Angerer, Erwin von and Egginger, Guenter and Kranzfelder, Gerhard and Bernhauer, Horst and Schönenberger, Helmut (1982) N,N'-Dialkyl-1,2-bis(hydroxyphenyl)ethylenediamines and N,N-dialkyl-4,5-bis(4-hydroxyphenyl)imidazolidines: syntheses and evaluation of their mammary tumor inhibiting activity. Journal of medicinal chemistry 25 (7), pp. 832-837.
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Diastereomeric N,N'-dialkyl-1,2-bis(hydroxyphenyl)ethylenediamines (5) were synthesized and tested for their affinity for the estradiol receptor. Only the (+/-)-1,2-bis(4-hydroxyphenyl)ethylenediamines with the alkyl groups C₃H₇ [(+/-)-5c, Ka = 1.1 x 19(6))], C₄H₉ [(+/-)-5e,Ka = 3.6 x 10(6)], and C₅H₁₁ [(+/-)-5h, Ka = 2.2 x 10(6)] showed a marked affinity, which is mainly due to the (+) enantiomers [e.g., (+)-5e, Ka = 2.1 x 10(7)]. No enhancement of affinity by cyclization to imidazolidines [e.g., (+/-)-trans-7a, Ka = 1.2 x 10(7)] was observed. These compounds [e.g., (+/-)-, (+)-, and (-)-5e], which did not produce any uterine response in the mouse, were able to inhibit weakly the growth of the DMBA-induced mammary carcinoma of the rat. The inhibitory effect of (+/-)-5e against MCF-7 cells, which can be overcome by hexestrol, makes a direct antiestrogenic mode of action probable, since general cytotoxic effects and a central action could be ruled out.
|Institutions:|| Chemistry and Pharmacy > Institute of Pharmacy > Retired Professors > Prof. Schönenberger|
Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical/Medicinal Chemistry II (Prof. Buschauer)
|Subjects:||500 Science > 570 Life sciences|
500 Science > 540 Chemistry & allied sciences
600 Technology > 610 Medical sciences Medicine
|Refereed:||Yes, this version has been refereed|
|Created at the University of Regensburg:||Yes|
|Owner:||Prof. Armin Buschauer|
|Deposited On:||03 Nov 2008 15:23|
|Last Modified:||19 Aug 2010 12:09|