1-[4-(2-dimethylaminoethoxy)phenyl]-3-(4-hydroxyphenyl)adamantane | 1612888-46-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1-[4-(2-dimethylaminoethoxy)phenyl]-3-(4-hydroxyphenyl)adamantane
• 英文别名: 4-[3-[4-[2-(Dimethylamino)ethoxy]phenyl]-1-adamantyl]phenol；4-[3-[4-[2-(dimethylamino)ethoxy]phenyl]-1-adamantyl]phenol
• CAS: 1612888-46-6
• 化学式: C₂₆H₃₃NO₂
• 分子量: 391.554
• InChiKey: VBWSVGQYMGKJFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4,4’-(1,3-金刚烷二基）二苯酚 、 二甲氨基氯乙烷盐酸 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以24%的产率得到1-[4-(2-dimethylaminoethoxy)phenyl]-3-(4-hydroxyphenyl)adamantane
  参考文献：
  名称：

  Novel estrogen receptor (ER) modulators containing various hydrophobic bent-core structures

  摘要：

  We previously discovered m-carborane-containing estrogen receptor (ER) modulator 4, which exhibits weak ER-agonistic and antagonistic activities in transactivation assays. With the aim of developing novel ER partial agonists, we designed and synthesized various analogues of 4 with a bent-core structure, that is, pseudo cyclic structure (5), tetrahydropyrimidinone (6), m-benzene (7), adamantane (8), and 9,1 0-dimethyl-m-carborane (9), in place of the m-carborane moiety. Compound 9 showed greater binding affinity than 4 in ER-binding assay using [6,7-H-3-17 beta-estradiol and was a more effective partial agonist than 4 in MCF-7 cell proliferation assay. It appears to be a promising candidate as a selective ER modulator (SERM). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.04.022

文献信息

• Novel estrogen receptor (ER) modulators containing various hydrophobic bent-core structures
  作者：Kiminori Ohta、Takumi Ogawa、Asako Kaise、Yasuyuki Endo

  DOI：10.1016/j.bmc.2014.04.022

  日期：2014.7

  We previously discovered m-carborane-containing estrogen receptor (ER) modulator 4, which exhibits weak ER-agonistic and antagonistic activities in transactivation assays. With the aim of developing novel ER partial agonists, we designed and synthesized various analogues of 4 with a bent-core structure, that is, pseudo cyclic structure (5), tetrahydropyrimidinone (6), m-benzene (7), adamantane (8), and 9,1 0-dimethyl-m-carborane (9), in place of the m-carborane moiety. Compound 9 showed greater binding affinity than 4 in ER-binding assay using [6,7-H-3-17 beta-estradiol and was a more effective partial agonist than 4 in MCF-7 cell proliferation assay. It appears to be a promising candidate as a selective ER modulator (SERM). (C) 2014 Elsevier Ltd. All rights reserved.