Tumor inhibiting [1,2-bis(fluorophenylethylenediamine]platinum-(II) complexes. Part I: synthesis

Add time:07/19/2019    Source:sciencedirect.com

The synthesis of the diastereomeric 1,2-bis(2-,3- and 4-fluorophenyl)ethylenediamines 4–6, 10–12 from meso-1,2-bis(2-hydroxyphenyl)ethylenediamine and 2-, 3- and 4-fluorobenzaldehyde by a diaza-Cope-rearrangement and their conversion into the [1,2-bis(2-, 3- and 4-fluorophenyl)ethylenediamine]dihaloplatinum (II) complexes (Hal = Cl, 13–18; Hal = I, 19–24) with K2PtHal4 is described. From the diiodoplatinum(II) complexes (19–24) the better water soluble diaqua[1,2-bis(2-, 3- and 4-fluorophenyl)ethylenediamine]platinum(II) sulfates (25–30) and [1,2-bis(4-fluorophenyl)ethylenediamine]dinitratoplatinum (II) complexes (31 and 32) are obtained by reacting with Ag2SO4 or AgNO3. On the P388D1 leukemia cell line the racemic platinum (II) complexes are more active than their meso-analogues and equiactive with cis-platin. The position of the fluorine atom and the kind of the leaving group do not influence the activity.

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