Synthesis and biological evaluation of p
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- 作者：Takumi Ogawa ; Kiminori Ohta ; Toru Iijima ; Tomoharu Suzuki ; Shigeru Ohta ; Yasuyuki Endo
- 关键词：Estrogen receptor ; Agonists ; Carborane ; Phenols ; Structure– ; activity relationship
- 刊名：Bioorganic and Medicinal Chemistry
- 出版年：2009
- 出版时间：1 February 2009
- 年：2009
- 卷：17
- 期：3
- 页码：1109-1117
- 全文大小：566 K
文摘
p-Carborane bisphenols and their derivatives were prepared and evaluated for binding affinity to estrogen receptor α. Their estrogenic activity was evaluated by means of transcriptional assay and cell proliferation assay using MCF-7 cell lines. 1,12-Bis(4-hydroxyphenyl)-1,12-dicarba-closo-dodecaborane 4a showed potent estrogenic activity, approaching that of 17β-estradiol, in transactivation assay. The activity of isomers 5a and 6a was drastically affected by the change in the position of one of the hydroxyl groups; 6a (ortho-OH in one ring) was about 1000 times less potent than 4a. Modification of this hydroxyl group with alkyl groups decreased the estrogenic activity in all isomers. Compound 4a also showed potent MCF-7 cell proliferation-enhancing activity.