Synthesis of eugenol derivative by the ring opening of epoxide eugenol and its analysis through chemical reactivity: a DFT approach

References

• Abdou A, Elmakssoudi A, El Amrani A, JamalEddine J, Dakir M. 2021. Recent advances in chemical reactivity and biological activities of eugenol derivatives. Med Chem Res. 30(5):1011–1030.
   Web of Science ®Google Scholar
• Abdou A, Idouaarame S, Salah M, Nor N, Zahm S, ElMaksoudi A, Mazoir N, Benharref A, Dari A, JamalEddine J, et al. 2022. Phytochemical study: molecular docking of eugenol derivatives as antioxidant and antimicrobial agents. Lett Org Chem. 19:1–10.
   Web of Science ®Google Scholar
• Abrão PHO, Pizi RB, De Souza TB, Silva NC, Fregnan AM, Silva FN, Coelho LFL, Malaquias LCC, Dias ALT, Dias DF, et al. 2015. Synthesis and biological evaluation of new eugenol mannich bases as promising antifungal agents. Chem Biol Drug Des. 86(4):459–465.
   PubMed Web of Science ®Google Scholar
• Akbar L, Juliandi B, Boediono A, Batubara I, Subangkit M. 2021. Effects of eugenol on memory performance, neurogenesis, and dendritic complexity of neurons in mice analyzed by behavioral tests and golgi staining of brain tissue. J Stem Cells Regen Med. 17(1):35–41.
   PubMed Web of Science ®Google Scholar
• Al Zoubi W, Putri RAK, Ko YG. 2021. Understanding the metal ion-ligand responsible in the plasma-assisted electrochemical reactions for optimizing chemical stability. J Mol Liq. 321(1):1–7.
   Google Scholar
• Becke AD. 1988. Density-functional exchange-energy approximation with correct asymptotic behavior. Phys Rev A Gen Phys. 38(6):3098–3100.
   PubMedGoogle Scholar
• Belaidi S, Melkemi N, Bouzidi D. 2012. Molecular geometry and structure-property relationships for 1,2-dithione-3-thione derivatives. Int J Chem Res. 4(2):134–139.
   Google Scholar
• Chakraborty D, Chattaraj PK. 2021. Conceptual density functional theory based electronic structure principles. Chem Sci. 12(18):6264–6279.
   PubMed Web of Science ®Google Scholar
• Cohen AJ, Mori-s P, Yang W. 2012. Challenges for density functional theory. Chem Rev. 112(1):289–320.
   PubMed Web of Science ®Google Scholar
• Das Chagas Pereira de Andrade F, Mendes AN. 2020. Computational analysis of eugenol inhibitory activity in lipoxygenase and cyclooxygenase pathways. Sci Rep. 10(1):1–14.
   PubMed Web of Science ®Google Scholar
• Deshpande N, Parulkar A, Joshi R, Diep B, Kulkarni A, Brunelli NA. 2019. Epoxide ring opening with alcohols using heterogeneous Lewis acid catalysts: Regioselectivity and mechanism. J Catal. 370(2):46–54.
   Google Scholar
• De Souza TB, Orlandi M, Coelho LFL, Malaquias LCC, Dias ALT, De Carvalho RR, Silva NC, Carvalho DT. 2014. Synthesis and in vitro evaluation of antifungal and cytotoxic activities of eugenol glycosides. Med Chem Res. 23(1):496–502.
   Web of Science ®Google Scholar
• Domingo LR, Patricia P. 2011. The nucleophilicity N index in organic chemistry. Org Biomol Chem. 9(20):7168–7175.
   PubMed Web of Science ®Google Scholar
• Dos Santos T, Coelho C, Elias T, Siqueira F, Nora E, de Campos M, de Souza G, Coelho L, Carvalho D. 2019. Synthesis and biological evaluation of new eugenol-derived 1,2,3-triazoles as antimycobacterial agents. J Braz Chem Soc. 30(7):1425–1436.
