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NOVEL PALLADIUM(II) COMPLEXES OF PYRAZOLE-CONTAINING SCHIFF BASE LIGANDS: SYNTHESIS, STRUCTURAL CHARACTERIZATION, AND CYTOTOXICITY OF THE PALLADIUM(II) COMPLEXES OF 2-{1-[2-(1,3-DIMETHYL-4-NITRO-1H-PYRAZOL-5-YL) HYDRAZONO]ETHYL} PYRIDINE (APHP) AND ITS ANALOGUE 2-{1-[2-(1,3-DIMETHYL-4-NITRO- 1H-PYRAZOL-5-YL)HYDRAZONO]METHYL} PYRIDINE (PCHP)

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Abstract

Treatment of [Pd(PhCN)2Cl2] with one equivalent of 2-{1-[2-(1,3-dimethyl-4-nitro-1H-pyrazol-5-yl)hydrazono]methyl} pyridine (PCHP) (3a) or its analogue 2-{1-[2-(1,3-dimethyl-4-nitro-1H-pyrazol-5-yl)hydrazono]ethyl} pyridine (APHP) (3b) produce corresponding pyridine-hydrazone Schiff base coordination complexes [Pd(PCHP)Cl2] (4a) and [Pd(APHP)Cl2] (4b), respectively. Compounds 4a,b are characterized by elemental analysis, IR spectroscopy, and 1H NMR. Attempts to crystalize 4b lead to N–C(sp3)–E pincer palladacycle [Pd(APHP–H)Cl(DMSO)] (5). The molecular structures of 5 in the solid state are determined by single crystal X-ray structure analysis. The X-ray crystal structure of 5 shows the existence of the five-membered metallacycle through the coordination of \(\text{N}-\text{CH}_{2}^{-}\) and pyridine N to the palladium center and the cis arrangement between the metalated nitrogen atom and DMSO. The cytotoxicity of the two ligands and palladium(II) complexes 4a and 5 evaluated against K562 human cancer cell line. The corresponding GI50 (50% growth inhibition) values are compared to the cytotoxicity of cisplatin, under the same experimental conditions, and the results indicate inactive ligands and a superior activity to cisplatin for the complexes.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Hashemite University, Hashemite Kingdom of Jordan

    A. S. Abushamleh, K. A. Abu-Safieh & N. J. Alwahsh

  2. Department of Chemistry, Faculty of Sciences, University of Sharjah, Sharjah, UAE

    M. A. Khanfar

  3. Department of Chemistry, University of Jordan, Amman, Hashemite Kingdom of Jordan

    D. Taher

  4. Department of Biology and Biotechnology, Hashemite University, Zarqa, Hashemite Kingdom of Jordan

    L. Tahtamouni

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  1. A. S. Abushamleh
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Text © The Author(s), 2021, published in Zhurnal Strukturnoi Khimii, 2021, Vol. 62, No. 7, pp. 1189-1199.https://doi.org/10.26902/JSC_id74465

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Abushamleh, A.S., Abu-Safieh, K.A., Khanfar, M.A. et al. NOVEL PALLADIUM(II) COMPLEXES OF PYRAZOLE-CONTAINING SCHIFF BASE LIGANDS: SYNTHESIS, STRUCTURAL CHARACTERIZATION, AND CYTOTOXICITY OF THE PALLADIUM(II) COMPLEXES OF 2-{1-[2-(1,3-DIMETHYL-4-NITRO-1H-PYRAZOL-5-YL) HYDRAZONO]ETHYL} PYRIDINE (APHP) AND ITS ANALOGUE 2-{1-[2-(1,3-DIMETHYL-4-NITRO- 1H-PYRAZOL-5-YL)HYDRAZONO]METHYL} PYRIDINE (PCHP). J Struct Chem 62, 1112–1122 (2021). https://doi.org/10.1134/S0022476621070167

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