Microwave-Assisted, Preparation, Characterization, and Biological Activities of Schiff Bases Derived from 4-Aminoantipyrine with Acetonyl Acetone for Some New Rare-Earth Metals

https://doi.org/10.22146/ijc.95419

Kawther Adeeb Hussein(1*), Naser Shaalan(2), Marwa Faeq(3)

(1) Department of Chemistry, College of Science, Al-Nahrain University, Jadria, Baghdad 10072, Iraq
(2) Department of Chemistry, College of Science for Women, University of Baghdad, Baghdad 10071, Iraq
(3) Department of Chemistry, College of Science, Al-Nahrain University, Jadria, Baghdad 10072, Iraq
(*) Corresponding Author

Abstract


Five new lanthanide complexes based on azomethine (Schiff bases) ligands have been synthesized, including La, Nd, Er, Gd, and Dy. Complexes were synthesized using the azomethine Schiff bases resulting from condensation reactions between 4-aminoantipyrine and acetonylacetone. The structural characteristics of azomethine obtained are characterized quantitatively and qualitatively through various techniques, including elemental analyses, magnetic susceptibility measurement, molar conductivity, infrared, ultraviolet absorption, GC-mass, and 1H- and 13C-NMR spectroscopy studies. The structural characteristics of Ln+3 complexes indicate that the complexes possess a composition of a specific type. Based on the elemental analyses, magnetic susceptibility measurement, molar conductivity, and ultraviolet absorption spectroscopy data, it can be inferred that the central metal ion is surrounded by a coordination number of 10, the general formula of [Ln(L)2(NO3)]·nNO3nH2O. The physical measurements confirmed that the synthesized complexes exhibit non-electrolyte behavior and paramagnetic properties. The antibacterial activity of the compounds was assessed in vitro against 4 pathogenic strains: E. coli, S. aureus, K. pneumoniae, and S. mutans. The evaluation was conducted using the agar disc spreading method. The results demonstrated that certain complexes exhibited significant antibacterial efficacy in comparison to the biological activity of the ligand.


Keywords


Schiff base; lanthanide; biological activity; microwave; 4-aminoantipyrine



References

[1] Singh, C., Khanna, V., and Singh, S., 2023, Sustainability of microwave heating in materials processing technologies, Mater. Today: Proc., 73, 241–248.

[2] Margetic, D., 2024, Mechanochemical and microwave multistep organic reactions, Curr. Green Chem., 11 (2), 172–193.

[3] Zhang, Y., 2017, The Application of Microwave Technology in Chemistry and Chemical Engineering, Proceedings of the 2016 International Conference on Engineering Management, Atlantis Press, Dordrecht, Netherlands, 50–53.

[4] Taha, Z.A., Hijazi, A.K., and Al Momani, W.M., 2020, Lanthanide complexes of the tridentate Schiff base ligand salicylaldehyde-2-picolinoylhydrazone: Synthesis, characterization, photophysical properties, biological activities and catalytic oxidation of aniline, J. Mol. Struct., 1220, 128712.

[5] Soliman, A.I.A., Sayed, M., Elshanawany, M.M., Younis, O., Ahmed, M., Kamal El-Dean, A.M., Abdel-Wahab, A.M.A., Wachtveitl, J., Braun, M., Fatehi, P., and Tolba, M.S., 2022, Base-free synthesis and photophysical properties of new Schiff bases containing indole moiety, ACS Omega, 7 (12), 10178–10186.‏

[6] Boulechfar, C., Ferkous, H., Delimi, A., Djedouani, A., Kahlouche, A., Boublia, A., Darwish, A.S., Lemaoui, T., Verma, R., and Benguerba, Y., 2023, Schiff bases and their metal complexes: A review on the history, synthesis, and applications, Inorg. Chem. Commun., 150, 110451.

[7] Hussain, E.M., 2023, Synthesis and antibacterial evaluation for some new schiff-bases derived from p-amino acetanilide, Baghdad Sci. J., 20 (6), 2455–2455.

