Acetic acid (1R,4R,4aR,4bS,5S,6R,6aR,11aS,11bS,13aR)-5,6-diacetoxy-6a-((R)-1-acetoxy-ethyl)-1-hydroxy-2,4a,11b-trimethyl-1-(2-phenyl-allyl)-1,4,4a,4b,5,6,6a,7,9,11a,11b,12,13,13a-tetradecahydro-8-oxa-cyclohepta[a]phenanthren-4-yl ester | 223798-33-2

• 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: Acetic acid (1R,4R,4aR,4bS,5S,6R,6aR,11aS,11bS,13aR)-5,6-diacetoxy-6a-((R)-1-acetoxy-ethyl)-1-hydroxy-2,4a,11b-trimethyl-1-(2-phenyl-allyl)-1,4,4a,4b,5,6,6a,7,9,11a,11b,12,13,13a-tetradecahydro-8-oxa-cyclohepta[a]phenanthren-4-yl ester
• CAS: 223798-33-2
• 化学式: C₄₀H₅₂O₁₀
• 分子量: 692.847
• InChiKey: KTLGTZSYLYAMTB-MLRIGIRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.77
• 重原子数：
  50.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  134.66
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (1R,4R,4aR,4bS,5S,6R,6aR,11aS,11bS,13aR)-5,6-diacetoxy-6a-((R)-1-acetoxy-ethyl)-1-hydroxy-2,4a,11b-trimethyl-1-(2-phenyl-allyl)-1,4,4a,4b,5,6,6a,7,9,11a,11b,12,13,13a-tetradecahydro-8-oxa-cyclohepta[a]phenanthren-4-yl ester 在 Wilkinson's catalyst 氢气 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 反应 23.0h， 生成 、 Acetic acid (1R,4R,4aR,4bS,5S,6R,6aR,11aS,11bS,13aR)-5,6-diacetoxy-6a-((R)-1-acetoxy-ethyl)-1-hydroxy-2,4a,11b-trimethyl-1-((R)-2-phenyl-propyl)-1,4,4a,4b,5,6,6a,7,9,11a,11b,12,13,13a-tetradecahydro-8-oxa-cyclohepta[a]phenanthren-4-yl ester
  参考文献：
  名称：

  Potent Kv1.3 inhibitors from correolide—modification of the C18 position

  摘要：

  Kv1.3, the voltage-gated potassium channel in human T cells, represents a new target for treating immunosuppression and autoimmune diseases. Correolide (1), a pentacyclic natural product, is a potent and selective Kv1.3 channel blocker. Simplification of correolide via removal of its E-ring generates enone 4, whose modification produced a new series of tetracyclic Kv1.3 blockers. The structure-activity relationship for this class of compounds in two functional assays, Rb_Kv and human T cell proliferation, is presented herein. The most potent analog 43 is 15-fold more potent than correolide as inhibitor of human T cell proliferation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.058
• 作为产物：
  描述：

  在 sodium periodate 、 四氯化钛 、 lithium chloride 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 17.0h， 生成 Acetic acid (1R,4R,4aR,4bS,5S,6R,6aR,11aS,11bS,13aR)-5,6-diacetoxy-6a-((R)-1-acetoxy-ethyl)-1-hydroxy-2,4a,11b-trimethyl-1-(2-phenyl-allyl)-1,4,4a,4b,5,6,6a,7,9,11a,11b,12,13,13a-tetradecahydro-8-oxa-cyclohepta[a]phenanthren-4-yl ester
  参考文献：
  名称：

  Potent Kv1.3 inhibitors from correolide—modification of the C18 position

  摘要：

  Kv1.3, the voltage-gated potassium channel in human T cells, represents a new target for treating immunosuppression and autoimmune diseases. Correolide (1), a pentacyclic natural product, is a potent and selective Kv1.3 channel blocker. Simplification of correolide via removal of its E-ring generates enone 4, whose modification produced a new series of tetracyclic Kv1.3 blockers. The structure-activity relationship for this class of compounds in two functional assays, Rb_Kv and human T cell proliferation, is presented herein. The most potent analog 43 is 15-fold more potent than correolide as inhibitor of human T cell proliferation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.058