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Synthesis and Structures of 9‑Oxabispidine Analogues of Cisplatin, Carboplatin, and Oxaliplatin

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Pollak,  David
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Goddard,  Richard
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Pörschke,  Klaus-Richard
Research Group Pörschke, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Pollak, D., Goddard, R., & Pörschke, K.-R. (2016). Synthesis and Structures of 9‑Oxabispidine Analogues of Cisplatin, Carboplatin, and Oxaliplatin. Inorganic Chemistry, 55(18), 9424-9435. doi:10.1021/acs.inorgchem.6b01690.


Cite as: http://hdl.handle.net/11858/00-001M-0000-002C-1973-E
Abstract
The literature synthesis of 9-oxabispidine [OC6H10(NH)2, C] has been revisited and optimized, which includes determination of the crystal structures of C, the secondary component trans-(PhSO2)NC4H6O(CH2I)2 (trans-III), and the unexpected solute intermediate OC6H10(NSO2Ph)2· 1 /2py (V· 1 /2py). The reaction of (1,5-hexadiene)platinum dichloride with C yields {OC6H10(NH)2}PtCl2 (C1), which is converted to {OC6H10(NH)2}- Pt(cbdca)·5H2O (C2) and {OC6H10(NH)2}Pt(C2O4) (C3). In the crystal, C1 forms a planar 2D network by N−H··Cl and N−H··O hydrogen bonding. In the crystal structure of C2, which is isomorphous to the parent bispidine compound (A2), all complex molecules are encapsulated by a water shell. While complexes C1 and C3 are virtually insoluble in water, C2 dissolves quite well. The low cytotoxicity of compounds C1−C3 is explained by an increased polarity of the bonds in the C skeleton as a consequence of the electronegative O atom.