(2aS,5aS,7S,7aS,10R,10aS,10bS,10cR)-7-ethoxy-10c-hydroxy-2a,4,4,7,10-pentamethyloctahydro-1,3,5-trioxabenzo[cd]cyclopenta[h]azulene-2,9-dione | 870133-46-3

• 分子结构分类: 有机化合物
• 英文名称: (2aS,5aS,7S,7aS,10R,10aS,10bS,10cR)-7-ethoxy-10c-hydroxy-2a,4,4,7,10-pentamethyloctahydro-1,3,5-trioxabenzo[cd]cyclopenta[h]azulene-2,9-dione
• 英文别名: (1S,2S,3R,6S,7S,9S,13S,16R)-7-ethoxy-16-hydroxy-3,7,11,11,13-pentamethyl-10,12,15-trioxatetracyclo[7.6.1.02,6.013,16]hexadecane-4,14-dione
• CAS: 870133-46-3
• 化学式: C₂₀H₃₀O₇
• 分子量: 382.454
• InChiKey: TYRMZMSOEDTWLW-QUNWNVAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2aS,5aS,7S,7aS,10R,10aS,10bS,10cR)-7-ethoxy-10c-hydroxy-2a,4,4,7,10-pentamethyloctahydro-1,3,5-trioxabenzo[cd]cyclopenta[h]azulene-2,9-dione 在 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 2,4,6-三氯苯甲酰氯 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 25.0h， 生成 (Z)-2-Methyl-but-2-enoic acid (3S,3aR,4S,6S,6aS,8R,9R,9aR,9bS)-4-butyryloxy-6-ethoxy-3,3a-dihydroxy-3,6,9-trimethyl-2-oxo-dodecahydro-azuleno[4,5-b]furan-8-yl ester
  参考文献：
  名称：

  Total Synthesis of Two Novel Subpicomolar Sarco/Endoplasmatic Reticulum Ca²⁺-ATPase Inhibitors Designed by an Analysis of the Binding Site of Thapsigargin

  摘要：

  Analysis of molecular interaction fields based on the published crystal structure of thapsigargin bound to the sarco/endoplasmatic reticulum Ca2+-ATPase and analysis of the volume and shape of the ligand binding site and of the SERCA-thapsigargin interactions have enabled design of two new compounds inhibiting SERCA in the subpicomolar range. The two inhibitors were synthesized using (S)-carvone as starting material and found to be 3 and 10 times more potent than thapsigargin.

  DOI：

  10.1021/jm058036v
• 作为产物：
  描述：

  溴乙烷 、 (1S,2S,3R,6S,7S,9S,13S,16R)-7,16-dihydroxy-3,7,11,11,13-pentamethyl-10,12,15-trioxatetracyclo[7.6.1.02,6.013,16]hexadecane-4,14-dione 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.33h， 以71%的产率得到(2aS,5aS,7S,7aS,10R,10aS,10bS,10cR)-7-ethoxy-10c-hydroxy-2a,4,4,7,10-pentamethyloctahydro-1,3,5-trioxabenzo[cd]cyclopenta[h]azulene-2,9-dione
  参考文献：
  名称：

  Total Synthesis of Two Novel Subpicomolar Sarco/Endoplasmatic Reticulum Ca²⁺-ATPase Inhibitors Designed by an Analysis of the Binding Site of Thapsigargin

  摘要：

  Analysis of molecular interaction fields based on the published crystal structure of thapsigargin bound to the sarco/endoplasmatic reticulum Ca2+-ATPase and analysis of the volume and shape of the ligand binding site and of the SERCA-thapsigargin interactions have enabled design of two new compounds inhibiting SERCA in the subpicomolar range. The two inhibitors were synthesized using (S)-carvone as starting material and found to be 3 and 10 times more potent than thapsigargin.

  DOI：

  10.1021/jm058036v