Synthesis and Antitumor Activity of Enantiomerically Pure [1, 2‐Diamino‐1‐(4‐fluorophenyl) propane]dichloroplatinum(II) Complexes

doi:10.1002/1521-4184(200205)335:5<229::AID-ARDP229>3.0.CO;2-Q

Paper

Synthesis and Antitumor Activity of Enantiomerically Pure [1, 2‐Diamino‐1‐(4‐fluorophenyl) propane]dichloroplatinum(II) Complexes

Published May 1, 2002 · F. Dufrasne, M. Gelbcke, B. Schnurr

Archiv der Pharmazie

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16

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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.

In Vitro Study

Study Snapshot

Enantiomerically pure [1, 2diamino-1(4-fluorophenyl) propane]dichloroplatinum(II) complexes show strong antitumor activity against MCF-7 breast cancer cells, with (SS) and (RR) showing the

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

Synthesis and Antitumor Activity of Enantiomerically Pure [1, 2‐Diamino‐1‐(4‐fluorophenyl) propane]dichloroplatinum(II) Complexes

References

Citations

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