(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 | 72136-99-3

• 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: (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
• CAS: 72136-99-3
• 化学式: C₂₆H₃₂O₃
• 分子量: 392.538
• InChiKey: LSKPGSZNFVVNGS-DDRRAVBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.25
• 重原子数：
  29.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  phenylmagnesium bromide 、 3-缩酮 以 四氢呋喃 为溶剂， 以85%的产率得到(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
  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