Abstract
A series of new ethylenediamine (en) platinum(IV) complexes of the type Pt(IV)enX2A2, with X2 = cyclobutane-1,1-dicarboxylato (CBDCA), dichloro or bis(decanoato) and A = acetato, dodecanoato, tetradecanoato, hexadecanoato, octadecanoato, adamantanecarboxylato (Ad) or 3α, 12α-diformoxy-5β-cholato (DFCA) were synthesized and characterized by elemental analysis, infrared and NMR (1H and 13C) spectroscopic techniques. Previous platinum(IV) compounds were usually restricted to trans-dihydroxo or trans-dichloro platinum(IV) complexes. Recently trans-dicarboxylato platinum(IV) complexes with mainly acetate, trifluoracetate or short-chain carboxylate groups (<11 carbons) in the axial position have been described in the literature[1,2,3]. In this paper we report on the synthesis and characterization of a new class of ethylenediamine platinum(IV) compounds that have high lipophilic long-chain carboxylate ligands either in the axial or equatorial position. The platinum(IV) compounds with the lipophilic trans-carboxylate ligands in the axial position were prepared by acylation of the trans-dihydroxo platinum(IV) species using an acyl halide in the presence of pyridine. In contrast to previous publications[1] the yields were excellent (up to 94%!).
Highlights
Introduction cisDiamminedichlomplatinum(ll) is widely used to treat various types of human cancer
In this paper we report on the synthesis and characterization of a new class of ethylenediamine platinum(IV) compounds that have high lipophilic long-chain carboxylate ligands either in the axial or equatorial position
In an attempt to ovemome these limitations, it is desirable to develop new platinum-based anticancer drugs with a broader spectrum of activity, reduced toxicities and an improved clinical effectiveness. Both acceptance and quality of life of cancer patients receiving a platinum-based chemotherapy could be further enhanced by the development of orally administrable platinum complexes
Summary
Silversulfate, hydrogen peroxide and acetic anhydride were pumhased from Merck while ethylenediamine was obtained from Roth, cyclobutane-l,l-dicarboxylic acid from EGA and potassiumtetrachlomplatinate from Degussa. All chemicals obtained from commemial suppliers were used as received. Water was used bidistilled while the required acyl halides were prepared by reaction of the corresponding carboxylic acid with thionyl chloride. Workup was carried out by general methods
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