[8] Kargar, H., Fallah-Mehrjardi, M., and Munawar, K.S., 2024, Metal complexes incorporating tridentate ONO pyridyl hydrazone Schiff base ligands: Crystal structure, characterization and applications, Coord. Chem. Rev., 501, 215587.‏

[9] Abd AL_Qadir, N.A., and Shaalan, N.D., 2023, Synthesis, characterization and biological activity study for some new metals complexes with (3Z, 3'E)-3,3'-(((2E,5E)-hexane-2,5-diylidene)bis(hydrazine-2,1-diylidene))bis(indolin-2-one), Ibn AL-Haitham J. Pure Appl. Sci., 36 (3), 231–244.

[10] Yimer, A.M., 2015, Review on preparation and description of some first series divalent transition metal complexes with novel Schiff’s base ligands, Rev. Catal., 2 (1), 14–25.‏

[11] Kumar, R., Singh, A.A., Kumar, U., Jain, P., Sharma, A.K., Kant, C., and Haque Faizi, M.S., 2023, Recent advances in synthesis of heterocyclic Schiff base transition metal complexes and their antimicrobial activities especially antibacterial and antifungal, J. Mol. Struct., 1294, 136346.

[12] Al-Adilee, K.J., Jawad, S.H., Kyhoiesh, H.A.K., and Hassan, H.M., 2024, Synthesis, characterization, biological applications, and molecular docking studies of some transition metal complexes with azo dye ligand derived from 5-methyl imidazole, J. Mol. Struct., 1295, 136695.

[13] Gomaa, A.I., Gomaa, E.A., Zaky, R.R., and Abd El-Hady, M.N., 2024, Design and synthesis of pyridine bis-hydrazone metal complexes of Co(II), Cu(II), and Hg(II): Spectral, Gaussian, electrochemical, biological, drug-likeness and molecular docking investigations, Inorg. Chem. Commun., 162, 112188.

[14] Mohan, B., and Shaalan, N., 2023, Synthesis, spectroscopic, and biological activity study for new complexes of some metal ions with Schiff bases derived from 2-hydroxy naphthaldehyde with 2-amine benzhydrazide, Ibn Al-Haitham J. Pure Appl. Sci., 36 (1), 208–224.

[15] ‏Janjua, U.U., Pervaiz, M., Ali, F., Saleem, A., Ashraf, A., Younas, U., and Iqbal, M., 2023, Schiff base derived Mn(II) and Cd(II) novel complexes for catalytic and antioxidant applications, Inorg. Chem. Commun., 157, 111233.‏

[16] Kumar, M., Singh, A.K., Singh, V.K., Yadav, R.K., Singh, A.P., and Singh, S., 2024, Recent developments in the biological activities of 3d-metal complexes with salicylaldehyde-based N, O-donor Schiff base ligands, Coord. Chem. Rev., 505, 215663.

[17] Sakthivel, A., Jeyasubramanian, K., Thangagiri, B., and Raja, J.D., 2020, Recent advances in Schiff base metal complexes derived from 4-aminoantipyrine derivatives and their potential applications, J. Mol. Struct., 1222, 128885.

[18] Youns, N.M., 2024, Synthesis, characterization and antimicrobial activity of new 4-aminoantipyrine derivatives using ultrasonic mediation, Baghdad Sci. J., Online-First (9).

[19] Lal Singh, H., Kulhari, P., Choudhary, G., and Khaturia, S., 2024, Synthesis, spectral, DFT, and antibacterial studies of nickel(II) and cobalt(II) complexes with aminoantipyrine based Schiff base ligands, Inorg. Chem. Commun., 162, 112192.

