Schneider, Martin R. and Schönenberger, Helmut and Michel, Ralf T. and Fortmeyer, H. P. (1982) Mammary tumor inhibiting effect of 3,3'-diacetoxy-alpha ,beta -dialkylstilbenes and of related stilbene oxides. Journal of medicinal chemistry 25 (2), pp. 141-145.
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3,3'-Diacetoxy-alpha ,beta -dialkylstilbenes (C1-4 alkyl), 3,3'-dihydroxy-alpha ,beta -diethylstilbene (I) [80149-87-7], and their corresponding stilbene oxides were synthesized. These compds. competitively antagonized in vitro the interaction of 3H-labeled estradiol [50-28-2] with its receptor. 3,3'-diacetoxy-alpha ,beta -diethylstilbene [80149-84-4], 3,3'-diacetoxy-alpha ,beta -diethylstilbene oxide [80149-88-8] And their phenolic analogs were most effective. Shortening or lengthening the alkyl side chains led to a decrease in receptor affinity. Among the stilbenes and epoxides, those with C2H5 and C3H7 groups caused the strongest inhibition of the growth of a hormone-dependent postmenopausal human mammary carcinoma serially implanted in nude mice. The strong antitumor activity of I and its epoxide (II) [80149-95-7] was confirmed by expts. on the DMBA-induced, hormone-dependent mammary carcinoma of the Sprague-Dawley rat.
|Additional information (public):||CAN 96:46387 2-2 Mammalian Hormones 80149-92-4; 80149-93-5; 80149-94-6 Role: RCT (Reactant), RACT (Reactant or reagent) (acetylation of); 78515-20-5P; 80149-84-4P; 80149-85-5P; 80149-86-6P; 80149-87-7P; 80149-88-8P; 80149-89-9P; 80149-90-2P; 80149-91-3P; 80149-95-7P 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 neoplasm-inhibiting activity of); 50-28-2 Role: BIOL (Biological study) (receptor binding of, stilbene derivs. inhibition of)|
|Institutions:||Chemistry and Pharmacy > Institute of Pharmacy > Retired Professors > Prof. Schönenberger|
|Keywords:||Receptors Role: PROC (Process) (for estrogen, stilbene derivs. antagonism of) Estrogens Role: BIOL (Biological study) (receptor for, stilbene derivs. antagonism of) Neoplasm inhibitors (stilbene derivs. as) Mammary gland (neoplasm, stilbene derivs. inhibition of) Molecular structure-biological activity relationship (neoplasm-inhibiting, of stilbene derivs.) mammary neoplasm inhibitor stilbene structure activity stilbene|
|Subjects:||500 Science > 540 Chemistry & allied sciences|
|Refereed:||Yes, this version has been refereed|
|Created at the University of Regensburg:||Yes|
|Deposited On:||12 Nov 2010 10:14|
|Last Modified:||12 Nov 2010 10:14|
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