Synthesis, Characterization, Biological, and Antioxidant Activity of New Metal Ion Complexes with Schiff Base Derived from 2-Hydroxybenzohydrazide

https://doi.org/10.22146/ijc.98292

Ayyat Jawad Kadhim(1*), Naser Shaalan(2)

(1) Department of Chemistry, College of Science for Women, University of Baghdad, Baghdad 10071, Iraq
(2) Department of Chemistry, College of Science for Women, University of Baghdad, Baghdad 10071, Iraq
(*) Corresponding Author

Abstract


The study involved the synthesis of new complexes with tetradentate ligand (LH). The general formula of complexes was [M(LH)(H2O)2] with M of Ni+2, Co+2, Cu+2, and Zn+. The ligand was synthesized by treating the 2-hydroxybenzohydrazide with salicylaldehyde. The structural characteristics of ligands and complexes were analyzed using various techniques, including elemental analyses, magnetic susceptibility, molar conductivity, infrared, ultraviolet absorption, mass, and NMR spectroscopy studies. The physical measurements indicated that the prepared complexes are non-electrolyte and showed that the ligand is tetradentate when coordinated with metal ions through the nitrogen of azomethine (–C=N–), two oxygen atoms of O–H phenolic, and an oxygen atom of carbonyl (C=O) for benzohydrazide. It was found that Co+2, Cu+2, and Zn+2 complexes are octahedral, while Ni+2 complexes are square planar. The biological screening of the complexes demonstrates that the Schiff base metal complexes exhibit remarkable efficacy in combating microorganisms by utilizing Gram-positive bacteria (Bacillus subtilis and Staphylococcus aureus) and Gram-negative bacteria (Pseudomonas aeruginosa and Escherichia coli) bacteria, as well as Candida albicans fungi. Hence, their results were good in inhibition. Then, the potential of these prepared compounds as antioxidants was determined by inhibiting free radicals.

Keywords


antioxidant; biological activity; 2-hydroxybenzohydrazide; Schiff base metal complexes



References

[1] Omidi, S., and Kakanejadifard, A., 2020, A review on biological activities of Schiff base, hydrazone, and oxime derivatives of curcumin, RSC Adv., 10 (50), 30186–30202.

[2] Ghanghas, P., Choudhary, A., Kumar, D., and Poonia, K., 2021, Coordination metal complexes with Schiff bases: Useful pharmacophores with comprehensive biological applications, Inorg. Chem. Commun., 130, 108710.

[3] 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), 642–642.‏

[4] 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.

[5] Yousif, E., Majeed, A., Al-Sammarrae, K., Salih, N., Salimon, J., and Abdullah, B., 2017, Metal complexes of Schiff base: Preparation, characterization and antibacterial activity, Arabian J. Chem., 10, S1639–S1644.

[6] More, M.S., Joshi, P.G., Mishra, Y.K., and Khanna, P.K., 2019, Metal complexes driven from Schiff bases and semicarbazones for biomedical and allied applications, Mater. Today Chem., 14, 100195.

[7] Hassan, S.A., Lateef, S.M., and Majeed, I.Y., 2020, Structural, spectral and thermal studies of new bidentate Schiff base ligand type (NO) derived from mebendazol and 4-aminoantipyrine and it's metal complexes and evaluation of their biological activity, Res. J. Pharm. Technol., 13 (6), 3001–3006.

[8] 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.

[9] Sani, U., and Dailami, S.A., 2015, Synthesis, characterization, antimicrobial activity and antioxidant studies of metal(II) complexes of Schiff base derived from 2–hydroxy-1-naphthaldehyde and hydrazine monohydrate, ChemSearch J., 6 (2), 35–41.

[10] Tomma, J.H., Khazaal, M.S., and Al-Dujaili, A.H., 2014, Synthesis and characterization of novel Schiff bases containing pyrimidine unit, Arabian J. Chem., 7 (1), 157–163.

[11] Jamain, Z., Azman, A.N.A., Razali, N.A., and Makmud, M.Z.H., 2022, A review on mesophase and physical properties of cyclotriphosphazene derivatives with Schiff base linkage, Crystals, 12 (8), 1174.

[12] Al Zoubi, W., Mohamed, S.G., Al-Hamdani, A.A.S., Mahendradhany, A.P., and Ko, Y.G., 2018, Acyclic and cyclic imines and their metal complexes: Recent progress in biomaterials and corrosion applications, RSC Adv., 8 (41), 23294–23318.

[13] Verma, C., Thakur, A., Ganjoo, R., Sharma, S., Assad, H., Kumar, A., Quraishi, M.A., and Alfantazi, A., 2023, Coordination bonding and corrosion inhibition potential of nitrogen-rich heterocycles: Azoles and triazines as specific examples, Coord. Chem. Rev., 488, 215177.

[14] Nafee, S.S., Hagar, M., Ahmed, H.A., El-Shishtawy, R.M., and Raffah, B.M., 2019, The synthesis of new thermal stable Schiff base/ester liquid crystals: A computational, mesomorphic, and optical study, Molecules., 24 (17), 3032.

