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

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.

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 Creators:
Pollak, David1, Author           
Goddard, Richard2, Author           
Pörschke, Klaus-Richard3, Author           
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              
2Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445625              
3Research Group Pörschke, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445616              

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 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.

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Language(s): eng - English
 Dates: 2016-07-142016-09-19
 Publication Status: Issued
 Pages: 12
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/acs.inorgchem.6b01690
 Degree: -

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Title: Inorganic Chemistry
  Abbreviation : Inorg. Chem.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 55 (18) Sequence Number: - Start / End Page: 9424 - 9435 Identifier: ISSN: 0020-1669
CoNE: https://pure.mpg.de/cone/journals/resource/0020-1669