| 162240-26-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 162240-26-8
• 化学式: C₁₃H₂₀O₄
• 分子量: 240.299
• InChiKey: LHAXGKNKFBOXKT-UTUOFQBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.26
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  在 5percent Rh/Al₂₀₃ 盐酸 、 sodium tetrahydroborate 、 氢气 、 镍 、 对甲苯磺酸 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醚 、 乙醇 、 环己烷 、 水 、 二甲基亚砜 、 乙腈 为溶剂， -78.0~20.0 ℃ 、435.73 kPa 条件下， 反应 44.0h， 生成 (1S,3aS,5S,7aR)-1-[(E)-Guanidinoimino]methyl-5-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：

  (1R,3aS,7aR)-3a-hydroxy-7a-methylperhydroindene-5-spiro-2'-(1',3'-dioxolane)-1-carboxaldehyde 在 甲醇 、 氢氧化钾 作用下， 反应 0.5h， 生成
  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

文献信息

• Synthesis and inotropic activity of hydroindene derivatives
  作者：Luis G. Sevillano、Concepción P. Melero、Melchor Boya、Jose Luis López、Fernando Tomé、Esther Caballero、Rosalı́a Carrón、M. José Montero、Manuel Medarde、Arturo San Feliciano

  DOI：10.1016/s0968-0896(99)00251-5

  日期：1999.12

  A synthetic approach to hydroindenic inotropic agents has been developed, starting from enantiopure Hajos-Parrish (1), Hajos-Wiechert (2), and related diketones. Their transformation: into C-l formyl derivatives and other subsequent synthetic targets is described. The results of the thermodynamic equilibration between both epimers of each formyl derivative are analysed. The inotropic activities of selected compounds on right and left atrial preparations are also evaluated and discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Hydroindenic-guanylhydrazones. Synthesis and evaluation as inotropic agents
  作者：Concepción P. Melero、Luis G. Sevillano、Esther Caballero、Fernando Tomé、Rosalía Carrón、M.José Montero、Arturo San Feliciano、Manuel Medarde

  DOI：10.1016/s0960-894x(98)00581-2

  日期：1998.11

  The synthesis and inotropic activity of two families of hydroindenic compounds are described. Among them, a bis-guanylhydrazone derivative has demonstrated to produce an interesting positive inotropic effect on guinea pig atria, displaying at higher dosis a similar effect to that elicited by digoxin. (C) 1998 Elsevier Science Ltd. All rights reserved.