Synthesis of a New DPTYEAP Ligand and Its Complexes with Their Assessments on Physical Properties, Antioxidant, and Biological Potential to Treat Breast Cancer
Abbas Fadhil Yasir(1*), Hayder Obaid Jamel(2)
(1) Department of Chemistry, College of Education, University of Al-Qadisiyah, 58001 Al-Diwaniyah, Iraq
(2) Department of Chemistry, College of Education, University of Al-Qadisiyah, 58001 Al-Diwaniyah, Iraq
(*) Corresponding Author
Abstract
A new series of complexes of the 2-((1E,2E)-1,2-diphenyl-2-(thiazol-2-ylimino)ethylidene)amino)phenol (DPTYEAP) has been synthesized by the reaction of the ligand with metal chlorides of Ni(II), Cu(II), Pt(IV), and AgNO3 in ethanol as a solvent. The ligand was prepared for the two steps. In the first step, compound (A) was synthesized by reacting 2-aminothiazol with benzil in ethanol. Another step is the preparation of the ligand from the reaction of compound (A) with 2-aminophenol. The structures of the ligand and its complexes were confirmed by FTIR, 1H-13C-NMR, UV-Vis spectra, melting points, molar conductivity (C, H, and N), and magnetic susceptibility. The synthesized complexes were prepared in a 1:2 ratio for Ni(II), Cu(II), and Pt(IV) complexes and a 1:1 ratio (M:L) for Ag(I) complexes. The geometric shape of all complexes is octahedral, except for the Ag(I) complex, which is tetrahedral. The antioxidant test for the prepared compounds was carried out. The anticancer test was conducted for each of the ligands and the platinum(IV) complex, and it was found that the platinum complex is more effective against breast cancer cells (MCF-7); thus, it can be used as a potential drug after studying it well.
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References
[1] Miller, M.M., Vasiliadis, T., Rochman, C.M., Repich, K., Patrie, J.T., Anderson, R.T., and Harvey, J.A., 2023, Factors associated with perceived personal risk for breast cancer among women with dense breasts, Clin. Imaging, 93, 34–38.
[2] Mathelin, C., Domínguez-Gil, B., Özmen, V., and Lodi, M., 2023, European guidelines concerning the transplantation of organs from donors with a history of breast cancer, Eur. J. Breast Health, 19 (1), 106–109.
[3] Karademas, E.C., Roziner, I., Mazzocco, K., Pat-Horenczyk, R., Sousa, B., Oliveira-Maia, A.J., Stamatakos, G., Cardoso, F., Frasquilho, D., Kolokotroni, E., Lemos, R., Marzorati, C., Mattson, J., Pettini, G., Spyropoulou, E., Poikonen-Saksela, P., and Simos, P., 2022, The mutual determination of self-efficacy to cope with cancer and cancer-related coping over time: A prospective study in women with breast cancer, Psychol. Health, 1–14.
[4] Terrisse, S., Derosa, L., Iebba, V., Ghiringhelli, F., Vaz-Luis, I., Kroemer, G., Fidelle, M., Christodoulidis, S., Segata, N., Thomas, A.M., Martin, A.L., Sirven, A., Everhard, S., Aprahamian, F., Nirmalathasan, N., Aarnoutse, R., Smidt, M., Ziemons, J., Caldas, C., Loibl, S., Denkert, C., Durand, S., Iglesias, C., Pietrantonio, F., Routy, B., André, F., Pasolli, E., Delaloge, S., and Zitvogel, L., 2021, Intestinal microbiota influences clinical outcome and side effects of early breast cancer treatment, Cell Death Differ., 28 (9), 2778–2796.
[5] Scarim, C.B., and Chin, C.M., 2022, Recent trends in drug development for the treatment of adenocarcinoma breast cancer: Thiazole, triazole, and thiosemicarbazone analogues as efficient scaffolds, Anti-Cancer Agents Med. Chem., 22 (12), 2204–2240.
[6] Campana, L.G., Galuppo, S., Valpione, S., Brunello, A., Ghiotto, C., Ongaro, A., and Rossi, C.R., 2014, Bleomycin electrochemotherapy in elderly metastatic breast cancer patients: Clinical outcome and management considerations, J. Cancer Res. Clin. Oncol., 140 (9), 1557–1565.
[7] Özbek, O., and Gürdere, M.B., 2021, Synthesis and anticancer properties of 2-aminothiazole derivatives, Phosphorus, Sulfur Silicon Relat. Elem., 196 (5), 444–454.
[8] Alizadeh, S.R., and Hashemi, S.M., 2021, Development and therapeutic potential of 2-aminothiazole derivatives in anticancer drug discovery, Med. Chem. Res., 30 (4), 771–806.
