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| Item type: | Article | ||||
|---|---|---|---|---|---|
| Journal or Publication Title: | Archiv der Pharmazie | ||||
| Publisher: | John Wiley & Sons | ||||
| Volume: | 327 | ||||
| Number of Issue or Book Chapter: | 12 | ||||
| Page Range: | pp. 763-769 | ||||
| Date: | 1994 | ||||
| Additional Information (public): | CAN 122:95262 78-7 Inorganic Chemicals and Reactions 82772-93-8 (2,6-Dichloro-4-methoxybenzaldehyde) Role: RCT (Reactant), RACT (Reactant or reagent) (for prepn. of (dichlorohydroxybenzyl)amine and its platinum complexes); 10025-99-7P (Dipotassium tetrachloroplatinate(2-); 14708-56-6P (Dipotassium tetraiodoplatinate(2-); 82772-94-9P; 82772-95-0P; 160522-39-4P (2,6-Dichloro-4-methoxybenzaldoxime); 160522-40-7P (2,6-Dichloro-4-methoxybenzylamine); 160522-41-8P ((2,6-Dichloro-4-methoxybenzyl)methylamine); 160522-42-9P ((2,6-Dichloro-4-methoxybenzyl)ethylamine) Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (for prepn. of (dichlorohydroxybenzyl)amine and its platinum complexes); 160522-33-8P (2,6-Dichloro-4-hydroxybenzylamine); 160522-34-9P ((2,6-Dichloro-4-hydroxybenzyl)methylamine); 160522-35-0P ((2,6-Dichloro-4-hydroxybenzyl)ethylamine) Role: BAC (Biological activity or effector, except adverse), BSU (Biological study, unclassified), RCT (Reactant), SPN (Synthetic preparation), BIOL (Biological study), PREP (Preparation), RACT (Reactant or reagent) (prepn. and estrogenic activity of (dichlorohydroxybenzyl)amine and its platinum complexes); 160522-36-1P (cis-Dichlorobis(2,6-dichloro-4-methoxybenzylamine)platinum); 160522-37-2P (cis-Dichlorobis(2,6-dichloro-4-hydroxybenzylamine)platinum); 160522-38-3P (trans-Bis(2,6-dichloro-4-hydroxybenzylamine)diiodoplatinum) Role: BAC (Biological activity or effector, except adverse), BSU (Biological study, unclassified), SPN (Synthetic preparation), BIOL (Biological study), PREP (Preparation) (prepn. and estrogenic activity of (dichlorohydroxybenzyl)amine and its platinum complexes) | ||||
| Institutions: | Chemistry and Pharmacy > Institute of Pharmacy > Alumni or Retired Professors > Prof. Schönenberger | ||||
| Projects: | SFB 234 | ||||
| Identification Number: |
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| Keywords: | Estrogens Role: BAC (Biological activity or effector, except adverse), BSU (Biological study, unclassified), SPN (Synthetic preparation), BIOL (Biological study), PREP (Preparation) (prepn. and estrogenic activity of (dichlorohydroxybenzyl)amine and its Estrogen receptors Role: PRP (Properties) (prepn. and estrogenic activity of (dichlorohydroxybenzyl)amine and its platinum complexes) Receptors Role: PRP (Properties) (estrogen, prepn. and estrogenic activity of (dichlorohydroxybenzyl)amine and its platinum complexes) estrogen activity dichlorohydroxybenzylamine platinum complex | ||||
| Dewey Decimal Classification: | 500 Science > 540 Chemistry & allied sciences | ||||
| Status: | Published | ||||
| Refereed: | Yes, this version has been refereed | ||||
| Created at the University of Regensburg: | Yes | ||||
| Item ID: | 17704 |
Abstract
2,6-Dichloro-4-hydroxybenzylamine (1) and its N-Me (2) and N-Et (3) derivs. 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 ...
Abstract
2,6-Dichloro-4-hydroxybenzylamine (1) and its N-Me (2) and N-Et (3) derivs. 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 compd. 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-hydroxybenzylamine)]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 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-PtCl2 causes comparable hormonal effects in two different conformations with O-O distances of .apprx.8 .ANG. (complex) and of .apprx.12 .ANG. (diamine). Therefore, two binding sites for estrogens in their receptor are discussed.
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