F. Dufrasne, M. Gelbcke, B. Schnurr
May 1, 2002
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0
Influential Citations
16
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Quality indicators
Journal
Archiv der Pharmazie
Abstract
Enantiomerically pure 1, 2‐diamino‐1‐(4‐fluorophenyl)propanes were synthesized by stereospecific and stereoselective procedures by use of the (1R, 2S)‐ and (1S, 2R)‐2‐amino‐1‐(4‐fluorophenyl)propanols (12a) as intermediates. The enantiomeric purity was determined by 1H NMR spectroscopy after conversion of the propanolamines and the diamines with (1R)‐myrtenal into mono‐ and diimines. For the coordination to platinum the diamines were reacted with K2PtCl4. The resulting dichloroplatinum(II) complexes 4F‐Ph/Me‐PtCl2 were tested for antiproliferative activity on the MCF‐7 breast cancer cell line. (SS)‐ and (RR)‐4F‐Ph/Me‐PtCl2 produced the strongest inhibitory effect. Both complexes showed cytocidal effects, (SS)‐4F‐Ph/Me‐PtCl2 even in a concentration of 1 μM. The (1S, 2R)‐ and (1R, 2S)‐configurated complexes were far less active (SS > RR > RS = SR) and comparable in this respect with the standard cisplatin.