Synthesis, Characterization and Antibacterial Activity Study of Cobalt(II), Nickel(II), Copper(II), Palladium(II), Cadmium(II) and Platinum(IV) Complexes with 4-Amino-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazole-3-thione

Waleed Abbas Jawad(1), Asim Alaa Abd Al-Hussein Balakit(2), Mahmoud Najim Abid Al-Jibouri(3*)

(1) Ministry of Education, Babylon Education Directorate, Hilla-Iraq
(2) College of Pharmacy, University of Babylon, Hilla-Iraq
(3) Mustansiriyah University, College of Science, Department of Chemistry,IRAQ
(*) Corresponding Author


New transition metal complexes of cobalt(II), nickel(II), copper(II), palladium(II), cadmium(II), and platinum(IV) with bidentate ligand 4-amino-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazole-3-thiol were synthesized and characterized by microelemental analyses (CHNS), Fourier-transform infrared (FT-IR), UV-Visible spectra, molar conductance, magnetic susceptibility and thermal analyses (TG-DSC). The ligand was synthesized by ring closure of potassium-2-(3,4,5-trimethoxybenzoyl) hydrazine carbodithioate with an excess amount of hydrazine, and then was acidified using hydrochloric acid. The ligand was used as Lewis bases to prepare metal complexes through the reaction of ratio (1:2) metal:ligand. The ligand was characterized by 1H-NMR and 13C-NMR and the previously described methods to identify the complexes. The results obtained from spectra and elemental analyses indicated the tetrahedral geometry around Cd(II) ion, square-planar for Cu(II) and Pd(II), and octahedral geometry around Co(II), Ni(II), and Pt(IV). All the metal complexes showed significant antibacterial activity in comparison with the free ligand. The antibacterial test of the platinum(IV) complex showed higher activity than other metal complexes against bacteria Staphylococcus aureus (G-positive) and Escherichia coli (G-negative).


1,2,4-triazole-3-thione derivatives; new metal complexes; antibacterial activity


[1] Sugiyarto, K.H., Louise, I.S.Y., and Wilujeng, S.S., 2020, Preparation and powder XRD analysis of tris(2,2’-bipyridine)nickel(II) trifluoroacetate, Indones. J. Chem., 20 (4), 833–841.

[2] Timur, İ., Kocyigit, Ü.M., Dastan, T., Sandal, S., Ceribası, A.O., Taslimi P., Gulcin, İ., Koparir, M., Karatepe, M., and Çiftçi, M., 2019, In vitro cytotoxic and in vivo antitumoral activities of some aminomethyl derivatives of 2,4-dihydro-3H-1,2,4-triazole-3-thiones-Evaluation of their acetylcholinesterase and carbonic anhydrase enzymes inhibition profiles, J. Biochem. Mol. Toxicol., 33 (1), e22239.

[3] Kaproń, B., Łuszczki, J.J., Płazińska, A., Siwek, A., Karcz, T., Gryboś, A., Nowak, G., Makuch-Kocka, A., Walczak, K., Langner, E., Szalast, K., Marciniak, S., Paczkowska, M., Cielecka-Piontek, J., Ciesla, L.M., and Plech, T., 2019, Development of the 1,2,4-triazole-based anticonvulsant drug candidates acting on the voltage-gated sodium channels. Insights from in-vivo, in-vitro, and in-silico studies, Eur. J. Pharm. Sci., 129, 42–57.

[4] Sugiyarto, K.H., Yunita, I., and Goodwin, H.A., 2020, Preparation, electronic properties, and powder-XRD structure analysis of 3,5-Bis(pyridin-2-yl)-H-1,2,4-triazoledichloridocopper(II), Indones. J. Chem., 20 (6), 1422–1429.

[5] Obaid, S.M.H., Sultan, J.S., and Al-Hamdani, A.A.S., 2020, Synthesis, characterization and biological efficacies from some new dinuclear metal complexes for base 3-(3,4-dihydroxy-phenyl)-2-[(2-hydroxy-3-methylperoxybenzylidene)-amino]-2-methyl propionic acid, Indones. J. Chem., 20 (6), 1311–1322.

