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| Dokumentenart: | Artikel | ||||
|---|---|---|---|---|---|
| Titel eines Journals oder einer Zeitschrift: | Journal of medicinal chemistry | ||||
| Verlag: | American Chemical Society | ||||
| Band: | 28 | ||||
| Nummer des Zeitschriftenheftes oder des Kapitels: | 12 | ||||
| Seitenbereich: | S. 1880-1885 | ||||
| Datum: | 1985 | ||||
| Zusätzliche Informationen (Öffentlich): | CAN 103:195868 25-10 Benzene, Its Derivatives, and Condensed Benzenoid Compounds 2398-37-0 Role: RCT (Reactant), RACT (Reactant or reagent) (Grignard reaction of, with deoxybenzoin deriv.); 75-03-6 Role: RCT (Reactant), RACT (Reactant or reagent) (alkylation by, of deoxybenzoin deriv.); 1023-17-2 Role: RCT (Reactant), RACT (Reactant or reagent) (alkylation of, by Et iodide); 13732-58-6; 98540-35-3; 98540-36-4; 98540-37-5 Role: RCT (Reactant), RACT (Reactant or reagent) (hydrolysis of, and O-acetylation of product from); 78423-10-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and Grignard reaction of, with bromoanisole); 98540-29-5P; 98540-30-8P; 98540-33-1P Role: BAC (Biological activity or effector, except adverse), BSU (Biological study, unclassified), SPN (Synthetic preparation), THU (Therapeutic use), BIOL (Biological study), PREP (Preparation), USES (Uses) (prepn. and antitumor activity of); 98540-27-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and dehydration of); 98540-28-4P; 98633-97-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and hydrolysis of, and O-acetylation of product from); 98540-26-2P; 98540-31-9P; 98540-32-0P; 98540-34-2P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 108-24-7 Role: RCT (Reactant), RACT (Reactant or reagent) (O-acylation by, of bis(hydroxyphenyl)butenes) | ||||
| Institutionen: | Chemie und Pharmazie > Institut für Pharmazie > Entpflichtete oder im Ruhestand befindliche Professoren > Prof. Schönenberger | ||||
| Projekte: | SFB 234 | ||||
| Identifikationsnummer: |
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| Stichwörter / Keywords: | Neoplasm inhibitors (bis(acetoxyphenyl)phenylbutenes) Estrogens Role: USES (Uses) (inhibitors, bis(acetoxyphenyl)phenylbutenes as) styrylphenyl acetate prepn antitumor antiestrogenic styrylphenylacetate prepn | ||||
| 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: | 17653 |
Zusammenfassung
1,1,2-Triphenylbut-1-enes I (R, R1, and R2 are H, OAc) which are substituted with one p- and one m-acetoxy group in two different arom. rings, were synthesized. The (E) and (Z) isomers were isolated, and their identity was established by 1H NMR spectroscopy. Among the tested compds., (E)- and (Z)-1-(3-acetoxyphenyl)-1-(4-acetoxyphenyl)-2-phenylbut-1-enes [(E)-I and (Z)-I] and ...
Zusammenfassung
1,1,2-Triphenylbut-1-enes I (R, R1, and R2 are H, OAc) which are substituted with one p- and one m-acetoxy group in two different arom. rings, were synthesized. The (E) and (Z) isomers were isolated, and their identity was established by 1H NMR spectroscopy. Among the tested compds., (E)- and (Z)-1-(3-acetoxyphenyl)-1-(4-acetoxyphenyl)-2-phenylbut-1-enes [(E)-I and (Z)-I] and (Z)-1-(3-acetoxyphenyl)-1-phenyl-2-(4-acetoxyphenyl)but-1-ene proved to be partial antiestrogens, which lead to an inhibition of the MCF7 cell line. They exert a growth-inhibiting activity on the hormone-dependent MXT mammary carcinoma of the mouse. In the case of (E)-I and (Z)-I, this effect is only slightly weaker than that of 1,1-bis(4-acetoxyphenyl)-2-phenylbut-1-ene and tamoxifen. Under the applied exptl. conditions, there were not significant changes of uterine wt. as an indicator of estrogenic side effects.
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