[15] Shen, Y., and Dierking, I., 2019, Perspectives in liquid-crystal-aided nanotechnology and nanoscience, Appl. Sci., 9 (12), 2512.

[16] Mazzoni, R., Roncaglia, F., and Rigamonti, L., 2021, When the metal makes the difference: Template syntheses of tridentate and tetradentate salen-type Schiff base ligands and related complexes, Crystals, 11 (5), 483.

[17] Pradeep, C.P., and Das, S.K., 2013, Coordination and supramolecular aspects of the metal complexes of chiral N-salicyl-β-amino alcohol Schiff base ligands: Towards understanding the roles of weak interactions in their catalytic reactions, Coord. Chem. Rev., 257 (11-12), 1699–1715.

[18] Antony, R., Arun, T., and Manickam, S.T.D., 2019, A review on applications of chitosan-based Schiff bases, Int. J. Biol. Macromol., 129, 615–633.

[19] Alfonso‐Herrera, L.A., Rosete‐Luna, S., Hernández‐Romero, D., Rivera‐Villanueva, J.M., Olivares‐Romero, J.L., Cruz‐Navarro, J.A., Soto‐Contreras, A., Arenaza‐Corona, A., Morales‐Morales, D., and Colorado‐Peralta, R., 2022, Transition metal complexes with tridentate schiff bases (O N O and O N N) derived from salicylaldehyde: an analysis of their potential anticancer activity, ChemMedChem, 17 (20), e202200367.

[20] Ibraheem, H., Al-Majedy, Y., and Al-Amiery, A., 2018, 4-Thiadiazole: The biological activities, Syst. Rev. Pharm., 9 (1), 36–40.

[21] Hussein, N.A., and Abbas, A.K., 2022, Synthesis, spectroscopic characterization and thermal study of some transition metal complexes derived from caffeine azo ligand with some of their applications, Eurasian Chem. Commun., 4 (1), 67–93.

[22] Fekri, R., Salehi, M., Asadi, A., and Kubicki, M., 2019, Synthesis, characterization, anticancer and antibacterial evaluation of Schiff base ligands derived from hydrazone and their transition metal complexes, Inorg. Chim. Acta, 484, 245–254.

[23] Balouiri, M., Sadiki, M., and Ibnsouda, S.K., 2016, Methods for in vitro evaluating antimicrobial activity, J. Pharm. Anal., 6 (2), 71–79.

[24] Arifiyanto, A., and Farisi, S., 2023, Antioxidant activity of endophytic bacteria isolated from (Pyrrosia piloselloides) (L) MG Price, Baghdad Sci. J., 20 (6), 2177–2186.

[25] El-Gammal, O.A., El-Bindary, A.A., Sh. Mohamed, F., Rezk, G.N., and El-Bindary, M.A., 2022, Synthesis, characterization, design, molecular docking, anti COVID-19 activity, DFT calculations of novel Schiff base with some transition metal complexes, J. Mol. Liq., 346, 117850.

[26] Al-Dabbagh, A., Guo, Z., Junk, P., and Wang, J., 2021, Synthesis and characterization of a range of antimony(I/III) N,N-bis(2,6-diisopropylphenyl)formamidinate complexes, Acta Crystallogr., Sect. C: Struct. Chem., 77 (9), 577–585.

[27] Ayad Abd AL-Qadir, N., and Dheyaa Shaalan, N., 2023, Synthesis, characterization, and biological activity of new metal ion complexes with Schiff base (Z)-3((E)-2-hydroxybenzylidene) hydrazineylidene) indolin-2-one, J. Med. Chem. Sci., 6 (7), 1660–1674.

[28] Azzouz, A.S.P., and Ali, R.T., 2010, Synthesis of Schiff bases derived from benzaldehyde and salicylaldehyde with some amino acids by a new develop method, Iraqi Natl. J. Chem., 10 (37), 158–168.

[29] Yousfi, T., Elliott, A., Hanane, M., Merdes, R., and Moyano, A., 2016, Expedient organocatalytic syntheses of 4-substituted pyrazolidines and isoxazolidines, Molecules, 21 (12), 1655.

[30] Fadhil, A.E., and Abbas, A.K., 2023, Synthesis and structural views on new azo ligand and its metal complexes with some of their application, Iraqi J. Sci., 64 (12), 6119–6134.

[31] Shaalan, N., Khalaf, W.M., and Mahdi, S., 2022, Preparation and characterization of new tetra-dentate N2O2 Schiff base with some of metal ions complexes, Indones. J. Chem., 22 (1), 62–71.

[32] Al-Khateeb, Z.T., Karam, F.F., and Al-Adilee, K., 2019, Synthesis and characterization of some metals complexes with new heterocyclic azo dye ligand 2-[2-(5-nitro thiazolyl) azo]-4-methyl-5-nitro phenol and their biological activities, J. Phys.: Conf. Ser., 1294 (5), 052043.

