(1R,3aR,4R,6aS,6bS)-1-(4-(dimethylamino)phenyl)-3a-methyl-4-(prop-1-yn-1-yl)-3a,4,5,6,6a,6b,7,8,11,12-decahydro-1H,3H-spiro[cyclopenta[c]naphtho[2,1-e]oxepine-10,2'-[1,3]dioxolan]-4-ol | 946849-21-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: (1R,3aR,4R,6aS,6bS)-1-(4-(dimethylamino)phenyl)-3a-methyl-4-(prop-1-yn-1-yl)-3a,4,5,6,6a,6b,7,8,11,12-decahydro-1H,3H-spiro[cyclopenta[c]naphtho[2,1-e]oxepine-10,2'-[1,3]dioxolan]-4-ol
• CAS: 946849-21-4
• 化学式: C₃₁H₃₉NO₄
• 分子量: 489.655
• InChiKey: QGLCBRMAFYHNGN-KRVZZJCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.16
• 重原子数：
  36.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  51.16
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1R,3aR,4R,6aS,6bS)-1-(4-(dimethylamino)phenyl)-3a-methyl-4-(prop-1-yn-1-yl)-3a,4,5,6,6a,6b,7,8,11,12-decahydro-1H,3H-spiro[cyclopenta[c]naphtho[2,1-e]oxepine-10,2'-[1,3]dioxolan]-4-ol 在 水 、 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 12.0h， 生成 (1S,2S,5R,6R,9R)-9-[4-(dimethylamino)phenyl]-5-hydroxy-6-methyl-5-prop-1-ynyl-8-oxatetracyclo[8.8.0.02,6.011,16]octadeca-10,15-dien-14-one
  参考文献：
  名称：

  Synthesis and SAR study of novel pseudo-steroids as potent and selective progesterone receptor antagonists

  摘要：

  Synthesis of novel 7-pseudo-steroids 1c has been achieved from trenbolone 3 via an efficient 14 step sequence with overall yields of 10-15%. Various substitutions were incorporated at both the aromatic side chain as well as the D ring. The orientation of aromatic side chain at C10 plays a crucial role for progesterone receptor (PR) activity. Compound 2a (T47D = 1 nM) with -NMe2 para to the aromatic group along with spirofurane groups in the D ring was the optimal substitution. All compounds were also evaluated for glucocorticoid receptor (GR) antagonist activities in vivo in a rat and found efficacious in uterine complement C3 assay via the oral route of administrations. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.095
• 作为产物：
  描述：

  (1R,3aR,6aS,6bS)-1-(4-(dimethylamino)phenyl)-3a-methyl-3,3a,5,6,6a,6b,7,8,11,12-decahydro-1H,4H-spiro[cyclopenta[c]naphtho[2,1-e]oxepine-10,2'-[1,3]dioxolan]-4-one 、 1-丙炔溴化镁 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 (1R,3aR,4R,6aS,6bS)-1-(4-(dimethylamino)phenyl)-3a-methyl-4-(prop-1-yn-1-yl)-3a,4,5,6,6a,6b,7,8,11,12-decahydro-1H,3H-spiro[cyclopenta[c]naphtho[2,1-e]oxepine-10,2'-[1,3]dioxolan]-4-ol
  参考文献：
  名称：

  Synthesis and SAR study of novel pseudo-steroids as potent and selective progesterone receptor antagonists

  摘要：

  Synthesis of novel 7-pseudo-steroids 1c has been achieved from trenbolone 3 via an efficient 14 step sequence with overall yields of 10-15%. Various substitutions were incorporated at both the aromatic side chain as well as the D ring. The orientation of aromatic side chain at C10 plays a crucial role for progesterone receptor (PR) activity. Compound 2a (T47D = 1 nM) with -NMe2 para to the aromatic group along with spirofurane groups in the D ring was the optimal substitution. All compounds were also evaluated for glucocorticoid receptor (GR) antagonist activities in vivo in a rat and found efficacious in uterine complement C3 assay via the oral route of administrations. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.095