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Cytotoxic Estrogens: Anilin Mustard Linked 1,1,2‐Triphenylbut‐1‐enes with Mammary Tumor Inhibiting Activity
Author(s) -
Schneider Martin R.,
Schuderer Michael L.
Publication year - 1989
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19893220114
Subject(s) - chemistry , moiety , cytotoxic t cell , receptor , cell culture , estrogen receptor , mammary carcinoma , mammary gland , hormone receptor , hormone , ring (chemistry) , cancer research , medicine , stereochemistry , endocrinology , biochemistry , cancer , breast cancer , in vitro , biology , carcinoma , organic chemistry , genetics
In order to develop cytotoxic estrogens with a specific effect on hormone‐dependent mammary tumors, two 1,1,2‐triphenylbut‐1‐enes with a 4‐OH group at one C‐1‐phenyl ring and a chloro‐[ 4 ] or bromo‐[ 8 ] anilin mustard moiety at the other C‐1‐phenyl ring were synthesized. 4 and 8 exerted strong alkylating activity and an irreversible binding to the estrogen receptor. In spite of relatively low receptor affinities, both anilin mustards exhibited a better effect on a receptor‐positive breast cancer cell line as well as on a hormone‐dependent mammary carcinoma of the mouse than on a receptor‐negative cell line and a hormone‐independent mammary carcinoma. Therefore, a selective antitumor activity of 4 and 8 is likely.