[6] Rasyda, Y.A., Widowati, M.K., Marliyana, S.D., and and Rahardjo, S.B., 2021, Synthesis, characterization and antibacterial properties of nickel(II) complex with 4-aminoantipyrine ligand, Indones. J. Chem., 21 (2), 391–399.

[7] Idrees, M., Nasare, R.D., and Siddiqui, N.J., 2016, Synthesis of S-phenacylated trisubstituted 1,2,4-triazole incorporated with 5-(benzofuran-2-yl)-1-phenyl-1H-pyrazol-3-yl moiety and their antibacterial screening, Chem. Sin., 7 (4), 28–35.

[8] Özadalı, K., Özkanlı, F., Jain, S., Rao, P.P.N., and Velázquez-Martínez, C.A., 2012, Synthesis and biological evaluation of isoxazolo[4,5-d]pyridazin-4-(5H)-one analogues as potent anti-inflammatory agents, Bioorg. Med. Chem., 20 (9), 2912–2922.

[9] Kanagarajan, V., Thanusu, J., and Gopalakrishnan, M., 2011, Synthesis and in vitro microbiological evaluation of novel 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9,5′-spiro-1′,2′,4′-triazolidine-3′-thiones, Med. Chem. Res., 21 (12), 3965–3972.

[10] Dallavalle, F., Gaccioli, F., Franchi-Gazzola, R., Lanfranchi, M., Marchiò, L., Pellinghelli, M.A., and Tegoni, M., 2002, Synthesis, molecular structure, solution equilibrium, and antiproliferative activity of thioxotriazoline and thioxotriazole complexes of copper(II) and palladium(II), J. Inorg. Biochem., 92 (2), 95–104.

[11] Al-Masoudi, N.A., Abdullah, B.H., Essa, A.H., Loddo, R., and LaColla, P., 2010, Platinum and palladium-triazole complexes as highly potential antitumor agents, Arch. Pharm., 343 (4), 222–227.

[12] Kapri, K.P., Singar, S.B., Khanal, S., and Shakya, B., 2020, Synthesis of Schiff bases of 4-amino-5-(2-hydroxyphenyl)-4H-1,2,4-triazole-3-thiol as potent antimicrobial agents, Amrit Res. J., 1 (1), 29–36.‏

[13] Devkota, K., Pathak, G., and Shakya, B., 2020, Synthesis and evaluation of Schiff bases of 4-amino-5-(chlorine substituted phenyl)-4H-1,2,4-triazole-3-thione as antimicrobial agents, J. Nepal Chem. Soc., 41 (1), 26–35.‏

[14] Namratha, B., and Gaonkar, S.L., 2014, 1,2,4-Triazoles: Synthetic strategies and pharmacological profiles, Int. J. Pharm. Pharm. Sci., 6 (8), 73–80.

[15] Bharty, M.K., Bharti, A., Chaurasia, R., Chaudhari, U.K., Kushawaha, S.K., Sonkar, P.K., and Butcher, R.J., 2019, Synthesis and characterization of Mn(II) complexes of 4-phenyl(phenyl-acetyl)-3-thiosemicarbazide, 4-amino-5-phenyl-1,2,4-triazole-3-thiolate, and their application towards electrochemical oxygen reduction reaction, Polyhedron, 173, 114125.‏

[16] Murti, Y., Agnihotri, R., and Pathak, D., 2011, Synthesis, characterization and pharmacological screening of some substituted 1,2,3- & 1,2,4-triazoles, Am. J. Chem., 1 (2), 42–46.‏

[17] Majeed A.S., 2010, Synthesis, structure and antibacterial activity of some 2-amino-5-(2-acetyloxyphenyl)-1,3,4-thiadiazole complexes, Al Mustansiriya J. Sci., 21 (5), 195–204.

[18] Yousif, E., Hameed, A., and Ameer, A., 2005, Synthesis and characterization of complexes of some transition metals with 2-amino-5-(4-hexyloxyphenyl)-1,3,4-thiadiazole, J. Al-Nahrain Univ., 8 (1), 9–11.

[19] Narayana, B, and Gajendragad, M., 1997, Complexes of Zn(II), Pd(II), Hg(II), Pb(II), Cu(I),Ag(I), and Ti(I) with 4-amino-5-merccapto-3-(o-tolyloxymethyl)-1,2,4-troazol, Turk. J. Chem., 21 (1), 71–76.

