Erber, S. and Ringshandl, R. and Angerer, E. von (1991) 2-Phenylbenzo[b]furans: relationship between structure, estrogen receptor affinity and cytostatic activity against mammary tumor cells. Anti-cancer drug design 6 (5), pp. 417-426.
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A number of 2-(4-hydroxyphenyl)benzo[b]furans with a hydroxy group in position 5 or 6 and a short alkyl group at C-3 were synthesized from appropriate 1,2-diarylethanones and studied for their estrogen receptor affinity. The relative binding affinities in the 5-hydroxy series were higher than those of 6-hydroxy derivatives by a factor of 10. The trifluoroethyl and the propyl derivatives displayed the best relative binding affinity values (33 (15a) and 20 (12a); 17 beta-estradiol = 100). All benzofurans with high receptor affinity were tested for specific cytostatic activity using hormone-sensitive human MCF-7 mammary tumor cells and hormone-independent MDA-MB 231 cells. 5-Hydroxy derivatives with an ethyl (11a) or a propyl (12a) group completely inhibited the growth of MCF-7 cells at a concentration of 5 microM (tamoxifen: 70% inhibition). Since the cytostatic activity in MDA-MB 231 cells was much lower, an anti-tumor effect mainly mediated by the estrogen receptor has to be assumed. In the mouse uterine weight test these compounds gave rise to a partial estrogen antagonism which may account for the inhibitory effect in estrogen-sensitive tumor cells.
|Institutions:||Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical/Medicinal Chemistry II (Prof. Buschauer)|
|Subjects:||500 Science > 570 Life sciences|
500 Science > 540 Chemistry & allied sciences
|Refereed:||Yes, this version has been refereed|
|Created at the University of Regensburg:||Yes|
|Owner:||Prof. Armin Buschauer|
|Deposited On:||10 Dec 2008 14:39|
|Last Modified:||05 Aug 2009 13:48|