The synthesis, antimicrobial activity and theoretical calculations of 4-(4,5-diphenyl-1-(4-(phenyldiazenyl)phenyl)-1H-imidazol-2-yl)-N,N-dimethylaniline
DOI:
https://doi.org/10.24959/nphj.24.147Keywords:
imidazole, synthesis, microwave, ionic liquid catalysts, antimicrobial activity, theoretical calculations, stabilityAbstract
Aim. To synthesize 4-(4,5-diphenyl-1-(4-(phenyldiazenyl)phenyl)-1H-imidazol-2-yl)-N,N-dimethylaniline, as well as make theoretical calculations of its structure and study its antimicrobial properties.
Materials and methods. The synthesis procedures were performed in the presence of ionic liquid catalysts and under microwave conditions. The catalysts included 1-butyl-3-methylimidazolehydrosulfate, N-methylpyrrolidone perchlorate, and 1,4-dimethylpiperazinedihydrosulfate ionic liquids. Benzyl, ammonium acetate, p-aminoazobenzene and 4-(dimethylamino)benzaldehyde were taken as reagents. Ethanol was used as a solvent.
Results. The results of the conditions were compared and it was determined that the 1,4-dimethylpiperazinedihydrosulfate catalyst reacted under microwave conditions in a shorter time (19 min) with a higher yield (78.1 %). The structure of the compound synthesized was analyzed by 1H, 13C NMR and IR spectroscopy. The theoretical calculations of the compound were determined using the density functional theory (DFT/B3LYP) method with a basic set of 6-31G(d,p). The geometry of the structure was optimized, bond lengths, angle degrees were given, and important quantum chemical parameters, such as HOMO, LUMO orbitals, reactivity, stability, electrophilicity, electronegativity, chemical softness, chemical hardness were calculated. It was found that the compound had a high stability (∆E = 2.359 eV) and a high biological activity (ω = 5.754 eV). The antimicrobial activity of the sample against bacteria of S. aureus, E. coli, P. aeruginosa, K. pneumoniae, B. anthracoides and C. albicans fungus was studied.
Conclusions. In this work, 4-(4,5-diphenyl-1-(4-(phenyldiazenyl)phenyl)-1H-imidazol-2-yl)-N,N-dimethylaniline has been synthesized from benzyl, ammonium acetate, p-aminoazobenzene and 4-(dimethylamino)benzaldehyde in the presence of microwave and ionic liquid catalysts. It has been determined that 1,4-dimethylpiperazinedihydrosulfate catalyst reacts under microwave conditions in a shorter time (19 min) with a higher yield (78.1 %). The compound has been tested as an antimicrobial agent against bacteria of S. aureus, E. coli, P. aeruginosa, K. pneumoniae, B. anthracoides and C. albicans fungus, showing moderate and higher activity.
References
Siwach, A., Verma, P. K. (2021). Synthesis and therapeutic potential of imidazole containing compounds. BMC Chemistry, 15(1). doi:10.1186/s13065-020-00730-1.
Sharma, P., LaRosa, C., Antwi, J., Govindarajan, R., Werbovetz, K. A. (2021). Imidazoles as Potential Anticancer Agents: An Update on Recent Studies. Molecules, 26(14), 4213. doi:10.3390/molecules26144213.
Abdelhamid, A. A., Salah, H. A., Marzouk, A. A. (2019). Synthesis of imidazole derivatives: Ester and hydrazide compounds with antioxidant activity using ionic liquid as an efficient catalyst. Journal of Heterocyclic Chemistry, 57(2), 676-685. doi:10.1002/jhet.3808.
Refaat, H. M. (2010). Synthesis and anticancer activity of some novel 2-substituted benzimidazole derivatives. European Journal of Medicinal Chemistry, 45(7), 2949-2956. doi:10.1016/j.ejmech.2010.03.022.
