5-{hydroxy-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methyl}-6-(2,3,5-trifluoro-phenyl)-naphthalen-2-ol | 874486-74-5

• 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: 5-{hydroxy-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methyl}-6-(2,3,5-trifluoro-phenyl)-naphthalen-2-ol
• 英文别名: 5-[(R)-hydroxy-[4-(2-piperidin-1-ylethoxy)phenyl]methyl]-6-(2,3,5-trifluorophenyl)naphthalen-2-ol
• CAS: 874486-74-5
• 化学式: C₃₀H₂₈F₃NO₃
• 分子量: 507.552
• InChiKey: MHCVXZOYAYUXSO-SSEXGKCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  52.9
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-{hydroxy-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methyl}-6-(2,3,5-trifluoro-phenyl)-naphthalen-2-ol 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以97%的产率得到(R)-(+)-7,9-difluoro-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-oxa-chrysen-2-ol
  参考文献：
  名称：

  A Selective Estrogen Receptor Modulator for the Treatment of Hot Flushes

  摘要：

  A selective estrogen receptor modulator (SERM) for the potential treatment of hot flushes is described. (R)-(+)-7,9-difluoro-5-[4-(2-piperidin-1-ylethoxy)phenyl]-5H-6-oxachrysen-2-ol, LSN2120310, potently binds ER alpha and ER beta and is an antagonist in MCF-7 breast adenocarcinoma and Ishikawa uterine cancer cell lines. The compound is a potent estrogen antagonist in the rat uterus. In ovariectomized rats, the compound lowers cholesterol, maintains bone mineral density, and is efficacious in a morphine dependent rat model of hot flush efficacy.

  DOI：

  10.1021/jm0509795
• 作为产物：
  描述：

  4-(2-哌啶乙氧基)苯甲酸盐酸盐 在 吡啶 、 盐酸 、 三氯化铝 、 硼烷四氢呋喃络合物 、 2-甲基-2-丁烯 、 bis(acetato)bis(triphenylphosphine)palladium 、 三溴化硼 、 (R)-(+)-alpha,alpha-二苯基脯氨醇 、 C.I.酸性橙108 、 N,N-二异丙基乙胺 、 cesium fluoride 、 联硼酸新戊二醇酯 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 7.33h， 生成 5-{hydroxy-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methyl}-6-(2,3,5-trifluoro-phenyl)-naphthalen-2-ol
  参考文献：
  名称：

  A Selective Estrogen Receptor Modulator for the Treatment of Hot Flushes

  摘要：

  A selective estrogen receptor modulator (SERM) for the potential treatment of hot flushes is described. (R)-(+)-7,9-difluoro-5-[4-(2-piperidin-1-ylethoxy)phenyl]-5H-6-oxachrysen-2-ol, LSN2120310, potently binds ER alpha and ER beta and is an antagonist in MCF-7 breast adenocarcinoma and Ishikawa uterine cancer cell lines. The compound is a potent estrogen antagonist in the rat uterus. In ovariectomized rats, the compound lowers cholesterol, maintains bone mineral density, and is efficacious in a morphine dependent rat model of hot flush efficacy.

  DOI：

  10.1021/jm0509795

文献信息

• A Selective Estrogen Receptor Modulator for the Treatment of Hot Flushes
  作者：Owen B. Wallace、Kenneth S. Lauwers、Jeffrey A. Dodge、Scott A. May、Joel R. Calvin、Ronald Hinklin、Henry U. Bryant、Pamela K. Shetler、Mary D. Adrian、Andrew G. Geiser、Masahiko Sato、Thomas P. Burris

  DOI：10.1021/jm0509795

  日期：2006.2.1

  A selective estrogen receptor modulator (SERM) for the potential treatment of hot flushes is described. (R)-(+)-7,9-difluoro-5-[4-(2-piperidin-1-ylethoxy)phenyl]-5H-6-oxachrysen-2-ol, LSN2120310, potently binds ER alpha and ER beta and is an antagonist in MCF-7 breast adenocarcinoma and Ishikawa uterine cancer cell lines. The compound is a potent estrogen antagonist in the rat uterus. In ovariectomized rats, the compound lowers cholesterol, maintains bone mineral density, and is efficacious in a morphine dependent rat model of hot flush efficacy.