Synthesis and P-388 Antitumor Properties of the Four Diastereomeric l-Hydroxy-3,4-diaminocyclohexane-Cl2PtII Complexes

Donald T. Witiak, David P. Rotella, Yong Wei, Joyce A. Filppi, Judith C. Gallucci

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Synthesis and antileukemic activity in vivo of the four diastereomeric l-hydroxy-354-diaminocyclohexane-Cl2PtII complexes (Cl2PtII-3a-d) are described. Respective bis(phenylmethyl) (lα,2α,4β)-, (lα,2α,4α)-, (lα,2β,4β)-, and (lα, 2β 4α)- (4-hydroxy- 1,2-cyclohexanediyl) bis (carbamates) (5a, 5b, 7a, 7b) were prepared by hydroboration-oxidation of the bis(carbobenzoxyamino) derivatives (4, 5) of cis- and trans-4,5-diaminocyclohexene. The relative stereochemistry of intermediates 5a and 5b was established by correlation with the alcohol obtained by NaBH4reduction of bis(phenylmethyl) (lα,2α,3α,4α)-(3,4-epoxy-l,2-cyclohexanediyl)bis(carbamate) (8), the all-cis stereochemistry of which was unambiguously determined by X-ray crystallographic analysis. In the P-388 murine leukemia model these monohydroxycyclohexanediamine-Pt11 complexes were more effective than the Pt11 complexes of the related diol diamines la-e but were less active than the cisplatin positive control.

Original languageEnglish
Pages (from-to)214-217
Number of pages4
JournalJournal of Medicinal Chemistry
Issue number1
StatePublished - 1 Jan 1989


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