(3S,3'S,4'R,6'S,8'R,8'aR)-N-(1H-benzimidazol-2-ylmethyl)-5-(4-hydroxybut-1-ynyl)-6'-[3-(2-hydroxyethoxy)phenyl]-1',2-dioxo-3',4'-diphenylspiro[1H-indole-3,7'-4,6,8,8a-tetrahydro-3H-pyrrolo[2,1-c][1,4]oxazine]-8'-carboxamide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (3S,3'S,4'R,6'S,8'R,8'aR)-N-(1H-benzimidazol-2-ylmethyl)-5-(4-hydroxybut-1-ynyl)-6'-[3-(2-hydroxyethoxy)phenyl]-1',2-dioxo-3',4'-diphenylspiro[1H-indole-3,7'-4,6,8,8a-tetrahydro-3H-pyrrolo[2,1-c][1,4]oxazine]-8'-carboxamide
• 化学式: C₄₇H₄₁N₅O₇
• 分子量: 787.872
• InChiKey: JEXRZYQECXKXFO-LXWWIJTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  59
• 可旋转键数：
  11
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  166
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  5-碘吲哚醌 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 Mg(ClO)4 、 三乙胺 、 lithium bromide 、 原甲酸三甲酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 168.0h， 生成 (3S,3'S,4'R,6'S,8'R,8'aR)-N-(1H-benzimidazol-2-ylmethyl)-5-(4-hydroxybut-1-ynyl)-6'-[3-(2-hydroxyethoxy)phenyl]-1',2-dioxo-3',4'-diphenylspiro[1H-indole-3,7'-4,6,8,8a-tetrahydro-3H-pyrrolo[2,1-c][1,4]oxazine]-8'-carboxamide
  参考文献：
  名称：

  A Library of Spirooxindoles Based on a Stereoselective Three-Component Coupling Reaction

  摘要：

  A collection of structurally complex and chemically diverse small molecules is a useful tool to explore cell circuitry. In this article, we report the split-pool synthesis of more than 3000 spirooxindoles on high capacity macrobeads. The key reaction to assemble the spirooxindole core stereoselectively is a Lewis acid variant of the Williams' three-component coupling, After formation, the skeleton was elaborated using Sonogashira couplings, amide forming reactions, and N-acylations of gamma-lactams. The final library was analyzed by sampling individual macrobeads and by using binomial confidence limits. It was determined that at least 82% of the library compounds should have better than 80% purity. To demonstrate the utility of our discovery process, a high-throughput chemical genetic modifier screen was performed using stock solutions of the resultant products. A number of positives were identified as enhancers of the cellular actions of latrunculin B, an actin polymerization inhibitor. Through resynthesis, we confirmed one of the positives and demonstrated that, in yeast cells, it has an EC50 in the sub-micromolar range.

  DOI：

  10.1021/ja045089d