PMID: 11382148May 31, 2001Paper

1-(2,6-dichloro-4-hydroxyphenyl)-2-phenylethanes--new biological response modifiers for the therapy of breast cancer. Synthesis and evaluation of estrogenic/antiestrogenic properties

Archiv der Pharmazie
Sabine SchertlHelmut Schönenberger

Abstract

[meso-1,2-Bis(2,6-dichloro-4-hydroxyphenyl)ethylenediamine]platinum(II) complexes (meso-1-PtLL'; L,L' = Cl or L = H2O and L' = OSO3) are highly effective towards hormone-sensitive, rodent breast cancers due to their significant estrogenic potencies. Their antitumor activities are caused by modification of the immune response. The pharmacophor of these compounds, the 1,2-bis(2,6-dichloro-4-hydroxyphenyl)ethane (23H), was used as the lead structure in a structure-activity study with the goal of finding new biological response modifiers for the therapy of breast cancer. As intermediates for the synthesis of the 23H derivatives, the CH3O-substituted stilbenes 12E/12Z-16E/16Z were prepared by reaction of the related benzyltriphenylphosphonium halides with 2,6-dichloro-4-methoxybenzaldehyde by the method of Wittig/Campbell and Donald, respectively. Separation of the E/Z-mixtures was performed by fractional crystallization and/or column chromatography. The E-1,2-bis(2,6-dichloro-4-methoxyphenyl)ethene (17E) was obtained by reductive coupling of 2,6-dichloro-4-methoxybenzaldehyde with TiCl4/Zn according to the method of Mukaiyama. Illumination of the solution of 17E in benzene with UV light resulted in an E/Z-isomerization. Compound 17...Continue Reading

References

Jan 1, 1986·Journal of Cancer Research and Clinical Oncology·M R Schneider
Dec 1, 1985·Journal of Medicinal Chemistry·M R SchneiderH Schönenberger
Jan 1, 1967·Tetrahedron·H Güsten, M Salzwedel

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