Study of dipolar 1.3 cycloaddition reaction by DFT method, as well as study of antibacterial activity of two isomers 1.4 and 1.5 on two therapeutic targets E. coli and Helicobacter pylori, by molecular docking

Year 2021, Volume: 5 Issue: 2, 46 - 55, 15.12.2021

Mohammed Aziz Ajana , Abdessadak Oumayma , Halima Hajjı , Yassıne Koubı , Tahar Lakhlıfı , Mohammed Bouachrıne

https://doi.org/10.33435/tcandtc.1020278

Cited By: 3

Abstract

A study was carried out on the 1.3 dipolar cycloaddition reaction between Phenylethyne and Benzyl (diazyn-1-ium-1-yl) azanide, using the different theoretical approaches, to know precisely the reaction path, and the regioselectivity of reaction, as well as the transition state. We carried out this study by using the DFT method on the one hand, on the other hand we studied the antibacterial activity of two isomers 1.4 and 1.5 obtained from cycloaddition reaction on two therapeutic targets E. coli and Helicobacter pylori, using Molecular docking.

Keywords

Cycloaddition, Isomer, Transition state, DFT, Molecular Docking.

References

• [1] Santelli, M.; Pons, J. M. Lewis Acids and Selectivity in Organic Synthesis. CRC Press, Boca Raton, (1996).
• [2] Padwa, A. 1,3-Dipolar Cycloaddition Chemistry. Wiley: New York, (1984).
• [3] Gothelf, K.V.; Jørgensen, K.A. Chem. Rev: Asymmetric 1,3-Dipolar Cycloaddition Reactions 98 (1998) 863–909. https://doi.org/10.1021/cr970324e
• [4] Padwa, A.; Pearson, W. H. Synthetic applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Naturel products. Wiley: New York, (2002).
• [5] Frederickson, M. Tetrahedron: Optically active isoxazolidines via asymmetric cycloaddition reactions of nitrones with alkenes: applications in organic synthesis 53 (1997) 403–425. https://doi.org/10.1016/S0040-4020(96)01095-2
• [6] Roberto, S.; Gomes, Guilherme A.M.; Jardim, Renato L,de Carvalho.; Maria H. Araujo.;Eufrânio N, da Silva Júnior. Beyond Copper-Catalyzed Azide-Alkyne 1,3-dipolar Cycloaddition: Synthesis and mechanism insights, (2019).
• [7] Kenneth, N.; Campbell, Barbara, K. Organic Syntheses: Phenylacetylene, 30, 72, (1950). https://doi:10.15227/orgsyn.030.0072.
• [8] HAJJI, Halima, et al. Antiproliferative Activity: Discovery of new Benzoxanthenes derivatives by Using Various Statistical Methods 2D/3D-QSAR and Molecular Docking. RHAZES: Green and Applied Chemistry, 12 (2021) 40-59.
• [9] Pearson, R.G. Hard and Soft acid and Bases. Dowden, Hutchinson and Ross: Stroudenburry, PA, (1973).
• [10] Epiotis, N.D.; Am, Chem, Soc, J. Regioselectivity of concerted cycloadditions 17 (1973) 5624–5632. https://doi.org/10.1021/ja00798a029
• [11] Parr, R. G.; Wang, W. Density Theory for atoms and Molecules. University Press: Oxford, (1989).
• [12] Robert, G.; Parr, László.; Szentpály, v.; and, Shubin Liu. Electrophilicity Index. Journal of the American Chemical Society 121 (9) (1999) 1922-1924. https://doi.org/10.1021/ja983494x
• [13] Yang, W.; Mortier, W.J.; Am, Chem, Soc, J. The use of global and local molecular parameters for the analysis of the gas-phase basicity of amines, 108 (19) (1986) 5708-11. https://doi. 10.1021/ja00279a008.
• [14] Eyring, H.; Polanyi, M.; Chem, Phys, J. The Journal of Chemical Physics: Energy Distribution Among Reagents and Products of Atomic Reactions 31, 1338 (1959). https://doi.org/10.1063/1.1730597
• [15] Eyring, H.; Chem, Phys, J. The Activated Complex in Chemical Reactions 3(107), (1935). https://doi.org/10.1063/1.1749604
• [16] Huisgen, R. Angew. Chem: 1.3-Dipolar cycloadditions 75 (1963) 604-637. https://doi.org/10.1002/anie.196305651
• [17] Woodward, R. B.; Hoffmann, Roald. Stereochemistry of Electrocyclic Reactions. Journal of the American Chemical Society. 87 (2): 395 (1965). https:// doi:10.1021/ja01080a054
• [18] Bonandi, E.; Christodoulou, M.S.; Fumagalli, G.; Perdicchia, D.; Rastelli, G.; Passarella, D. Drug Discovery Today: The 1,2,3-triazole ring as a bioisostere in medicinal chemistry. 22 (10) (2017) 1572‑1581. https://doi.10.1016/j.drudis.2017.05.014
• [19] Totobenazara, J.; Burke, A.J. New click-chemistry methods for 1,2,3-triazoles synthesis: recent advances and applications. Tetrahedron Letters. 56 (22): 28539 (2015).
• [20] Rasmussen, L.K.; Boren, B.C.; Fokin, V.V. Ruthenium-Catalyzed Cycloaddition of Aryl Azides and Alkynes. Org Lett. 9 (26) (2007) 5337‑9.
• [21] Kaper, J. B., J. P. Nataro and H. L. Mobley. "Pathogenic Escherichia coli." Nat Rev Microbiol 2(2) (2004) 123-140.