[9] Minickaitė, R., Grybaitė, B., Vaickelionienė, R., Kavaliauskas, P., Petraitis, V., Petraitienė, R., Tumosienė, I., Jonuškienė, I., and Mickevičius, V., 2022, Synthesis of novel aminothiazole derivatives as promising antiviral, antioxidant and antibacterial candidates, Int. J. Mol. Sci., 23 (14), 7688.
[10] Ding, M., Wu, N., Lin, Q., Yan, Y., Yang, Y., Tian, G., An, L., and Bao, X., 2022, Discovery of novel quinazoline-2-aminothiazole hybrids containing a 4-piperidinylamide linker as potential fungicides against the phytopathogenic fungus Rhizoctonia solani, J. Agric. Food Chem., 70 (33), 10100–10110.
[11] Makam, P., and Kannan, T., 2014, 2-Aminothiazole derivatives as antimycobacterial agents: Synthesis, characterization, in vitro and in silico studies, Eur. J. Med. Chem., 87, 643–656.
[12] Farouk Elsadek, M., Mohamed Ahmed, B., and Fawzi Farahat, M., 2021, An overview on synthetic 2-aminothiazole-based compounds associated with four biological activities, Molecules, 26 (5), 1449.
[13] Niu, Z.X., Wang, Y.T., Zhang, S.N., Li, Y., Chen, X.B., Wang, S.Q., and Liu, H.M., 2023, Application and synthesis of thiazole ring in clinically approved drugs, Eur. J. Med. Chem., 250, 115172.
[14] Ates, B., Koytepe, S., Ulu, A., Gurses, C., and Thakur, V.K., 2020, Chemistry, structures, and advanced applications of nanocomposites from biorenewable resources, Chem. Rev., 120 (17), 9304–9362.
[15] Razzaq, A.S., and Nahi, R.J., 2021, In vitro, evaluation of antioxidant and antibacterial activities of new 1,2,3-triazole derivatives containing 1,2,4-triazole ring, Syst. Rev. Pharm., 12 (1), 196–200.
[16] Kyhoiesh, H.A.K., and Al-Adilee, K.J., 2021, Synthesis, spectral characterization, antimicrobial evaluation studies and cytotoxic activity of some transition metal complexes with tridentate (N,N,O) donor azo dye ligand, Results Chem., 3, 100245.
[17] Charisiadis, P., Kontogianni, V.G., Tsiafoulis, C.G., Tzakos, A.G., Siskos, M., and Gerothanassis, I.P., 2014, 1H-NMR as a structural and analytical tool of intra-and intermolecular hydrogen bonds of phenol-containing natural products and model compounds, Molecules, 19 (9), 13643–13682.
[18] Mohammadi, K., and Zahedi, M., 2012, Tridentate Schiff base compounds of 2-aminophenol: Synthesis, characterization and complexation with IIIA elements, Global J. Inorg. Chem., 3 (2), 1–12.
[19] Raman, N., 2002, Synthesis, structural characterization, redox and antimicrobial studies of Schiff base copper(II), nickel(II), cobalt(II), manganese(II), zinc(II) and oxovanadium(II) complexes derived from benzil and 2-aminobenzyl alcohol, Pol. J. Chem., 76 (8), 1085–1094.
[20] Abouzied, A.S., Break, M.K.B., Huwaimel, B., Hussein, W., Alafnan, A., and Younes, K.M., 2023, Discovery of a novel synthetic thiazole-benzimidazole conjugate that acts as a potent pancreatic lipase inhibitor using in silico and in vitro approaches, Indian J. Pharm. Educ. Res., 57 (1), 218–227.
[21] Emadi, A., 2020, Schiff benzimidazole derivatives: synthesis, properties and antimicrobial activity, Int. J. Farming Allied Sci., 9, 72–82.
[22] Çakmak, Ş., Koşar Kırca, B., Veyisoğlu, A., Yakan, H., Ersanlı, C.C., and Kütük, H., 2022, Experimental and theoretical investigations on a furan-2-carboxamide-bearing thiazole: Synthesis, molecular characterization by IR/NMR/XRD, electronic characterization by DFT, Hirshfeld surface analysis and biological activity, Acta Crystallogr., Sect. C: Struct. Chem., 78 (3), 201–211.
[23] More, R.M., Kadam, A.B., Dalvi, S.P., Humne, V.T., and Junne, S.B., 2022, Synthesis, characterization and anti-bacterial activity of Schiff base hybrid from 2-aminothiazole-pyrazolecarboxaldehyde, J. Adv. Chem. Sci., 8 (4), 781–783.
[24] Rathnayaka, C., George, S., Abeysinghe, J.P., Lynch, V.M., and Gross, D.E., 2022, Synthetic, spectroscopic, and computational investigations of readily accessible 2‐phenyl‐3‐alkylbenzoxazaboroles, J. Heterocycl. Chem., 59 (6), 1036–1044.
