Cyclopalladated complexes containing tridentate thiosemicarbazone ligands of biological significance: Synthesis, structure and antimalarial activity


Chellan, P; Nasser, S; Vivas, L; Chibale, K; Smith, GS; (2010) Cyclopalladated complexes containing tridentate thiosemicarbazone ligands of biological significance: Synthesis, structure and antimalarial activity. Journal of organometallic chemistry, 695 (19-20). pp. 2225-2232. ISSN 0022-328X DOI: https://doi.org/10.1016/j.jorganchem.2010.06.010

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Abstract

The C-H activation reaction of two aryl-derived thiosemicarbazones with K-2[PdCl4] affords tetranuclear cyclopalladated complexes (3 and 4) where the thiosemicarbazone ligand acts as a tridentate donor [C,N,S] coordinated to palladium via the ortho-carbon of the aryl ring, imine nitrogen and thiolato sulfur. The palladiumesulfur bridging coordination bonds give rise to a Pd4S4 core. These Pd-S-bridging bonds were cleaved with a variety of mono-and bis-phosphines to give a series of mono, di and tetranuclear organopalladium complexes (5-12) where the phosphorus atom coordinates to palladium trans to the imine nitrogen. All of the complexes were fully characterized using various analytical and spectroscopic techniques. These palladium complexes along with their free ligands were evaluated as bioorganometallic antimalarial agents against two Plasmodium falciparum strains, 3D7 (chloroquine sensitive) and K1 (chloroquine and pyrimethamine resistant). Some of the complexes were found to be moderate inhibitors of parasite growth and were more active than the corresponding free ligand. (C) 2010 Elsevier B. V. All rights reserved.

Item Type: Article
Keywords: Bioorganometallic chemistry, Palladium, Cyclopalladation, Thiosemicarbazone, Antimalarial activity, P-ISOPROPYLBENZALDEHYDE THIOSEMICARBAZONE, CYCLOMETALATED PALLADIUM(II), COMPOUNDS, POTENTIAL ANTITUMOR AGENTS, ANTI-MALARIAL AGENTS, TUMOR-CELL, LINES, PLASMODIUM-FALCIPARUM, 2-ACETYLPYRIDINE THIOSEMICARBAZONES, MOLECULAR-STRUCTURE, CYSTEINE PROTEASE, SALICYLALDEHYDE, THIOSEMICARBAZONE
Faculty and Department: Faculty of Infectious and Tropical Diseases > Dept of Immunology and Infection
Research Centre: Malaria Centre
Web of Science ID: 280847000010
URI: http://researchonline.lshtm.ac.uk/id/eprint/3060

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