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| Dokumentenart: | Artikel | ||||
|---|---|---|---|---|---|
| Titel eines Journals oder einer Zeitschrift: | Journal of medicinal chemistry | ||||
| Verlag: | American Chemical Society | ||||
| Band: | 29 | ||||
| Nummer des Zeitschriftenheftes oder des Kapitels: | 3 | ||||
| Seitenbereich: | S. 322-328 | ||||
| Datum: | 1986 | ||||
| Zusätzliche Informationen (Öffentlich): | CAN 104:109110 25-3 Benzene, Its Derivatives, and Condensed Benzenoid Compounds 2962-14-3; 74944-95-9; 78682-42-5 Role: BAC (Biological activity or effector, except adverse), BSU (Biological study, unclassified), BIOL (Biological study) (estrogenic and antitumor activity of); 28714-18-3P; 99749-11-8P; 99749-13-0P; 99749-14-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and demethylation of); 28714-19-4P; 99749-15-2P; 99749-16-3P; 99749-17-4P Role: BAC (Biological activity or effector, except adverse), BSU (Biological study, unclassified), SPN (Synthetic preparation), BIOL (Biological study), PREP (Preparation) (prepn. and estrogenic and antitumor activity of); 28714-28-5P; 99749-12-9P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and hydrogenation of); 711-38-6P; 30724-22-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and reductive coupling of); 76-05-1 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with (methoxyphenyl)magnesium bromides); 13139-86-1; 36282-40-3 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with trifluoroacetic acid) | ||||
| Institutionen: | Chemie und Pharmazie > Institut für Pharmazie > Entpflichtete oder im Ruhestand befindliche Professoren > Prof. Schönenberger | ||||
| Sonstige Projekte: | SFB 234 | ||||
| Identifikationsnummer: |
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| Stichwörter / Keywords: | Neoplasm inhibitors (hexafluorobis(hydroxyphenyl)butanes and -butenes, for mammary tumors) Estrogens Role: RCT (Reactant), RACT (Reactant or reagent) (receptor for, of mammary tumors, inhibition by hexafluorobis(hydroxyphenyl)butanes and -butenes) fluorinated bishydroxyphenylbutane antitumor hexafluorobishydroxyphenylbutane bishydroxyphenylbutane estrogenic hexafluorobishydroxyphenylbutane bishydroxyphenylbutane phenol hexafluorobutanediyl prepn antitumor | ||||
| Dewey-Dezimal-Klassifikation: | 500 Naturwissenschaften und Mathematik > 540 Chemie | ||||
| Status: | Veröffentlicht | ||||
| Begutachtet: | Ja, diese Version wurde begutachtet | ||||
| An der Universität Regensburg entstanden: | Ja | ||||
| Dokumenten-ID: | 17658 |
Zusammenfassung
trans-Bis(trifluoromethyl)ethenes I (R = 3-HO, 4-HO) were prepd. by reductive coupling (TiCl4/Zn/pyridine) of the methoxy-substituted alpha ,alpha ,alpha -trifluoroacetophenones, sepn. of the resulting cis- and trans-stilbene derivs., and ether cleavage with BBr3. The cis-stilbenes were catalytically hydrogenated to give meso-hexafluoro-2,3-bis(hydroxyphenyl)butanes II (R = 3-HO, 4-HO). I and II ...
Zusammenfassung
trans-Bis(trifluoromethyl)ethenes I (R = 3-HO, 4-HO) were prepd. by reductive coupling (TiCl4/Zn/pyridine) of the methoxy-substituted alpha ,alpha ,alpha -trifluoroacetophenones, sepn. of the resulting cis- and trans-stilbene derivs., and ether cleavage with BBr3. The cis-stilbenes were catalytically hydrogenated to give meso-hexafluoro-2,3-bis(hydroxyphenyl)butanes II (R = 3-HO, 4-HO). I and II showed 2- to 10-fold increased binding affinities for the estradiol receptor and enhanced estrogenicity in the uterine wt. test of the immature mouse compared to their unfluorinated analogs. II (R = 3-HO) exhibited a 46% inhibition of the estrone-stimulated uterine growth. All compds. showed tumor growth inhibitory activity corresponding to their RBA values. II (R = 3-HO) gave significant inhibition of the tumor growth on the DMBA-induced hormone-dependent mammary carcinoma of the Sprague-Dawley rat.
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