3-[11-(n-butyl-methylamino)undecyl]-6-hydroxy-2-(4-hydroxyphenyl)-benzo[b]thiophene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 3-[11-(n-butyl-methylamino)undecyl]-6-hydroxy-2-(4-hydroxyphenyl)-benzo[b]thiophene
• 英文别名: 3-[11-[Butyl(methyl)amino]undecyl]-2-(4-hydroxyphenyl)-1-benzothiophen-6-ol
• 化学式: C₃₀H₄₃NO₂S
• 分子量: 481.743
• InChiKey: VHTRJFIXASXJEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  34
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  71.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  11-溴十一酰氯 在 lithium aluminium tetrahydride 、 三氯化铝 、 三溴化硼 作用下， 以 乙醚 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 7.5h， 生成 3-[11-(n-butyl-methylamino)undecyl]-6-hydroxy-2-(4-hydroxyphenyl)-benzo[b]thiophene
  参考文献：
  名称：

  2-Phenylbenzo[b]thiophene-Based Antiestrogens with Mammary Tumor Inhibiting Activity

  摘要：

  In this study we extended our studies on heterocyclic antiestrogens to 2-phenylbenzo[b]thiophenes which can be considered as isosteric to the 2-phenylindole system. We synthesized a number of 6-hydroxy-2-(4-hydroxyphenyl)benzo [b]thiophenes with carbamoyl and amino functions in the side chain at carbon-3 and analyzed their biological properties. The binding affinities for the estrogen receptor are mainly influenced by the chain length where-as the hormonal profile depends on the nature of the functional group. From this study 3-[10-(2,2,3,3,4,4,4-heptafluorobutyl-methylcarbamoyl)decyl] -6-hydroxy- 2-(4-hydroxyphenyl)benzo-[b]thiophene (6e) emerged as an antiestrogen with all the characteristics of a pure antagonist. It did not stimulate gene expression in HeLa cells cotransfected with the expression vector for the human estrogen receptor HEG0 and the luciferase reporter plasmid EREwtc luc nor did it show any estrogenic activity in the mouse uterus weight test. In the latter assay, it completely abrogated theory effect of estrone. Due to its antiestrogenic potency it inhibited the growth of estrogen-sensitive human MCF-7 breast cancer cells with an IC50 value of 5 nM. These data suggest that an amide function in combination with the fluorination of the terminal carbon atoms is an appropriate modification to abolish the estrogenic action of the 2-phenylbenzothiophene system.

  DOI：

  10.1002/(sici)1521-4184(19989)331:9<283::aid-ardp283>3.0.co;2-n

文献信息

• 2-Phenylbenzo[b]thiophene-Based Antiestrogens with Mammary Tumor Inhibiting Activity
  作者：Stefan Leichtl、Erwin von Angerer

  DOI：10.1002/(sici)1521-4184(19989)331:9<283::aid-ardp283>3.0.co;2-n

  日期：1998.9

  In this study we extended our studies on heterocyclic antiestrogens to 2-phenylbenzo[b]thiophenes which can be considered as isosteric to the 2-phenylindole system. We synthesized a number of 6-hydroxy-2-(4-hydroxyphenyl)benzo [b]thiophenes with carbamoyl and amino functions in the side chain at carbon-3 and analyzed their biological properties. The binding affinities for the estrogen receptor are mainly influenced by the chain length where-as the hormonal profile depends on the nature of the functional group. From this study 3-[10-(2,2,3,3,4,4,4-heptafluorobutyl-methylcarbamoyl)decyl] -6-hydroxy- 2-(4-hydroxyphenyl)benzo-[b]thiophene (6e) emerged as an antiestrogen with all the characteristics of a pure antagonist. It did not stimulate gene expression in HeLa cells cotransfected with the expression vector for the human estrogen receptor HEG0 and the luciferase reporter plasmid EREwtc luc nor did it show any estrogenic activity in the mouse uterus weight test. In the latter assay, it completely abrogated theory effect of estrone. Due to its antiestrogenic potency it inhibited the growth of estrogen-sensitive human MCF-7 breast cancer cells with an IC50 value of 5 nM. These data suggest that an amide function in combination with the fluorination of the terminal carbon atoms is an appropriate modification to abolish the estrogenic action of the 2-phenylbenzothiophene system.