INVESTIGATION OF THE CONFORMATIONAL INFLUENCES ON THE ESTROGENIC ACTIVITY OF 1,2-BIS(2,6-DICHLORO-4-HYDROXYPHENYL)-ETHYLENEDIAMINES AND OF THEIR PLATINUM(II) COMPLEXES .2. SYNTHESIS AND STUDIES ON THE ESTROGENIC ACTIVITY OF CIS[BIS(2,6-DICHLORO-4-HYDROXYBENZYLAMINE)]DIHALOPLATINUM(II) AND TRANS[BIS(2,6-DICHLORO-4-HYDROXYBENZYLAMINE)]DIHALOPLATINUM(II) COMPLEXES

GUST, R and SCHONENBERGER, H (1994) INVESTIGATION OF THE CONFORMATIONAL INFLUENCES ON THE ESTROGENIC ACTIVITY OF 1,2-BIS(2,6-DICHLORO-4-HYDROXYPHENYL)-ETHYLENEDIAMINES AND OF THEIR PLATINUM(II) COMPLEXES .2. SYNTHESIS AND STUDIES ON THE ESTROGENIC ACTIVITY OF CIS[BIS(2,6-DICHLORO-4-HYDROXYBENZYLAMINE)]DIHALOPLATINUM(II) AND TRANS[BIS(2,6-DICHLORO-4-HYDROXYBENZYLAMINE)]DIHALOPLATINUM(II) COMPLEXES. ARCHIV DER PHARMAZIE, 327 (12). pp. 763-769. ISSN 0365-6233,

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Abstract

2,6-Dichloro-4-hydroxybenzylamine (1) and its N-methyl (2) and N-ethyl (3) derivatives were synthesized and tested for estrogen receptor affinity as well as for estrogenic activity. In contrast to their related highly active 1,2-bis(2,6-dichloro-4-hydroxyphenyl)ethylenediamines (meso-4-meso-6) none of the benzylamines showed hormonal activity. The coordination of the benzylamine 1 to platinum did not lead to an estrogenic compound. The reasons for the different activity of [meso-1,2(bis-2,6-dichloro-4-hydroxyphenyl)ethylenediamine] dichloroplatinum(II) (meso-4-PtCl2) and cis[bis(2,6-dichloro-4-hydroxybenzylamin)]dichloroplatinum(II) (cis-1-PtCl2), the latter of which can be considered as a ring-opened counterpart of the highly active meso-4-PtCl2, are thoroughly discussed under inclusion of conformational facts. The results of this and the preceding work(1)) show, that the pharmacophore meso-1,2-bis(2,6-dichloro-4-hydroxyphenyl)ethylenediamine (meso-4) which is exclusively responsible for the estrogenic activity of meso-4-PtCl4 causes comparable hormonal effects in two different conformations with O-O distances of about 8 Angstrom (complex) and of about 12 Angstrom (diamine). Therefore, we discuss two binding sites for estrogens in their receptor.

Item Type:	Article
Uncontrolled Keywords:	TUMOR-INHIBITING ACTIVITY; ACETOXY-SUBSTITUTED 1,1,2-TRIPHENYLBUT-1-ENES; DEPENDENT MAMMARY-CARCINOMA; ANTI-ESTROGENS; CANCER; RECEPTOR; BREAST; RING; PROPAN-1-AMINE; ANTITUMOR;
Depositing User:	Dr. Gernot Deinzer
Last Modified:	19 Oct 2022 08:39
URI:	https://pred.uni-regensburg.de/id/eprint/52931

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