von Angerer E, Prekajac J
J Med Chem. 1983 Jan;26(1):113-6. doi: 10.1021/jm00355a024.
1-Alkyl-4-chloro-2-(2,6-dichloro-4-hydroxyphenyl)-6-hydroxyindoles (4, alkyl = CH3, C2H5, C3H7) were synthesized by thermolysis of the corresponding N,N'-dialkyl-1,2-diphenylethylenediamines and subsequent ether cleavage. They showed an affinity for the estrogen receptor (1% of 17 beta-estradiol) and inhibited the growth of the 9,10-dimethyl-1,2-benz[a]anthracene (DMBA) induced mammary carcinoma of the Sprague-Dawley (SD) rat. The best result was obtained by the ethyl compound (4b), which reduced the original tumor area by 50% after 4 weeks administration of 6 X 18 (mg/kg)/week. Since 4a and 4b show uterotrophic activity and cytostatic effects against hormone-independent cells, a dual mode of action has to be considered for the tumor inhibition.
通过相应的N，N'-二烷基-1,2-二苯基乙二胺的热解及随后的醚裂解反应合成了1-烷基-4-氯-2-(2,6-二氯-4-羟基苯基)-6-羟基吲哚（4，烷基 = CH3、C2H5、C3H7）。它们对雌激素受体具有亲和力（为17β-雌二醇的1%），并抑制了9,10-二甲基-1,2-苯并[a]蒽（DMBA）诱导的Sprague-Dawley（SD）大鼠乳腺癌的生长。乙基化合物（4b）取得了最佳效果，在以6×18（mg/kg）/周的剂量给药4周后，其使原始肿瘤面积减少了50%。由于4a和4b表现出子宫营养活性以及对激素非依赖性细胞的细胞抑制作用，因此在肿瘤抑制方面必须考虑其双重作用模式。
