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

https://doi.org/10.22146/ijc.87359

Safa Sami(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


In the present study, a novel ligand (L) made of 2-hydroxynaphthaldehyde and 3-hydrazone-1,3-dihydro-indole-2-one(3-[(3-hydroxynaphthalen-2-yl-ethylidene)-hydrazono]-1,3-dihydro-indol-2-one). The ligand was characterized by FTIR, UV-vis, mass, 1H-NMR, 13C-NMR, and CHN elemental analysis. New complexes of this ligand were created by treating methanol and a drop of DMF solution of the produced ligand with the hydrated metal salts of Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) in a molar ratio of 2:1 (L:M). As a result, complexes have been emerged and identified FTIR, UV-vis, C.H.N., chloride-containing, molar conductance, magnetic susceptibility, and atomic absorption. The characterization result for each complex indicated complexes with octahedral coordination geometry and tridentates with metal to ligand ratios of 1:2. The biological activities of the new compounds were examined against Gram-negative bacteria (Escherichia coli) and Gram-positive bacteria (Staphylococcus aureus) giving an acceptable inhibition efficiency.


Keywords


biological activities; isatin; metal complexes; Schiff base; 2-hydroxynaphthaldehyde



References

[1] Isyaku, S., Aliyu, H.N., Ozoro, E.C., and Abubakar, T., 2019, Synthesis, characterization and antimicrobial studies of Mn(II) complexes of acetylthiophene and acetylfuran Schiff base derivatives, Bayero J. Pure Appl. Sci., 12 (1), 85–92.

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

[3] Khachatryan, G.E., Mkrtchyan, N.I., and Gavalyan, V.B., 2018, Antibacterial properties of new chitosan based Schiff-base, Int. J. Adv. Res., 6 (7), 1187–1192.

[4] Zhang, X., Shen, L.Y., Zhang, Q.L., Yang, X.J., Huang, Y.L., Redshaw, C., and Xu, H., 2021, A simple turn-off Schiff base fluorescent sensor for copper(II) ion and its application in water analysis, Molecules, 26 (5), 1233.

[5] Bassanetti, I., Atzeri, C., Tinonin, D.A., and Marchio, L., 2016, Silver(I) and thioether-bis(pyrazolyl)methane Ligands: The correlation between ligand functionalization and coordination polymer architecture, Cryst. Growth Des., 16 (6), 3543–3552.

[6] 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.

[7] Satpati, S., Saha, S.K., Suhasaria, A., Banerjee, P., and Sukul, D., 2020, Adsorption and anti-corrosion characteristics of vanillin Schiff bases on mild steel in 1 M HCl: Experimental and theoretical study, RSC Adv., 16 (10), 9258–9273.

[8] Shaalan, N.D., and Abdulwahhab, S., 2021, Synthesis, characterization and biological activity study of some new metal complexes with Schiff’s bases derived from [o-vanillin] with [2-amino-5-(2-hydroxy-phenyl)-1,3,4-thiadiazole], Egypt. J. Chem., 64 (8), 4059–4067.

[9] 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.

[10] 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.

[11] Iacopetta, D., Lappano, R., Mariconda, A., Ceramella, J., Sinicropi, M.S., Saturnino, C., Talia, M., Cirillo, F., Martinelli, F., Puoci, F., Rosano, C., Longo, P., and Maggiolini, M., 2020, Newly synthesized imino-derivatives analogues of resveratrol exert inhibitory effects in breast tumor cells, Int. J. Mol. Sci., 21 (20), 7797.

[12] Salam, B., El-Hiti, G.A., Bufaroosha, M., Ahmed, D.S., Ahmed, A., Alotaibi, M.H., and Yousif, E., 2020, Tin complexes containing an atenolol moiety as photostabilizers for poly(vinyl chloride), Polymers, 12 (12), 2923.

[13] Catalano, A., Sinicropi, M.S., Iacopetta, D., Ceramella, J., Mariconda, A., Rosano, C., Scali, E., Saturnino, C., and Longo, P., 2021, A review on the advancements in the field of metal complexes with Schiff bases as antiproliferative agents, Appl. Sci., 11 (13), 6027.

[14] Abd AL-Qadir, N.A., and Shaalan, N.D., 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.

[15] Arief, M.M.H., Ahmed, M.H.M., Said, A.A., and Selim, N.M.M., 2013, Synthesis of some heterocyclic compounds based on (2,3-dioxo-2,3-dihydro-1H-indol-1-yl) acetyl acetic acid derivatives, Int. J. Basic Appl. Sci., 2 (2), 153–159.

[16] 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.

[17] 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), 829–837.

[18] Obaid, S.M., Jarad, A.J. and Al-Hamdani, A.A.S., 2020, Synthesis, characterization and biological activity of mixed ligand metal salts complexes with various ligands, J. Phys.: Conf. Ser., 1660 (1), 012028.

[19] Abd Dleam, E., and Kareem, S.H., 2021, Mesoporous silica nanoparticles as a system for ciprofloxacin drug delivery kinetic of adsorption and releasing, Baghdad Sci. J., 18 (2), 357–365.

[20] Hassan S.S., Hassan, N.M., Baqer, S.R., and Saleh, A.M., 2021, Biological evaluation and theoretical study of bi-dentate ligand for amoxicillin derivative with some metal ions, Baghdad Sci. J., 18 (4), 1269–1278.

[21] 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.

[22] 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., Dockal, E.R., and de Oliveira, M.F., 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.

[23] Geary, W.J., 1971, The use of conductivity measurements in organic solvents for the characterization of coordination compounds, Coord. Chem. Rev., 7 (1), 81–122.

[24] Ali, I., Wani, A.W., and Saleem, K., 2013, Empirical formulae to molecular structures of metal complexes by molar conductance, Synth. React. Inorg., Met.-Org., Nano-Met. Chem., 43 (9), 1162–1172.

[25] Swamy, S.J., and Pola, S., 2008, Spectroscopic studies on Co(II), Ni(II), Cu(II) and Zn(II) complexes with a N4-macrocylic ligands, Spectrochim. Acta, Part A, 70 (4), 929–933.

[26] Halli, M.B., and Sumathi, R.B., 2017, Synthesis, physico-chemical investigations and biological screening of metal(II) complexes with Schiff base derived from naphthofuran-2-carbohydrazide and citral, Arabian J. Chem., 10, S1748–S1759.

[27] Omar, M.M., Abd El‐Halim, H.F., and Khalil, E.A.M., 2017, Synthesis, characterization, and biological and anticancer studies of mixed ligand complexes with Schiff base and 2,2′‐bipyridine, Appl. Organomet. Chem., 31 (10), e3724.

[28] Abbas, A.K., 2016, Preparation, characterization and biological evaluation of some lanthanide(ΙΙΙ) ions complexes with 3-(1-methyl-2-benzimidazolylazo)-tyrosine, Baghdad Sci. J., 13 (Suppl. 2), 128–142.

[29] Taha, Z.A., Ajlouni, A.M., Al-Hassan, K.A., Hijazi, A.K. and Faiq, A.B., 2011, Syntheses, characterization, biological activity and fluorescence properties of bis-(salicylaldehyde)-1, 3-propylenediimine Schiff base ligand and its lanthanide complexes, Spectrochim. Acta, Part A, 81 (1), 317–323.



DOI: https://doi.org/10.22146/ijc.87359

Article Metrics

Abstract views : 143 | views : 54 | views : 30


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.