4-[(2R,3R,4S)-4-Methyl-6-triisopropylsilanyloxy-3-(4-triisopropylsilanyloxy-phenyl)-chroman-2-yl]-phenol | 783342-49-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 4-[(2R,3R,4S)-4-Methyl-6-triisopropylsilanyloxy-3-(4-triisopropylsilanyloxy-phenyl)-chroman-2-yl]-phenol
• CAS: 783342-49-4
• 化学式: C₄₀H₆₀O₄Si₂
• 分子量: 661.085
• InChiKey: PBRNOUNVGALREJ-VWPLQXOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.52
• 重原子数：
  46.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-[(2R,3R,4S)-4-Methyl-6-triisopropylsilanyloxy-3-(4-triisopropylsilanyloxy-phenyl)-chroman-2-yl]-phenol 在 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 生成 (2R,3R,4S)-3-(4-Hydroxy-phenyl)-4-methyl-2-[4-((R)-1-methyl-2-pyrrolidin-1-yl-ethoxy)-phenyl]-chroman-6-ol
  参考文献：
  名称：

  Estrogen receptor ligands. Part 10: Chromanes: old scaffolds for new SERAMs

  摘要：

  The discovery, synthesis, and SAR of chromanes as ER alpha subtype selective ligands are described. X-ray studies revealed that the origin of the ER alpha-selectivity resulted from a C-4 trans methyl substitution to the cis-2,3-diphenyl-chromane platform. Selected compounds from this class demonstrated very potent in vivo antagonism of estradiol in an immature rat uterine weight assay, effectively inhibited ovariectomy-induced bone resorption in a 42 days treatment paradigm, and lowered serum cholesterol levels in ovx'd adult rat models. The best antagonists 8F and 12F also exhibited potent inhibition of MCF-7 cell growth and were shown to be estrogen receptor down-regulators (SERDs).

  DOI：

  10.1016/j.bmcl.2005.01.046
• 作为产物：
  描述：

  magnesium,2-(phenoxy)oxane,bromide 在 Rh on carbon 氢气 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 4-[(2R,3R,4S)-4-Methyl-6-triisopropylsilanyloxy-3-(4-triisopropylsilanyloxy-phenyl)-chroman-2-yl]-phenol
  参考文献：
  名称：

  Estrogen receptor ligands. Part 10: Chromanes: old scaffolds for new SERAMs

  摘要：

  The discovery, synthesis, and SAR of chromanes as ER alpha subtype selective ligands are described. X-ray studies revealed that the origin of the ER alpha-selectivity resulted from a C-4 trans methyl substitution to the cis-2,3-diphenyl-chromane platform. Selected compounds from this class demonstrated very potent in vivo antagonism of estradiol in an immature rat uterine weight assay, effectively inhibited ovariectomy-induced bone resorption in a 42 days treatment paradigm, and lowered serum cholesterol levels in ovx'd adult rat models. The best antagonists 8F and 12F also exhibited potent inhibition of MCF-7 cell growth and were shown to be estrogen receptor down-regulators (SERDs).

  DOI：

  10.1016/j.bmcl.2005.01.046