(R)-(+)-7,9-difluoro-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-oxa-chrysen-2-ol | 861931-48-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: (R)-(+)-7,9-difluoro-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-oxa-chrysen-2-ol
• 英文别名: (R)-(+)-7,9-difluoro-5-[4-(2-piperidin-1-ylethoxy)phenyl]-5H-6-oxachrysen-2-ol hydrochloride；(5R)-7,9-difluoro-5-[4-(2-piperidin-1-ylethoxy)phenyl]-5H-naphtho[1,2-c]chromen-2-ol
• CAS: 861931-48-8
• 化学式: C₃₀H₂₇F₂NO₃
• 分子量: 487.546
• InChiKey: AKRKKOYYGGSJRD-GDLZYMKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  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

文献信息

• [EN] SELECTIVE ESTROGEN RECEPTOR MODULATORS FOR THE TREATMENT OF VASOMOTOR SYMPTOMS<br/>[FR] MODULATEURS SELECTIFS DU RECEPTEUR DES OESTROGENES POUR LE TRAITEMENT DE SYMPTOMES VASOMOTEURS
  申请人：LILLY CO ELI

  公开号：WO2005073204A1

  公开（公告）日：2005-08-11

  The present invention relates to a selective estrogen receptor modulator of formula I or Ia: (I) (Ia); or a pharmaceutical acid addition salt thereof; useful for treating vasomotor symptoms, in particular hot flashes, night sweats and other symptoms that affect women around menopause.

  本发明涉及一种公式I或Ia的选择性雌激素受体调节剂：(I) (Ia)；或其药物酸加成盐；用于治疗血管舒缩症状，尤其是热潮红、夜间出汗以及影响绝经前后妇女的其他症状。
• 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.