[20] Narayanswamy, A., Ramakrishna, D., Shekar, P.V.R., Rajendrachari, S., and Sudhakar, R., 2024, Quantum chemical and experimental evaluation of a 4-amino-antipyrine based Schiff base as corrosion inhibitor for steel material, ACS Omega, 9 (11), 13262–13273.‏

[21] Ebosie, N.P., Ogwuegbu, M.O.C., Onyedika, G.O., and Onwumere, F.C., 2021, Biological and analytical applications of Schiff base metal complexes derived from salicylidene-4-aminoantipyrine and its derivatives: A review, J. Iran. Chem. Soc., 18 (12), 3145–3175.

[22] Hussein, K.A., and Shaalan, N., 2021, Synthesis, spectroscopy and biological activities studies for new complexes of some lanthanide metals with Schiff’s bases derived from dimedone with 4-aminoantipyrine, Chem. Methodol., 6 (2), 103–113.

[23] Shaalan, N., 2022, Preparation, spectroscopy, biological activities and thermodynamic studies of new complexes of some metal ions with 2-[5-(2-hydroxy-phenyl)-1,3,4-thiadiazol-2-ylimino]-methyl-naphthalen-1-Ol, Baghdad Sci. J., 19 (4), 0829–0829.

[24] Hussein, K.A., and Shaalan, N., 2022, Synthesis, characterization, and antibacterial activity of lanthanide metal complexes with Schiff base ligand produced from reaction of 4,4-methylene diantipyrine with ethylenediamine, Indones. J. Chem., 22 (5), 1365–1375.

[25] Bahjat, H.H., Ismail, R.A., Sulaiman, G.M., and Jabir, M.S., 2021, Magnetic field-assisted laser ablation of titanium dioxide nanoparticles in water for anti-bacterial applications, J. Inorg. Organomet. Polym. Mater., 31 (9), 3649–3656.

[26] Khashan, K.S., Abdulameer, F.A., Jabir, M.S., Hadi, A.A., and Sulaiman, G.M., 2020, Anticancer activity and toxicity of carbon nanoparticles produced by pulsed laser ablation of graphite in water, Adv. Nat. Sci: Nanosci. Nanotechnol., 11 (3), 035010.

[27] Khashan, K.S., Badr, B.A., Sulaiman, G.M., Jabir, M.S., and Hussain, S.A., 2021, Antibacterial activity of Zinc Oxide nanostructured materials synthesis by laser ablation method, J. Phys.: Conf. Ser., 1795 (1), 012040.

[28] Jihad, M.A., Noori, F.T.M., Jabir, M.S., Albukhaty, S., AlMalki, F.A., and Alyamani, A.A., 2021, Polyethylene glycol functionalized graphene oxide nanoparticles loaded with nigella sativa extract: A smart antibacterial therapeutic drug delivery system, Molecules, 26 (11), 3067.

[29] Mohammed, M.K.A., Mohammad, M.R., Jabir, M.S., and Ahmed, D.S., 2020, Functionalization, characterization, and antibacterial activity of single wall and multi wall carbon nanotubes, IOP Conf. Ser.: Mater. Sci. Eng., 757 (1), 012028.

[30] Ali, I.H., Jabir, M.S., Al-Shmgani, H.S.A., Sulaiman, G.M., and Sadoon, A.H., 2018, Pathological and immunological study on infection with Escherichia coli in ale BALB/c mice, J. Phys.: Conf. Ser., 1003 (1), 012009.

[31] Younus, A., Al-Ahmer, S., and Jabir, M., 2019, Evaluation of some immunological markers in children with bacterial meningitis caused by Streptococcus pneumoniae, Res. J. Biotechnol., 14, 131–133.

[32] Jabir, M.S., Rashid, T.M., Nayef, U.M., Albukhaty, S., AlMalki, F.A., Albaqami, J., AlYamani, A.A., Taqi, Z.J., and Sulaiman, G.M., 2022, Inhibition of Staphylococcus aureus α-hemolysin production using nanocurcumin capped Au@ZnO nanocomposite, Bioinorg. Chem. Appl., 2022 (1), 2663812.

