4,4'-[(4,4-dimethylcyclohexyl)methylene]bisphenol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4'-[(4,4-dimethylcyclohexyl)methylene]bisphenol
• 英文别名: 4-[(4,4-Dimethylcyclohexyl)-(4-hydroxyphenyl)methyl]phenol；4-[(4,4-dimethylcyclohexyl)-(4-hydroxyphenyl)methyl]phenol
• 化学式: C₂₁H₂₆O₂
• 分子量: 310.436
• InChiKey: RQPWVBQWFSFVLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4,4-二甲基环己酮 在 palladium 10% on activated carbon 、 氢气 、 三溴化硼 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 100.5h， 生成 4,4'-[(4,4-dimethylcyclohexyl)methylene]bisphenol
  参考文献：
  名称：

  Estrogenic activity of bis(4-hydroxyphenyl)methanes with cyclic hydrophobic structure

  摘要：

  Monoalkylated bis(4-hydroxyphenyl)methanes (e.g., 1) are reported to show weak binding affinity for estrogen receptor (ER). We hypothesized that introduction of appropriately located hydrophobic substituents in these compounds would increase the binding affinity. Indeed, we found that bis(4-hydroxyphenyl)methane bearing a 3,3-dimethylcyclohexyl group (7) shows potent ER alpha binding affinity, comparable to that of estradiol. Bulkier substituents could be introduced at the 3,3-position without decreasing the affinity. However, the position of the substituents was critical: the 4,4-dimethylcyclohexyl derivative (2) showed very weak binding affinity. The compounds with high ER-binding affinity showed predominantly agonistic activity, together with weak antagonistic activity at high concentration, in cell proliferation assay with human breast cancer cell line MCF-7. Further structure-function studies of these compounds and their derivatives might lead to the development of more selective and potent estrogen receptor modulators. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.09.046

文献信息

• Estrogenic activity of bis(4-hydroxyphenyl)methanes with cyclic hydrophobic structure
  作者：Tomohiro Kojima、Takumi Ogawa、Souichiro Kitao、Manabu Sato、Akifumi Oda、Kiminori Ohta、Yasuyuki Endo

  DOI：10.1016/j.bmc.2015.09.046

  日期：2015.11

  Monoalkylated bis(4-hydroxyphenyl)methanes (e.g., 1) are reported to show weak binding affinity for estrogen receptor (ER). We hypothesized that introduction of appropriately located hydrophobic substituents in these compounds would increase the binding affinity. Indeed, we found that bis(4-hydroxyphenyl)methane bearing a 3,3-dimethylcyclohexyl group (7) shows potent ER alpha binding affinity, comparable to that of estradiol. Bulkier substituents could be introduced at the 3,3-position without decreasing the affinity. However, the position of the substituents was critical: the 4,4-dimethylcyclohexyl derivative (2) showed very weak binding affinity. The compounds with high ER-binding affinity showed predominantly agonistic activity, together with weak antagonistic activity at high concentration, in cell proliferation assay with human breast cancer cell line MCF-7. Further structure-function studies of these compounds and their derivatives might lead to the development of more selective and potent estrogen receptor modulators. (C) 2015 Elsevier Ltd. All rights reserved.