   Web of Science ®Google Scholar
• Elshakre ME, Noamaan MA, Moustafa H, Butt H. 2020. Density functional theory, chemical reactivity, pharmacological potential and molecular docking of dihydrothiouracil-indenopyridopyrimidines with human-DNA topoisomerase II. IJMS. 21(4):1253–1227. (
   Google Scholar
• Eyambe G, Canales L, Banik BK. 2011. Antimicrobial activity of eugenol derivatives. Heterocycl Lett. 1(2):2231–3087.
   Google Scholar
• Gázquez JL. 2008. Perspectives on the density functional theory of chemical reactivity. J Mex Chem Soc. 52(1):3–10.
   Web of Science ®Google Scholar
• Geerlings P, Chamorro E, Kumar PC, Frank DP, José LG, Shubin L, Christophe M, Alejandro T, Alberto V, Pau A. 2020. Conceptual density functional theory: status, prospects, issues. Theor Chem Acc. 139(2):1–18.
   Web of Science ®Google Scholar
• Hamri BS, Rhazri K, Hafid A, Ouchetto H, Hajbi Y, Khouili M. 2013. Clove (Eugenia Caryophyllata) extraction and synthesis of new pyrazole derivatives from eugenol. Glob J Sci Front Res Chem. 13(7):1–6.
   Google Scholar
• Irie Y. 2006. Effects of eugenol on the central nervous system: its possible application to treatment of Alzheimers disease, depression, and Parkinsons disease. CBC. 2(1):57–66.
   Google Scholar
• Kaufman TS. 2015. The multiple faces of Eugenol. A versatile starting material and building block for organic and bio-organic synthesis and a convenient precursor toward bio-based fine chemicals. J Braz Chem Soc. 26(6):1055–1085.
   Web of Science ®Google Scholar
• Khalil AA, Rahman UUR, Khan MR, Sahar A, Mehmood T, Khan M. 2017. Essential oil eugenol: sources, extraction techniques and nutraceutical perspectives. RSC Adv. 7(52):32669–32681.
   Web of Science ®Google Scholar
• Kit-Kay M, Kamal MB, Sunday BA, Raghavendra S, Kang YB, Kavitha M, Madhu KB, Sazali HA, Mallikarjuna RP. 2019. A comprehensive review on Eugenol’s antimicrobial properties and industry applications: a transformation from ethnomedicine to industry. Phcog Rev. 13(25):1–9.
   Google Scholar
• Lane T, Anantpadma M, Freundlich JS, Davey RA, Madrid PB, Ekins S. 2019. The natural product eugenol is an inhibitor of the Ebola virus in vitro. Pharm Res. 36(7):2–7.
   Web of Science ®Google Scholar
• Lee C, Yang W, Parr RG. 1988. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B Condens Matter. 37(2):785–789.
   PubMed Web of Science ®Google Scholar
• Machado M, Dinis AM, Salgueiro L, Custódio JBA, Cavaleiro C, Sousa MC. 2011. Anti-Giardia activity of Syzygium aromaticum essential oil and eugenol: Effects on growth, viability, adherence and ultrastructure. Exp Parasitol. 127(4):732–739.
   PubMed Web of Science ®Google Scholar
• Marchese A, Barbieri R, Coppo E, Orhan IE, Daglia M, Nabavi SF, Izadi M, Abdollahi M, Nabavi SM, Ajami M. 2017. Antimicrobial activity of eugenol and essential oils containing eugenol: a mechanistic viewpoint. Crit Rev Microbiol. 43(6):668–689.
   PubMed Web of Science ®Google Scholar
• Marco FP, Gázquez JL. 2019. Electronegativities of Pauling and Mulliken in density functional theory. J Phys Chem. 123(10):10065–10071.
   Google Scholar
• Marenich AV, Cramer CJ, Truhlar DG. 2009. Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions. J Phys Chem B. 113(18):6378–6396.