[33] Wang, Y.F., 2021, Borinic Acid-Catalyzed Ring-Opening of Epoxy Alcohols, Dissertation, University of Toronto, Canada.

[34] Khalil, M.H., and Abdullah, F.O., 2024, Synthesis, characterization, and anticancer and antioxidant activities of novel complexes of palladium and an organic Schiff-base ligand, Bull. Chem. Soc. Ethiop., 38 (3), 605–613.

[35] Gavali, L.V., Mohammed, A.A., Al-Ogaili, M.J., Gaikwad, S.H., Kulkarni, M., Das, R., and Ubale, P.A., 2024, Novel terephthalaldehyde bis (thiosemicarbazone) Schiff base ligand and its transition metal complexes as antibacterial Agents: Synthesis, characterization and biological investigations, Results Chem., 7, 101316.

[36] Shaalan, N., Fadel, Z.H., Mahmood, W.A., and Al-Hamdani, A.A.S., 2016, Synthesis and characterization studies of metal complexes with Schiff base derived from 4-[5-(2-hydoxy-phenyl)-[1,3,4-oxadiazol-2-ylimino methyl]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one, Baghdad Sci. J., 13 (2), 19–28.‏

[37] Hussein, K.A., Shaalan, N., Lafta, A.K., and Al Akeedi, J.M., 2024, Preparation, characterization, and biological activity of La(III), Nd(III), Er(III), Gd(III), and Dy(III) complexes with Schiff base resulted from reaction of 4-antipyrinecarboxaldehyde and 2-aminobenzothiazole, Indones. J. Chem., 24 (2), 358–369.

[38] Abdulrazzaq, A.G., and Al-Hamdani, A.A.S., 2023, Ni2+, Pt4+, Pd2+, and Mn2+ metal ions complexes with azo derived from quinolin-2-ol and 3-amino-N-(5-methylisoxazol-3-yl) benzenesulfonamide: Synthesis, characterization, thermal study, and antioxidant activity, Baghdad Sci. J., 20 (6), 2207–2223.‏

[39] Hussein, K.A., Mahdi, S., and Shaalan, N., 2023, Synthesis, spectroscopy of new lanthanide complexes with Schiff base derived from (4-antipyrinecarboxaldehyde with ethylene di-amine) and study the bioactivity, Baghdad Sci. J., 20 (2), 469–482.

[40] Cruz-Navarro, A., Rivera, J.M., Durán-Hernández, J., Castillo-Blum, S., Flores-Parra, A., Sánchez, M., Hernández-Ahuactzi, I., and Colorado-Peralta, R., 2018, Luminescence properties and DFT calculations of lanthanide (III) complexes (Ln = La, Nd, Sm, Eu, Gd, Tb, Dy) with 2,6-bis (5-methyl-benzimidazol-2-yl)pyridine, J. Mol. Struct., 1164, 209–216.

[41] Li, M., Dong, H., Chen, Y., Hao, W., Wang, Y., Zhang, Y., Zhang, Z., Hao, Y., Zhou, Y., Li, F., and Liu, L., 2024, A dual-ligand lanthanide-based metal–organic framework for highly selective and sensitive colorimetric detection of Fe2+, Anal. Methods, 16 (6), 899–906.

[42] Evsiunina, M.V., Khult, E.K., Matveev, P.I., Kalle, P., Lemport, P.S., Petrov, V.S., Aksenova, S.A., Nelyubina, Y.V., Koshelev, D.S., Utochnikova, V.V., Petrov, V.G., Ustynyuk, Y.A., and Nenajdenko, V.G., 2024, Unravelling the mechanism of f-element extraction by phenanthroline-diamides: A case of 4,7-substituted 1,10-phenanthroline-2,9-diamides, Sep. Purif. Technol., 339, 126621.

