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Review
. 2014 Apr 23;114(8):4470-95.
doi: 10.1021/cr4004314. Epub 2013 Nov 27.

Synthetic methods for the preparation of platinum anticancer complexes

Justin J Wilson  1 , Stephen J Lippard
Affiliations
Review

Synthetic methods for the preparation of platinum anticancer complexes

Justin J Wilson et al. Chem Rev. .
No abstract available

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Figures

Chart 1
Chart 1
Chemical structures of the clinically used platinum-based anticancer drugs. The top three complexes, cisplatin, carboplatin, and oxaliplatin, are approved for use worldwide. The bottom three complexes, nedaplatin, lobaplatin, and heptaplatin, are approved for use in Japan, China, and Korea, respectively.
Chart 2
Chart 2
Structures of mixed amine platinum(II) complexes that have undergone clinical trials.
Chart 3
Chart 3
Examples of cationic monofunctional platinum(II) complexes that exhibit anticancer activity.–
Chart 4
Chart 4
Depiction of the six different stereoisomers of [PtCl2(iminoether)2]. The terms cis and trans refer to the stereochemistry at the platinum(II) center, whereas E and Z denote the stereochemistry at the C–N double bond of the iminoether ligands.
Chart 5
Chart 5
Examples of several clinically investigated platinum(IV) anticancer agents.
Figure 1
Figure 1
Different components of platinum anticancer agents. Additional factors that can be varied are the stereochemistry and the respective number of non-leaving and leaving group ligands.
Scheme 1
Scheme 1
Synthesis of cisplatin using the method of Dhara. All reactions steps are carried out in aqueous solution.
Scheme 2
Scheme 2
The use of the Kurnakow test to distinguish cis- and trans-[Pt(NH3)2Cl2]. Reactions with thiourea are carried out in sub-boiling water.
Scheme 3
Scheme 3
Synthesis of trans-[Pt(NH3)2Cl2]. Reactions are carried out in water at elevated (50–100 °C) temperatures.
Scheme 4
Scheme 4
Different synthetic routes to replace halide leaving group ligands.,
Scheme 5
Scheme 5
Synthesis of cis-[Pt(NH3)LCl2] starting from cisplatin using the [Pt(NH3)Cl3]− ion as an intermediate.,
Scheme 6
Scheme 6
Synthesis of mixed amine complexes, cis-[PtLL'I2], via iodido-bridged dimer intermediates.,
Scheme 7
Scheme 7
Synthesis of mixed amine complexes with a chelating oxygen donor leaving group.
Scheme 8
Scheme 8
Synthesis of trans-[PtLL'Cl2].
Scheme 9
Scheme 9
Synthesis of [Pt(NH33Cl]Cl.
Scheme 10
Scheme 10
Two different synthetic routes for the preparation of cis-[Pt(L2)(RR'SO)Cl]Cl.
Scheme 11
Scheme 11
Synthesis of cis-[Pt(NH3)2LCl]NO3.,
Scheme 12
Scheme 12
Synthesis of monofunctional, thiourea platinum(II) complexes.
Scheme 13
Scheme 13
Synthesis of cis- (top), trans-[PtCl2(iminoether)2] (middle), and trans-[PtCl2(imino thioether)2].,,
Scheme 14
Scheme 14
Synthesis of cis- (top) and trans-[PtCl2(amidine)2] (middle). Room temperature conditions and extended reactions times lead to the formation of primarily trans-[Pt(NH2R')2(amidine)2] from trans-[PtCl2(NCR)2] (bottom).
Scheme 15
Scheme 15
Multi-step synthetic scheme for the preparation of monofunctional platinum-amidine complexes.
Scheme 16
Scheme 16
Condensation reactions involving the coordinated ammine ligands of cis- and trans-[Pt(NH3)2Cl2], as well as their diiodido analogues.,
Scheme 17
Scheme 17
Outer-sphere ligand-based reactivity pathways of several platinum(II) complexes.–
Scheme 18
Scheme 18
Oxidation of a platinum(II) complex with chlorine (top) and hydrogen peroxide (bottom). The products obtained for the hydrogen peroxide-oxidation are dependent on the solvent used.,
Scheme 19
Scheme 19
Peroxide oxidations of platinum(II) complexes in various acidic solvents.,,,
Scheme 20
Scheme 20
Ring-closing oxidation reactions of [Pt(edma)Cl2] (top), [Pt(edda)Cl2] (middle),, and [Pt(edta)Cl2] (bottom).
Scheme 21
Scheme 21
Preparation of platinum(IV) complexes using different oxidizing agents.–,,–
Scheme 22
Scheme 22
Oxidation of platinum(II) complexes with hypervalent iodine reagents.,
Scheme 23
Scheme 23
Synthetic methods for the preparation of platinum(IV) carboxylates.,,,,
Scheme 24
Scheme 24
Synthesis of mixed trans hydroxo-carboxylato platinum(IV) complexes.,,,
Scheme 25
Scheme 25
Reactivity of platinum(IV) hydroxides with electrophiles.,,
Scheme 26
Scheme 26
Outer-sphere reactivity of platinum(IV) complexes with organic functional groups.,,,–
Scheme 27
Scheme 27
Ligand substitution reactions facilitated by acidic conditions.,,
Scheme 28
Scheme 28
Ligand substitution reactions facilitated by basic conditions, presumably through a base hydrolysis mechanism.,
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References

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