Design, synthesis, characterisation and chemical reactivity of mixed-ligand platinum(II) oxadiazoline complexes with potential cytotoxic properties

Dalton Transactions : an International Journal of Inorganic Chemistry
Gabriele WagnerJames Sayer

Abstract

A series of mixed ligand platinum(II) oxadiazoline complexes bearing 7-nitro-1,3,5-triazaadamantane (7-NO(2)TAA) as a labile and reactive nitrogen ligand has been synthesised from easily accessible starting materials. [2+3] cycloaddition of nitrones R(1)R(2)C-N(+)(Me)O(-) to only one of the nitrile ligands in trans-[PtX(2)(PhCN)(2)] (X = Cl, Br) results in the selective formation of mono-oxadiazoline complexes trans-[PtX(2)(PhCN){N=C(Ph)-O-N(Me)-CR(1)R(2)}] from which the remaining nitrile can be replaced by 7-NO(2)TAA. The resulting complexes trans-[PtX(2)(7-NO(2)TAA) {N=C(Ph)-O-N(Me)-CR(1)R(2)}] and their precursors were characterised by elemental analysis, IR and multinuclear NMR spectroscopy.The suitability of the target complexes as anticancer agents was extrapolated from their general chemical reactivity. They are stable in DMSO, but react with thiols and undergo aquation of a chloro ligand. In the absence of a competing ligand, the coordinated 7-NO(2)TAA ligand slowly hydrolyses in an aqueous medium under release of formaldehyde, and this could induce bioactivity independent of the one typically found with platinum compounds. With nitrogen heterocycles such as pyridine a slow exchange of the 7-NO(2)TAA ligand occurs. A c...Continue Reading

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Citations

Mar 6, 2015·Chemical Reviews·Vadim P BoyarskiyVadim Yu Kukushkin
Sep 7, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Stefanie SiesteGabriele Wagner
Dec 5, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Helgi Freyr Jónsson, Anne Fiksdahl
Oct 11, 2013·Acta Crystallographica. Section E, Structure Reports Online·Andreii S KritchenkovValentina A Kalibabchuk
Mar 11, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Andreii S KritchenkovVadim Yu Kukushkin

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