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Synthesis and Antitumor Activity of Enantiomerically Pure [1, 2‐Diamino‐1‐(4‐fluorophenyl) propane]dichloroplatinum(II) Complexes
Author(s) -
Dufrasne Francois,
Gelbcke Michael,
Schnurr Beate,
Gust Ronald
Publication year - 2002
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/1521-4184(200205)335:5<229::aid-ardp229>3.0.co;2-q
Subject(s) - chemistry , enantiomer , stereoselectivity , stereochemistry , stereospecificity , nuclear magnetic resonance spectroscopy , diamine , diastereomer , medicinal chemistry , organic chemistry , catalysis
Enantiomerically pure 1, 2‐diamino‐1‐(4‐fluorophenyl)propanes were synthesized by stereospecific and stereoselective procedures by use of the (1 R , 2 S )‐ and (1 S , 2 R )‐2‐amino‐1‐(4‐fluorophenyl)propanols ( 12a ) as intermediates. The enantiomeric purity was determined by 1 H NMR spectroscopy after conversion of the propanolamines and the diamines with (1 R )‐myrtenal into mono‐ and diimines. For the coordination to platinum the diamines were reacted with K 2 PtCl 4 . The resulting dichloroplatinum(II) complexes 4F‐Ph/Me‐PtCl 2 were tested for antiproliferative activity on the MCF‐7 breast cancer cell line. ( SS )‐ and ( RR )‐ 4F‐Ph/Me‐PtCl 2 produced the strongest inhibitory effect. Both complexes showed cytocidal effects, ( SS )‐ 4F‐Ph/Me‐PtCl 2 even in a concentration of 1 μM. The (1 S , 2 R )‐ and (1 R , 2 S )‐configurated complexes were far less active ( SS > RR > RS = SR ) and comparable in this respect with the standard cisplatin.