Hamdi, A., Daoudi, W., Aaddouz, M., Azzouzi, M., Amhamdi, H., Elyoussfi, A. et al. (2024). Various Synthesis and Biological Evaluation of Some Tri-Tetra-Substituted Imidazoles Derivatives: A Review. Heliyon, 10(10), e31253. doi: 10.1016/j.heliyon.2024.e31253.
Mammadov, A. M. (2019). Synthesis of 1,2,4,5-tetrasubstituted imidazoles in the presence of 1,4-dimethylpiperaziniumdihydrosulfate catalyst and their antimicrobial activity. Processes of Petrochemistry and Oil Refining, 20(3), 256-260.
Nshimyumukiza, P., Van Den Berge, E., Delest, B., Mijatovic, T., Kiss, R., Marchand-Brynaert, J., Robiette, R. (2010). Synthesis and biological evaluation of novel imidazole-containing macrocycles. Tetrahedron, 66(25), 4515-4520. doi:10.1016/j.tet.2010.04.070.
Zang, H., Su, Q., Mo, Y., Cheng, B.-W., Jun, S. (2010). Ionic liquid [EMIM]OAc under ultrasonic irradiation towards the first synthesis of trisubstituted imidazoles. Ultrasonics Sonochemistry, 17(5), 749-751. doi:10.1016/j.ultsonch.2010.01.015.
Fulwa, V. K., Sahu, R., Jena, H. S., Manivannan, V. (2009). Novel synthesis of 2,4-bis(2-pyridyl)-5-(pyridyl)imidazoles and formation of N-(3-(pyridyl)imidazo[1,5-a]pyridine)picolinamidines: nitrogen-rich ligands. Tetrahedron Letters, 50(46), 6264-6267. doi:10.1016/j.tetlet.2009.09.002.
Kumar, D., Thomas, K. R. J. (2011). Optical properties of pyrene and anthracene containing imidazoles: Experimental and theoretical investigations. Journal of Photochemistry and Photobiology A: Chemistry, 218(1), 162-173. doi:10.1016/j.jphotochem.2010.12.018.
Jayabharathi, J., Thanikachalam, V., Srinivasan, N., Venkatesh Perumal, M. (2012). Fluorescence spectral studies of some imidazole derivatives. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 90, 125-130. doi:10.1016/j.saa.2012.01.030.
Zheng, Q., Li, X., Kurpiewska, K., Dömling, A. (2022). Synthesis of Tunable Fluorescent Imidazole-Fused Heterocycle Dimers. Organic Letters, 24, 28. doi:10.1021/acs.orglett.2c01642.
Sathiyanarayanan, S., Marikkannu, C., Palaniswamy, N. (2005). Corrosion inhibition effect of tetramines for mild steel in 1M HCl. Applied Surface Science, 241(3-4), 477-484. doi:10.1016/j.apsusc.2004.07.050.
Nnenna, W. O., Jonathan, O. B., Ekemini, B. I., Abiodun, O. E. (2015). Imidazole derivative as novel effective inhibitor of mild steel corrosion in aqueous sulphuric acid. American Journal of Physical Chemistry, 4(1), 1-9.
Mammadov, A. M. (2021). Synthesis of imidazole-based complexes and investigation of their bactericidal properties against Srb. Processes of Petrochemistry and oil Refining, 22(4), 537-545.
Məmmədov, A. M., Cəfərova, R. Ə., Əliyev, B. M., Məmmədova, R. R., Orucova, N. S. (2020). Üç və dördəvəzli imidazolların sintezi. Gənc tədqiqatçı, 4(1), 27-37.
Verma, B. K., Kapoor, S., Kumar, U., Pandey, S., Arya, P. (2017). Synthesis of new Imidazole Derivatives as effective Antimicrobial Agents. Indian Journal of Pharmaceutical and Biological Research, 5(01), 01-09. doi:10.30750/ijpbr.5.1.1.
