4-[3-(4-Hydroxy-3-propylphenyl)pentan-3-yl]-2-propylphenol | 1446215-25-3

• 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-[3-(4-Hydroxy-3-propylphenyl)pentan-3-yl]-2-propylphenol
• 英文别名: 4-[3-(4-hydroxy-3-propylphenyl)pentan-3-yl]-2-propylphenol
• CAS: 1446215-25-3
• 化学式: C₂₃H₃₂O₂
• 分子量: 340.506
• InChiKey: RLOFJEMYTQIVRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 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：

  2-正丙基苯酚 、 3-戊酮 在 三氟甲磺酸 作用下， 生成 4-[3-(4-Hydroxy-3-propylphenyl)pentan-3-yl]-2-propylphenol
  参考文献：
  名称：

  Structure–activity relationships of bisphenol A analogs at estrogen receptors (ERs): Discovery of an ERα-selective antagonist

  摘要：

  Our multi-template approach for drug discovery, focusing on protein targets with similar fold structures, has yielded lead compounds for various targets. We have also shown that a diphenylmethane skeleton can serve as a surrogate for a steroid skeleton. Here, on the basis of those ideas, we hypothesized that the diphenylmethane derivative bisphenol A (BPA) would bind to the ligand-binding domain of estrogen receptors (ERs) in a similar manner to estradiol and act as a steroid surrogate. To test this idea, we synthesized a series of BPA analogs and evaluated their structure-activity relationships, focusing on agonistic/antagonistic activities at ERs and ER alpha/ER beta subtype selectivity. Among the compounds examined, 18 was found to be a potent ER alpha-antagonist with high selectivity over ER beta and androgen receptor under our assay conditions. A computational docking study suggested that 18 would bind to the antagonistic conformation of ER alpha. ER alpha-selective antagonists, such as 18, are candidate agents for treatment of breast cancer. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.067

文献信息

• Structure–activity relationships of bisphenol A analogs at estrogen receptors (ERs): Discovery of an ERα-selective antagonist
  作者：Keisuke Maruyama、Masaharu Nakamura、Shusuke Tomoshige、Kazuyuki Sugita、Makoto Makishima、Yuichi Hashimoto、Minoru Ishikawa

  DOI：10.1016/j.bmcl.2013.05.067

  日期：2013.7

  Our multi-template approach for drug discovery, focusing on protein targets with similar fold structures, has yielded lead compounds for various targets. We have also shown that a diphenylmethane skeleton can serve as a surrogate for a steroid skeleton. Here, on the basis of those ideas, we hypothesized that the diphenylmethane derivative bisphenol A (BPA) would bind to the ligand-binding domain of estrogen receptors (ERs) in a similar manner to estradiol and act as a steroid surrogate. To test this idea, we synthesized a series of BPA analogs and evaluated their structure-activity relationships, focusing on agonistic/antagonistic activities at ERs and ER alpha/ER beta subtype selectivity. Among the compounds examined, 18 was found to be a potent ER alpha-antagonist with high selectivity over ER beta and androgen receptor under our assay conditions. A computational docking study suggested that 18 would bind to the antagonistic conformation of ER alpha. ER alpha-selective antagonists, such as 18, are candidate agents for treatment of breast cancer. (C) 2013 Elsevier Ltd. All rights reserved.