((1S,3aR,4S,6aS,6bS,12aS,12bR)-12b-fluoro-12a-methyl-5,6,6a,6b,7,9,11,12,12a,12b-decahydro-1H,3H,4H-spiro[[1,3a]methanocyclopenta[c]naphtho[2,1-e]oxepine-10,2'-[1,3]dioxolan]-4-yl)methanol | 95069-41-3

• 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: ((1S,3aR,4S,6aS,6bS,12aS,12bR)-12b-fluoro-12a-methyl-5,6,6a,6b,7,9,11,12,12a,12b-decahydro-1H,3H,4H-spiro[[1,3a]methanocyclopenta[c]naphtho[2,1-e]oxepine-10,2'-[1,3]dioxolan]-4-yl)methanol
• CAS: 95069-41-3
• 化学式: C₂₂H₃₁FO₄
• 分子量: 378.484
• InChiKey: LHWPWGULMLSTSR-IIWZJXAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  27.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ((1S,3aR,4S,6aS,6bS,12aS,12bR)-12b-fluoro-12a-methyl-5,6,6a,6b,7,9,11,12,12a,12b-decahydro-1H,3H,4H-spiro[[1,3a]methanocyclopenta[c]naphtho[2,1-e]oxepine-10,2'-[1,3]dioxolan]-4-yl)methanol 在 dipyridine chromium trioxide 作用下， 以 二氯甲烷 为溶剂， 生成 3,3-(ethylenedioxy)-9α-fluoro-17β-formyl-11β,18-epoxyandrost-5-ene
  参考文献：
  名称：

  Aldosterone antagonists. 1. Synthesis and biological activities of 11.beta.,18-epoxypregnane derivatives

  摘要：

  Several steroid derivatives having the 11 beta,18-epoxypregnane skeleton, 7, 8, 19, 20, 21, and 31, were synthesized to evaluate their antialdosterone activity. Among them, 3-(9 alpha-fluoro-17 beta-hydroxy-3-oxoandrost-4-en-17 alpha-yl)propionic acid gamma-lactone (31) possessed fairly strong binding affinity for the cytoplasmic mineralocorticoid receptor of rat kidney and exhibited good aldosterone antagonist activity in an in vivo assay. However, its agonistic nature cannot be ignored. The properties of 31 as an aldosterone antagonist were enhanced by its very low to negligible binding affinity for the androgen, progestin, estrogen, and glucocorticoid receptors.

  DOI：

  10.1021/jm00382a007
• 作为产物：
  描述：

  在 二异丁基氢化铝 、 对甲苯磺酸 作用下， 以 乙醚 、 乙酸乙酯 、 甲苯 、 苯 为溶剂， 反应 4.75h， 生成 ((1S,3aR,4S,6aS,6bS,12aS,12bR)-12b-fluoro-12a-methyl-5,6,6a,6b,7,9,11,12,12a,12b-decahydro-1H,3H,4H-spiro[[1,3a]methanocyclopenta[c]naphtho[2,1-e]oxepine-10,2'-[1,3]dioxolan]-4-yl)methanol
  参考文献：
  名称：

  Aldosterone antagonists. 1. Synthesis and biological activities of 11.beta.,18-epoxypregnane derivatives

  摘要：

  Several steroid derivatives having the 11 beta,18-epoxypregnane skeleton, 7, 8, 19, 20, 21, and 31, were synthesized to evaluate their antialdosterone activity. Among them, 3-(9 alpha-fluoro-17 beta-hydroxy-3-oxoandrost-4-en-17 alpha-yl)propionic acid gamma-lactone (31) possessed fairly strong binding affinity for the cytoplasmic mineralocorticoid receptor of rat kidney and exhibited good aldosterone antagonist activity in an in vivo assay. However, its agonistic nature cannot be ignored. The properties of 31 as an aldosterone antagonist were enhanced by its very low to negligible binding affinity for the androgen, progestin, estrogen, and glucocorticoid receptors.

  DOI：

  10.1021/jm00382a007