[25] Zelelew, D., Endale, M., Melaku, Y., Kedir, F., Demissie, T.B., Ombito, J.O., and Eswaramoorthy, R., 2022, Synthesis, anti-bacterial, and antioxidant activities of thiazolyl-pyrazoline Schiff base hybrids: A combined experimental and computational study, J. Chem., 2022, 3717826.
[26] Duc, D.X., and Lanh, H.T., 2022, Microwave-assisted, [Bmim]HSO4-catalyzed synthesis of tetrasubstituted imidazoles via four-component reaction, Vietnam J. Sci. Technol., 60 (3), 383–390.
[27] Al-Jibouri, M.N., Hafidh, F.R., and Rasheed, A.M., 2014, Synthesis and characterization of some transition metal complexes with tridentate N3 donor Schiff base derived from 2-aminothiazole, Eur. Chem. Bull., 3 (6), 559–562.
[28] Camellia, F.K., Ashrafuzzaman, M., Islam, M.N., Banu, L.A., and Zahan, M.K.E., 2022, Isoniazid derived Schiff base metal complexes: Synthesis, characterization, thermal stability, anti-bacterial and antioxidant activity study, Asian J. Chem. Sci., 11 (4), 23–36.
[29] Al-Amery, H., Al-Abdaly, B.I., and Albayaty, M.K., 2016, Synthesis, characterization and anti-bacterial activity of new complexes of some lanthanide ions with 15-crown-5 and 18-crown-6, Orient. J. Chem., 32 (2), 1025–1048.
[30] Abdel-Rahman, L.H., Adam, M.S.S., Al-Zaqri, N., Shehata, M.R., Ahmed, H.E.S., and Mohamed, S.K., 2022, Synthesis, characterization, biological and docking studies of ZrO(II), VO(II) and Zn(II) complexes of a halogenated tetra-dentate Schiff base, Arabian J. Chem., 15 (5), 103737.
[31] Gul, Z., Din, N.U., Khan, E., Ullah, F., and Nawaz Tahir, M., 2020, Synthesis, molecular structure, anti-microbial, antioxidant and enzyme inhibition activities of 2-amino-6-methylbenzothiazole and its Cu(II) and Ag(I) complexes, J. Mol. Struct., 1199, 126956.
[32] Barfeie, H., Grivani, G., Eigner, V., Dusek, M., and Khalaji, A.D., 2018, Copper(II), nickel(II), zinc(II) and vanadium(IV) Schiff base complexes: Synthesis, characterization, crystal structure determination, and thermal studies, Polyhedron, 146, 19–25.
[33] Thakar, A., Joshi, K., Pandya, K., and Pancholi, A., 2011, Coordination modes of a Schiff base derived from substituted 2-aminothiazole with chromium(III), manganese(II), iron(II), cobalt(II), nickel(II) and copper(II) metal ions: Synthesis, spectroscopic and antimicrobial studies, J. Chem., 8, 282061.
[34] Daravath, S., Kumar, M.P., Rambabu, A., Vamsikrishna, N., Ganji, N., and Shivaraj, S., 2017, Design, synthesis, spectral characterization, DNA interaction and biological activity studies of copper(II), cobalt(II) and nickel(II) complexes of 6-amino benzothiazole derivatives, J. Mol. Struct., 1144, 147–158.
[35] Swami, S., Sharma, N., Agarwala, A., Shrivastava, V., and Shrivastava, R., 2021, Schiff base anchored silver nanomaterial: An efficient and selective nano probe for fluoride detection in an aqueous medium, Mater. Today: Proc., 43, 2926–2932.
[36] Adnan, S., Al-Adilee, K.J., and Abedalrazaq, K.A., 2020, Synthesis, spectral characterization and anticancer studies of novel azo Schiff base and its complexes with Ag(I), Au(III) and Pt(IV) ions, Egypt. J. Chem., 63 (12), 4749–4756.
[37] Elkanzi, N.A., Hrichi, H., Salah, H., Albqmi, M., Ali, A.M., and Abdou, A., 2023, Synthesis, physicochemical properties, biological, molecular docking and DFT investigation of Fe(III), Co(II), Ni(II), Cu(II) and Zn(II) complexes of the 4-[(5-oxo-4,5-dihydro-1,3-thiazol-2-yl)hydrazono]methyl}phenyl 4-methylbenzenesulfonate Schiff-base ligand, Polyhedron, 230, 116219.
[38] Rajmane, S., Ubale, V.P., Dama, L.B., Asabe, M.R., and More, P.G., 2013, Synthesis, spectral and biological studies of thiazole Schiff base derived from 4-(2’-fluorophenyl)-2-aminothiazole, Int. J. Pharm. Sci. Invent., 2 (7), 33–36.
DOI: https://doi.org/10.22146/ijc.81734
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