[43] Sivakumar, R., and Lee, N.Y., 2024, Recent advances in luminescent lanthanides and transition metal complex-based probes for imaging reactive oxygen, nitrogen, and sulfur species in living cells, Coord. Chem. Rev., 501, 215563.‏

[44] Schwarz, N., Krätschmer, F., Suryadevara, N., Schlittenhardt, S., Ruben, M., and Roesky, P.W., 2024, Synthesis, structural characterization, and magnetic properties of lanthanide arsolyl sandwich complexes, Inorg. Chem., 63 (21), 9520–9526.

[45] Abdulrazzaq, A.G., and Al-Hamdani, A.A.S., 2024, Synthesis, characterization, thermal analysis study and antioxidant activity for some metal ions Cr(III), Fe(III), Mn(II) and Pd(II) complexes with azo dye derived from p-methyl-2-hydroxybenzaldehyde, Baghdad Sci. J.‏, 21 (6), 1960–1982.

[46] Gil, Y., and Aravena, D., 2024, Understanding Single-Molecule Magnet properties of lanthanide complexes from 4f orbital splitting, Dalton Trans., 53 (5), 2207–2217.

[47] Kim, T., Jeon, H., Lee, J.R., and Kim, D., 2024, Magnetic separation-enhanced photoluminescence detection of dipicolinic acid and quenching detection of Cu(II) ions, Spectrochim. Acta, Part A, 305, 123501.

[48] Al-Hamdani, A.A.S., Shaalan, N., Hassan, S.S., and Hasan, Z.A.A.H., 2016, Preparation and spectroscopic studies of some metal ion complexes of 2-((4-formyl-3-hydroxynaphthalen-2-yl) diazenyl) benzoic acid, Baghdad Sci. J., 13 (2), 95–104.‏

[49] Nassar, H., Abou-El-Wafa, M.H.M., and Elkik, H., 2024, Synthesis and characterization of some coordinated metal and charge transfer complexes of isonicotinic acid hydrazide ligand with 2-hydroxyacetophenonylidene, Spectrochim. Acta, Part A, 309, 123759.

[50] Arnaouti, E., Georgiadou, C., Hatizdimitriou, A.G., Kalogiannis, S., and Psomas, G., 2024, Erbium(III) complexes with fluoroquinolones: Structure and biological properties, J. Inorg. Biochem., 255, 112525.

[51] Iacopetta, D., Ceramella, J., Catalano, A., Mariconda, A., Giuzio, F., Saturnino, C., Longo, P., and Sinicropi, M.S., 2023, Metal complexes with Schiff bases as antimicrobials and catalysts, Inorganics, 11 (8), 320.

[52] Bayeh, Y., Mohammed, F., Gebrezgiabher, M., Elemo, F., Getachew, M., and Thomas, M., 2020, Synthesis, characterization, and antibacterial activities of polydentate Schiff bases, based on salicylaldehyde, Adv. Biol. Chem., 10 (5), 127–139.

[53] Abd El-Halim, H., El-Sayed, O.Y., and Mohamed, G.G., 2023, Anti-carcinoma and anti-microbial behavioral studies for octahedral synthesized Schiff base metal complexes, J. Iran. Chem. Soc., 20 (11), 2713–2725.

[54] Al-Hajjar, R.L.N., Taha, E.M., Farhan, A.M., and Shaalan, N., 2023, Enzymatic assay of immobilized β-D-galactosidase enzyme on magnetite nanoparticle, Iraqi J. Sci., 64 (2), 6093–6103.‏

[55] Reda, S.M., and Al-Hamdani, A.A.S., 2023, Mn(II), Fe(III), Co(II) and Rh(III) complexes with azo ligand: Synthesis, characterization, thermal analysis, and bioactivity, Baghdad Sci. J., 20 (3), 642–660.‏



DOI: https://doi.org/10.22146/ijc.95419

Article Metrics

Abstract views : 107 | views : 55 | views : 27


Copyright (c) 2024 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

 


Indonesian Journal of Chemistry (ISSN 1411-9420 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web
Analytics View The Statistics of Indones. J. Chem.