Naureen, S., Ijaz, F., Munawar, M. A., Asif, N., Chaudhry, F., Ashraf, M., Khan, M. A. (2017). Synthesis of tetrasubstitutd imidazoles containing indole and their antiurease and antioxidant activities. Journal of the Chilean Chemical Society, 62(3), 3583-3587. doi:10.4067/s0717-97072017000303583.
Orujova, N., Mammadov, A., Jafarova, R., Yolchuyeva, U., Ahmadbayova, S. (2023). Synthesis and study of diphenyl and 4-(phenyldiazenyl)phenyl based tetrasubstituted imidazoles in the presence of ionic liquid catalysts. PPOR, 4(2), 235-245. doi:10.36719/1726-4685/94/235-245.
Abdullayev, Y., Abbasov, V., Ducati, L. C., Talybov, A., Autschbach, J. (2016). Ionic Liquid Solvation versus Catalysis: Computational Insight from a Multisubstituted Imidazole Synthesis in [Et2 NH2] [HSO4]. ChemistryOpen, 5(5), 460-469. doi: 10.1002/open.201600066.
Abbasov, V. M., Orujova, N. S., Jafarova, R. A., Mammadov, A. M., Ahmadbayova, S. F. (2024). Synthesis and theoretical calculations of 4[4,5-diphenyl-1-(4(phenyldiazenyl)phenyl)-1h-imidazol-2-yl]-phenol. Processes of Petrochemistry and Oil Refining, 1, 89. doi:10.62972/1726-4685.2024.1.89.
Parsaee, Z., Mohammadi, K., Ghahramaninezhad, M., Hosseinzadeh, B. (2016). A novel nano-sized binuclear nickel(ii) Schiff base complex as a precursor for NiO nanoparticles: synthesis, characterization, DFT study and antibacterial activity. New Journal of Chemistry, 40(12), 10569-10583. doi:10.1039/c6nj02642g.
Messaoudi, B., Benhadria, N., Attar, T. (2023). Theoretical insights on the relationship between detection limit and complex stability of oxine ligand. Turkish Computational and Theoretical Chemistry, 8(1), 65-79. doi:10.33435/tcandtc.1252038.
Marinho, M. M., Almeida-Neto, F. W. Q., Marinho, E. M., da Silva, L. P., Menezes, R. R. P. P. B., dos Santos, R. P. Et al. (2021). Quantum computational investigations and molecular docking studies on amentoflavone. Heliyon, 7(1), e06079. doi:10.1016/j.heliyon.2021.e06079.
Neese, F. (2011). The ORCA program system. WIREs Computational Molecular Science, 2(1), 73-78. doi:10.1002/wcms.81
Tabti, K., Sbai, A., Maghat, H., Lakhlifi, T., Bouachrine, M. (2023). Computational assessment of the reactivity and pharmaceutical potential of Novel Triazole Derivatives: An approach combining DFT calculations, molecular dynamics simulations, and molecular docking. Arabian Journal of Chemistry, 17, 1, P. 105376. doi:10.1016/j.arabjc.2023.105376.
Domingo, L., Ríos-Gutiérrez, M., Pérez, P. (2016). Applications of the Conceptual Density Functional Theory Indices to Organic Chemistry Reactivity. Molecules, 21(6), 748. doi:10.3390/molecules21060748.
Ríos‐Gutiérrez, M., Sousa, A. S., Domingo, L. R. (2023). Electrophilicity and Nucleophilicity Scales at Different DFT Computational Levels. Journal of Physical Organic Chemistry, 36. e4503. doi:10.1002/poc.4503.
Synthesis of complexes of oleic acid with alkylamines and theoretical study of their structures. (2023). PPOR, 24, 4. 831-842. https://doi.org/10.36719/1726-4685/96/831-842.
Monir, U. (2018). Thermodynamic, HOMO-LUMO, MEP and ADMET Studies of Metronidazole and its Modified Derivatives Based on DFT. Op Acc J Bio Eng Bio Sci, 3(1), 1-9.
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