4,6,7,15,16-pentakis(acetyloxy)-18-hydroxy-20-oxo-21,22-epoxy-22-methoxycarbonyl-D:A-Friedo-A-homo-27,30-dinor-24-oxaoleana-1-ene | 223797-72-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 4,6,7,15,16-pentakis(acetyloxy)-18-hydroxy-20-oxo-21,22-epoxy-22-methoxycarbonyl-D:A-Friedo-A-homo-27,30-dinor-24-oxaoleana-1-ene
• 英文别名: methyl (1S,2R,3S,4R,5R,6S,8S,11R,12R,15S,16S,22R,23R,24S)-3,4,23,24-tetraacetyloxy-22-[(1R)-1-acetyloxyethyl]-11-hydroxy-2,5,15-trimethyl-9-oxo-7,20-dioxahexacyclo[13.9.0.02,12.05,11.06,8.016,22]tetracos-17-ene-6-carboxylate
• CAS: 223797-72-6
• 化学式: C₃₉H₅₂O₁₆
• 分子量: 776.832
• InChiKey: XWTVJVHOWQYDJX-PRMCMRGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  55
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  217
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  4,6,7,15,16-pentakis(acetyloxy)-18-hydroxy-20-oxo-21,22-epoxy-22-methoxycarbonyl-D:A-Friedo-A-homo-27,30-dinor-24-oxaoleana-1-ene 在 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
• 作为产物：
  描述：

  在 sodium periodate 作用下， 生成 4,6,7,15,16-pentakis(acetyloxy)-18-hydroxy-20-oxo-21,22-epoxy-22-methoxycarbonyl-D:A-Friedo-A-homo-27,30-dinor-24-oxaoleana-1-ene
  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

文献信息

• Novel Fragmentation Reaction of Correolide
  作者：Jianming Bao、Robert K. Baker、George A. Doss、Frank Kayser、Andrew Kotliar、Shouwu Miao、William H. Parsons、Kathleen M. Rupprecht

  DOI：10.1021/ol020053g

  日期：2002.5.1

  [reaction: see text] Pentacyclic triterpenoid natural product correolide (1) was converted to ketone 2 via ozonolysis. An unusual fragmentation reaction of ketone 2 with LiCl was discovered. This reaction is general among several similar substrates examined and appears to be specific for the correolide-type E-ring structure (ketone). A mechanism involving a retroaldol reaction, a nucleophilic opening

  [反应：见正文]五环三萜类天然产物Correolide（1）通过臭氧分解转化为酮2。发现酮2与LiCl发生不寻常的断裂反应。该反应在所检查的几种相似的底物中是普遍的，并且似乎是对correolide型E环结构（酮）特异的。提出了涉及逆醛醇缩合反应，环氧化物的亲核开环和随后的乙酰氧基消除反应的机理。