz

  4. Department of Chemistry, Faculty of Science, University of Zakho, Zakho, 42002, Duhok, Kurdistan Region, Iraq

    Haydar Mohammad-Salim

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

    Asad Syed

  6. Centre of Excellence in Biotechnology Research (CEBR), King Saud University, Riyadh, Saudi Arabia

    Abdallah M. Elgorban & Islem Abid

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

    Meenakshi Verma

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  1. Houria Raji
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Correspondence to Abdellah Zeroual.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2024, 60(11/12), 568–574

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Raji, H., Zeroual, A., Chekroun, A. et al. Comprehensive study on the stereoselective epoxidation of aromatic atlantone: mechanism, ADME analysis, and potential as COVID-19 drug. Chem Heterocycl Comp 60, 568–574 (2024). https://doi.org/10.1007/s10593-025-03379-7

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