17β-hydroxy-11β-[4-hydroxyphenyl]-17α-(1-propinyl)-estra-4,9-dien-3-one | 88257-21-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 17β-hydroxy-11β-[4-hydroxyphenyl]-17α-(1-propinyl)-estra-4,9-dien-3-one
• 英文别名: 17beta-Hydroxy-11beta-[4-hydroxyphenyl]-17alpha-(1-propinyl)-estra-4,9-dien-3-one；(8S,11R,13S,14S,17S)-17-hydroxy-11-(4-hydroxyphenyl)-13-methyl-17-prop-1-ynyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one
• CAS: 88257-21-0
• 化学式: C₂₇H₃₀O₃
• 分子量: 402.533
• InChiKey: ZVKZIGUVBDEZPL-YEEPMTPTSA-N

物化性质

• 沸点：
  628.7±55.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  17β-hydroxy-11β-[4-hydroxyphenyl]-17α-(1-propinyl)-estra-4,9-dien-3-one 在 palladium diacetate 、 sodium hydride 、 N,N-二异丙基乙胺 、 1,4-双(二苯基膦)丁烷 作用下， 生成 (8S,11R,13S,14S,17S)-11-(4-(diphenylphosphoryl)phenyl)-17-hydroxy-13-methyl-17-(prop-1-ynyl)-1,2,7,8,11,12,13,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3(14H)-one
  参考文献：
  名称：

  Discovery of novel phosphorus-containing steroids as selective glucocorticoid receptor antagonist

  摘要：

  Mifepristone is a non-selective antagonist of 3-oxosteroid receptors with both abortifacient and anti-diabetic activities. For glucocorticoid receptor (GR) program, we sought an unexplored, synthetically accessible phosphorus-containing steroidal mimetic of mifepristone, suitable for parallel synthesis of analogues. One compound 4a, with high oral bioavailability (59%) in rat, exhibited functional antagonism of GR in oral glucose tolerance test (OGTT). Thus this series of compounds might be potentially useful for the treatment of type II diabetes.

  DOI：

  10.1016/j.bmcl.2006.10.003
• 作为产物：
  描述：

  3-缩酮 在 对甲苯磺酸 、 间氯过氧苯甲酸 、 copper(l) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 17β-hydroxy-11β-[4-hydroxyphenyl]-17α-(1-propinyl)-estra-4,9-dien-3-one
  参考文献：
  名称：

  Discovery of novel phosphorus-containing steroids as selective glucocorticoid receptor antagonist

  摘要：

  Mifepristone is a non-selective antagonist of 3-oxosteroid receptors with both abortifacient and anti-diabetic activities. For glucocorticoid receptor (GR) program, we sought an unexplored, synthetically accessible phosphorus-containing steroidal mimetic of mifepristone, suitable for parallel synthesis of analogues. One compound 4a, with high oral bioavailability (59%) in rat, exhibited functional antagonism of GR in oral glucose tolerance test (OGTT). Thus this series of compounds might be potentially useful for the treatment of type II diabetes.

  DOI：

  10.1016/j.bmcl.2006.10.003

文献信息

• 11-PHOSPHOROUS STEROID DERIVATIVES USEFUL AS PROGESTERONE RECEPTOR MODULATORS
  申请人：Fiordeliso J. James

  公开号：US20070232570A1

  公开（公告）日：2007-10-04

  The present invention is directed to novel 11-phosphorous steroid derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by a progesterone or glucocorticoid receptor.

  本发明涉及新颖的11-磷酸类固醇衍生物，含有它们的药物组合物以及它们在治疗受孕激素或糖皮质激素受体调节的疾病和症状中的应用。
• 17-PHOSPHOROUS STEROID DERIVATIVES USEFUL AS PROGESTERONE RECEPTOR MODULATORS
  申请人：Jiang Weiqin

  公开号：US20070207982A1

  公开（公告）日：2007-09-06

  The present invention is directed to novel 17-phosphorous steroid derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by a progesterone or glucocorticoid receptor.

  本发明涉及新颖的17-磷类固醇衍生物，含有它们的药物组合物以及它们在治疗受孕激素或糖皮质激素受体调节的疾病和症状中的用途。
• Syntheses and Antigestagenic Activity of Mifepristone Derivatives
  作者：Claudia Hödl、Katrin Raunegger、Rainer Strommer、Gerhard F. Ecker、Olaf Kunert、Sonja Sturm、Christoph Seger、Ernst Haslinger、Rudolf Steiner、Wolfgang S. L. Strauss、Hans-Wolfgang Schramm

  DOI：10.1021/jm800985z

  日期：2009.3.12

  A series of mifepristone derivatives with different "linker groups" in position 4' of the phenyl ring in the 11 beta-position of the steroid scaffold (2-41) have been synthesized. Their antigestagenic activites were determined in a cell-based assay (alkali phosphatase assay in T47-D breast cancer cells) and compared with that of the parent compound mifepristone. SAR and QSAR studies reveal the influence of both lipophilicity and partial charge based van der Waals surface area descriptors on biological activity. Within the series of compounds described in this study, three n-mifepristone derivatives are identified with considerably high antigestagenic activity. These compounds are regarded as useful starting materials for the synthesis of either physiologically stable or cleavable progesterone receptor-binding conjugates for therapeutic or diagnostic purposes.
• Produit comprenant une substance antiprogestomimétique et une substance utérotonique
  申请人：ROUSSEL-UCLAF

  公开号：EP0184471B1

  公开（公告）日：1990-11-14
• US7678781B2
  申请人：——

  公开号：US7678781B2

  公开（公告）日：2010-03-16