(1'R,5'S,6'S,9'S,10'S,13'R)-5'-methyl-6'-phenylspiro[1,3-dioxolane-2,15'-18-oxapentacyclo[11.4.1.01,13.02,10.05,9]octadec-2-ene]-6'-ol | 934415-52-8

• 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: (1'R,5'S,6'S,9'S,10'S,13'R)-5'-methyl-6'-phenylspiro[1,3-dioxolane-2,15'-18-oxapentacyclo[11.4.1.01,13.02,10.05,9]octadec-2-ene]-6'-ol
• CAS: 934415-52-8
• 化学式: C₂₆H₃₂O₄
• 分子量: 408.538
• InChiKey: WXBZKGMEBAVOCT-JZPIJGDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1'R,5'S,6'S,9'S,10'S,13'R)-5'-methyl-6'-phenylspiro[1,3-dioxolane-2,15'-18-oxapentacyclo[11.4.1.01,13.02,10.05,9]octadec-2-ene]-6'-ol 在 palladium diacetate 、 sodium hydride 、 对甲苯磺酸 、 N,N-二异丙基乙胺 、 1,4-双(二苯基膦)丁烷 、 copper(l) chloride 作用下， 以 四氢呋喃 为溶剂， 生成 (8S,11R,13S,14S,17S)-11-(4-(diphenylphosphoryl)phenyl)-17-hydroxy-13-methyl-17-phenyl-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：

  (8S,13S,14S,17S)-13-methyl-17-phenyl-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17-ol 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以35%的产率得到(1'R,5'S,6'S,9'S,10'S,13'R)-5'-methyl-6'-phenylspiro[1,3-dioxolane-2,15'-18-oxapentacyclo[11.4.1.01,13.02,10.05,9]octadec-2-ene]-6'-ol
  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。
• US7678781B2
  申请人：——

  公开号：US7678781B2

  公开（公告）日：2010-03-16