(1S,3aS,5S,7aR)-1-acetoxymethyl-5-(4-trans-hydroxy-1-cyclohexyl)-7a-methylperhydroindene-3a-ol | 392235-31-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,3aS,5S,7aR)-1-acetoxymethyl-5-(4-trans-hydroxy-1-cyclohexyl)-7a-methylperhydroindene-3a-ol
• CAS: 392235-31-3
• 化学式: C₁₉H₃₂O₄
• 分子量: 324.461
• InChiKey: QTFRWHBKFZUAHL-UESMBRTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S,3aS,5S,7aR)-1-acetoxymethyl-5-(4-trans-hydroxy-1-cyclohexyl)-7a-methylperhydroindene-3a-ol 在 咪唑 、 盐酸 、 sodium acetate 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 (1S,3aS,5S,7aR)-1-[2-dimethylaminoethoxy-(E)-iminomethyl]-5-(4-trans-hydroxy-r-1-cyclohexyl)-7a-methylperhydroinden-3a-ol
  参考文献：
  名称：

  Synthesis and Inotropic Activity of 1-(O-Aminoalkyloximes) of Perhydroindene Derivatives as Simplified Digitalis-like Compounds Acting on the Na⁺,K⁺-ATPase

  摘要：

  A series of 5-substituted (3aS,7aR)-7a-methylperhydroinden-3a-ol derivatives bearing a 1(S)(omega-aminoalkoxy)iminoalkyl or -alkenyl substituent was synthesized, starting from the Hajos-Parrish ketol 47, as simplified analogues of very potent 17beta-aminoalkyloximes with digitalis skeleton, previously reported. The target compounds were evaluated in vitro for displacement of the specific [H-3]ouabain binding from the dog kidney Na+,K+-ATPase receptor. Some of them revealed IC50 values in the micromolar range. The most active compounds possess a cyclohexyl group in the 5(S) position and in position 1(S) the same aminoalkyloxime groups already reported for the digitoxigenin-like series in position 17beta. Although the ring conformation of these derivatives was comparable to that of uzarigenin, the binding affinities of the most active ones were 4/8-fold lower in comparison to that standard, Three compounds among those with the highest affinities were assayed in vitro for their inotropic activity on an electrically driven guinea pig left atrium and were found to be less potent than both digoxin, the most widely used inotropic agent, and the corresponding digitalis 17beta-aminoalkyloximes.

  DOI：

  10.1021/jm011001k
• 作为产物：
  描述：

  (+)-六氢-3a-羟基-7a-甲基-1H-茚-1,5(6H)-二酮 在 5percent Rh/Al₂O₃ 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 正丁基锂 、 Ranye-Ni 、 硼烷 、 potassium tert-butylate 、 氢气 、 草酸 、 对甲苯磺酸 、 lithium tri-t-butoxyaluminum hydride 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 正己烷 、 水 、 乙腈 、 叔丁醇 为溶剂， -78.0~20.0 ℃ 、435.73 kPa 条件下， 反应 111.0h， 生成 (1S,3aS,5S,7aR)-1-acetoxymethyl-5-(4-trans-hydroxy-1-cyclohexyl)-7a-methylperhydroindene-3a-ol
  参考文献：
  名称：

  Synthesis and Inotropic Activity of 1-(O-Aminoalkyloximes) of Perhydroindene Derivatives as Simplified Digitalis-like Compounds Acting on the Na⁺,K⁺-ATPase

  摘要：

  A series of 5-substituted (3aS,7aR)-7a-methylperhydroinden-3a-ol derivatives bearing a 1(S)(omega-aminoalkoxy)iminoalkyl or -alkenyl substituent was synthesized, starting from the Hajos-Parrish ketol 47, as simplified analogues of very potent 17beta-aminoalkyloximes with digitalis skeleton, previously reported. The target compounds were evaluated in vitro for displacement of the specific [H-3]ouabain binding from the dog kidney Na+,K+-ATPase receptor. Some of them revealed IC50 values in the micromolar range. The most active compounds possess a cyclohexyl group in the 5(S) position and in position 1(S) the same aminoalkyloxime groups already reported for the digitoxigenin-like series in position 17beta. Although the ring conformation of these derivatives was comparable to that of uzarigenin, the binding affinities of the most active ones were 4/8-fold lower in comparison to that standard, Three compounds among those with the highest affinities were assayed in vitro for their inotropic activity on an electrically driven guinea pig left atrium and were found to be less potent than both digoxin, the most widely used inotropic agent, and the corresponding digitalis 17beta-aminoalkyloximes.

  DOI：

  10.1021/jm011001k