[20] Sliverstein, R., Webster, F.X., and Kiemle, D.J., 2005, Spectrometric Identification of Organic Compounds, 7th Ed., John Wiley & Sons, Hoboken, New York.

[21] Flifel, I., and Kadhim, S., 2012, Synthesis and characterization of 1,3,4-oxadiazole derivatives with some new transition metal complexes, J. Kerbala Univ., 10 (3), 197–209.

[22] Abd El-Razek, S.E., El-Gamasy, S.M., Hassan, M., Abdel-Aziz, M.S., and Nasr, S.M., 2020, Transition metal complexes of a multidentate Schiff base ligand containing guanidine moiety: Synthesis, characterization, anticancer effect, and antimicrobial activity, J. Mol. Struct., 1203, 127381.‏

[23] Anacona, J.R., Ruiz, K., Loroño, M., and Celis, F., 2019, Antibacterial activity of transition metal complexes containing a tridentate NNO phenoxymethylpenicillin‐based Schiff base. An anti‐MRSA iron(II) complex, Appl. Organomet. Chem., 33 (4), e4744.‏

[24] Rapheal, P.F., Manoj, E., Kurup, M.R.P., and Fun, H.K., 2021, Nickel(II) complexes of N(4)-substituted thiosemicarbazones derived from pyridine-2-carbaldehyde: Crystal structures, spectral aspects and Hirshfeld surface analysis, J. Mol. Struct., 1237, 130362.‏

[25] Hamil, A., Khalifa, K.M., Almutaleb, A.A., and Nouradean, M.Q., 2020, Synthesis, characterization and antibacterial activity studies of some transition metal chelates of Mn(II), Ni(II) and Cu(II) with Schiff base derived from diacetylmonoxime with O-phenylenediamine, Adv. J. Chem. A, 3 (4), 524–533.‏

[26] Kargar, H., Torabi, V., Akbari, A., Behjatmanesh-Ardakani, R., Sahraei, A., and Tahir, M.N., 2020, Pd(II) and Ni(II) complexes containing an asymmetric Schiff base ligand: Synthesis, X-ray crystal structure, spectroscopic investigations and computational studies, J. Mol. Struct., 1205, 127642.‏

[27] Adachi, J., Mori, T., Inoue, R., Naito, M., Le, N.H.T., Kawamorita, S., and Ariga, K., 2020, Emission control by molecular manipulation of double‐paddled binuclear PtII complexes at the air‐water interface, Chem. Asian J., 15 (3), 406–414.‏

[28] Yang, Y.J., Li, Y.H., Liu, D., and Cui, G.H., 2020, A dual-responsive luminescent sensor based on a water-stable Cd(II)-MOF for the highly selective and sensitive detection of acetylacetone and Cr2O72− in aqueous solutions, CrystEngComm, 22 (7), 1166–1175.

[29] ‏Tenorio, K.V., Fortunato, A.B., Moreira, J.M., Roman, D., D’Oliveira, K.A., Cuin, A., Brasil, D.M., Pinto, L.M.C., Colman, T.A.D., and Carvalho, C.T., 2020, Thermal analysis combined with X-ray diffraction/Rietveld method, FT-IR and UV-vis spectroscopy: Structural characterization of the lanthanum and cerium(III) polycrystalline complexes, Thermochim. Acta, 178662.‏

[30] Djunaidi, M.C., Setiyo, P.D., Lusiana, R.A., and Anggun Y., 2020, In-situ ionic imprinted membrane (IIM) synthesis based on acetic polyeugenoxy acetyl tiophen methanolate for gold(III) metal ion transports, Indones. J. Chem., 20 (6), 1323–1331.

[31] Bisceglie, F., Bacci, C., Vismarra, A., Barilli, E., Pioli, M., Orsoni, N., and Pelosi, G., 2020, Antibacterial activity of metal complexes based on cinnamaldehyde thiosemicarbazone analogues, J. Inorg. Biochem., 203, 110888.


Article Metrics

Abstract views : 1466 | views : 1199 | views : 572

Copyright (c) 2021 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 / 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Analytics View The Statistics of Indones. J. Chem.