[33] Rajakkani, P., Alagarraj, A., and Gurusamy Thangavelu, S.A., 2021, Tetraaza macrocyclic Schiff base metal complexes bearing pendant groups: Synthesis, characterization and bioactivity studies, Inorg. Chem. Commun., 134, 108989.

[34] 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.

[35] Xu, W., Liu, Z., Li, B., Li, G., and Liu, P., 2022, Effects of magnetic field force in preparation of plasma electrolytic oxidation coatings: A novel method to improve the corrosion resistance of magnesium, J. Alloys Compd., 906, 162642.

[36] Hammoda, R.G., and Shaalan, N., 2024, Synthesis, spectroscopy and biological activity study of some new complexes with Schiff base derived from malonic acid dihydrazide with 2-pyridine crboxaldehyde, Baghdad Sci. J., 21 (5), 1577–1591.

[37] Basheer, N.S., Kumar, B.R., Kurian, A., and George, S.D., 2015, Thermal conductivity measurement of organic solvents incorporated with silver nanoparticle using photothermal techniques, IOP Conf. Ser.: Mater. Sci. Eng., 73 (1), 012039.

[38] Echekwube, H.O., Ukoha, P.O., Ujam, O.T., Nwuche, C.O., Asegbeloyin, J.N., and Ibezim, A., 2019, Synthesis and in silico investigation of Schiff base derivatives of 1H-indole-2,3-diones and their Co(II) and Ni(II) complexes as antimicrobial agents, Braz. J. Biol. Sci., 6 (12), 63–85.

[39] Oguntoye, O.S., Hamid, A.A., Iloka, G.S., Bodede, S.O., Owalude, S.O., and Tella, A.C., 2016, Synthesis and spectroscopic analysis of Schiff bases of imesatin and isatin derivatives, J. Appl. Sci. Environ. Manage., 20 (3), 653–657.

[40] Uddin, M.N., Ahmed, S.S., and Alam, S.M.R., 2020, Biomedical applications of Schiff base metal complexes, J. Coord. Chem., 73 (23), 3109–3149.

[41] Oiye, É.N., Ribeiro, M.F.M., Katayama, J.M.T., Tadini, M.C., Balbino, M.A., Eleotério, I.C., Magalhães, J., Castro, A.S., Silva, R.S.M., da Cruz Júnior, J.W., and Dockal, E.R., 2019, Electrochemical sensors containing Schiff bases and their transition metal complexes to detect analytes of forensic, pharmaceutical and environmental interest. A review, Crit. Rev. Anal. Chem., 49 (6), 488–509.

[42] Hammoda, R.G., and Shaalan, N., 2023, Synthesis of Zn(II) and Co(II) complexes with a Schiff base derived from malonic acid dihydrazide for photo-stabilizers of polystyrene, Indones. J. Chem., 23 (5), 1324–1340.

[43] Kargar, H., Aghaei-Meybodi, F., Behjatmanesh-Ardakani, R., Elahifard, M.R., Torabi, V., Fallah-Mehrjardi, M., Tahir, M.N., Ashfaq, M., and Munawar, K.S., 2021, Synthesis, crystal structure, theoretical calculation, spectroscopic and antibacterial activity studies of copper(II) complexes bearing bidentate schiff base ligands derived from 4-aminoantipyrine: Influence of substitutions on antibacterial activity, J. Mol. Struct., 1230, 129908.

[44] Shaalan, N., 2022, Preparation and spectroscopic study, biological and thermodynamic activity of new complexes of some metal ions with 2-[5-(2-hydroxy-phenyl)-4,3,1-thiadiazol-2-ylimino]-methyl-naphthalene-1-ol, Baghdad Sci. J., 19 (4), 829–837.

[45] Saleh, R.H., Rashid, W.M., Dalaf, A.H., Al-Badrany, K.A., and Mohammed, O.A., 2020, Synthesis of some new thiazolidinone compounds derived from Schiff bases compounds and evaluation of their laser and biological efficacy, Ann. Trop. Public Health, 23 (7), 1012–1031.

[46] Umamaheswari, M., and Chatterjee, T.K., 2008, In vitro antioxidant activities of the fractions of Coccinia grandis L. leaf extract, Afr. J. Tradit., Complementary Altern. Med., 5 (1), 61–73.

[47] 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.

[48] Akram, E., Shaalan, N., Rashad, A.A., Hasan, A., Al-Amiery, A., and Yousif, E., 2016, Study of structural and optical properties of new films derived PVC-2-[5-phenyl-1,3,4-thiadiazol-2-ylimino-methyl]-benzoic acid, Res. J. Pharm., Biol. Chem. Sci., 7 (5), 2836–2844.

[49] Sami, S., and Shaalan, N., 2024, Synthesis, structure, and biological activity studies of new metal ion complexes based on 3-[(3-hydroxynaphthalene-2-yl-ethylidene)-hydrazono]-1,3-dihydro-indol-2-one, Indones. J. Chem., 24 (2), 370–378.



DOI: https://doi.org/10.22146/ijc.98292

Article Metrics

Abstract views : 52 | views : 18 | views : 32


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.