   PubMed Web of Science ®Google Scholar
• Martell JM, Goddard JD, Eriksson LA. 1997. Assessment of basis set and functional dependencies in density functional theory: studies of atomization and reaction energies. J Phys Chem A. 101(10):1927–1934.
   Web of Science ®Google Scholar
• Maurya AK, Agarwal K, Gupta AC, Saxena A, Nooreen Z, Tandon S, Ahmad A, Bawankule DU. 2018. Synthesis of eugenol derivatives and its anti-inflammatory activity against skin inflammation. Nat Prod Res. 34(2):1–10.
   Web of Science ®Google Scholar
• Maynard AT, Huang M, Rice WG, Covell DG. 1998. Reactivity of the HIV-1 nucleocapsid protein p7 zinc finger domains from the perspective of density-functional theory. Proc Natl Acad Sci USA. 95(20):11578–11583.
   PubMed Web of Science ®Google Scholar
• Nour H, Abdou A, Belaidi S, Jamal J, Elmakssoudi A, Dakir M, Chtita S. 2022. Discovery of promising cholinesterase inhibitors for Alzheimer’s disease treatment through DFT, docking, and molecular dynamics studies of eugenol derivatives. J Chinese Chem Soc. 69(9):1534–1551.
   PubMed Web of Science ®Google Scholar
• Ouattara L, Bamba K, Kone MG, Stéphane N, Bede LA, N’guessan NK, Soro D. 2021. Theoretical studies of the chemical reactivity of a series of Coumarin derivatives by the density functional theory. Am Sci Res J Eng Technol Sci. 75(1):17–28.
   Google Scholar
• Parr RG, Szentpaly L v, Liu S. 1999. Electrophilicity index. J Am Chem Soc. 121(9):1922–1924.
   Web of Science ®Google Scholar
• Pearson RG. 2005. Chemical hardness and density functional theory. J Surf Sci Technol. 117(5):369–377.
   Google Scholar
• Pinto E, Vale-Silva L, Cavaleiro C, Salgueiro L. 2009. Antifungal activity of the clove essential oil from Syzygium aromaticum on Candida Aspergillus and dermatophyte species. J Med Microbiol. 58(Pt 11):1454–1462.
   PubMed Web of Science ®Google Scholar
• Rahim EA, Sanda F. 2019. Synthesis and functionality of eugenol-based polyacetylenes. J Phys Conf Ser. 1242(1):1–4.
   Google Scholar
• Ulanowska M, Olas B. 2021. Biological properties and prospects for the application of eugenol—a review. Int J Mol Sci. 22(7):1–13.
   Web of Science ®Google Scholar
• Xu H, Xu DC, Wang Y. 2017. Natural indices for the chemical hardness/softness of metal cations and ligands. ACS Omega. 2(10):7185–7193.
   PubMed Web of Science ®Google Scholar
• Yadav RN, K Banik B. 2018. Studies on natural products: a facile epoxidation of eugenol. Mod Chem Appl. 06(02):254–255.
   Google Scholar
• Zeroual A, Hajbi AE. 2015. Understanding the regioselective and molecular mechanism of the TCE in cycloaddtion reaction (TCE + Cp) and addition reaction (TCE + HCl) using DFT calculation. Can Chem Trans. 3(4):430–437.
   Google Scholar
• Zeroual A, Hammal R, Benharref A, Hajbi AE, Mazoir N. 2016. A theoretical investigation of the reactivity and regioselectivity of triterpene derivatives using difference local index, Parr functions. Moroccan J Chem. 4(4):938–944.
   Google Scholar
• Zhao Y, Truhlar DG. 2004. Hybrid meta density functional theory methods for thermochemistry, thermochemical kinetics, and noncovalent interactions: The MPW1B95 and MPWB1K models and comparative assessments for hydrogen bonding and van der Waals interactions. J Phys Chem A. 108(33):6908–6918.
   Web of Science ®Google Scholar