| 1163245-39-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 1163245-39-3
• 化学式: C₂₃H₄₀O₅Si
• 分子量: 424.653
• InChiKey: KJFYDQRKOWSCRU-GIHONLOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  29.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  在 2,6-二甲基吡啶 、 甲醇 、 barium hydroxide octahydrate 、 三乙胺 、 三苯基膦 、 lithium diisopropyl amide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 4.49h， 生成 C₅₄H₁₀₂O₉Si₄
  参考文献：
  名称：

  Amphidinolide B: Total Synthesis, Structural Investigation, and Biological Evaluation

  摘要：

  The total syntheses of amphidinolide B-1 and the proposed structure of amphidinolide B-2 have been accomplished. Key aspects of this work include the development of a practical, non-transitionmetal-mediated method for the construction of the C-13-C-15 diene, the identification of alpha-chelation and dipole minimization models for diastereoselective methyl ketone aldol reactions, the discovery of a spontaneous Horner-Wadsworth-Emmons macrocyclization strategy, and the development of a novel late stage method for construction of an allylic epoxide moiety. The originally proposed structure for amphidinolide B-2 and diastereomers thereof display potent antitumor activities with IC50 values ranging from 3.3 to 94.5 nM against human solid and blood tumor cells. Of the different stereoisomers, the proposed structure of amphidinolide B-2 is over 12-fold more potent than the C-8,C-9-epimer and C-18-epimer in human DU145 prostate cancer cells. These data suggest that the epoxide stereochemistry is a significant factor for anticancer activity.

  DOI：

  10.1021/jo3026077
• 作为产物：
  描述：

  (2R,3S,4R,6R)-2-(4-Methoxy-benzyloxy)-4-methyl-3,6-bis-triethylsilanyloxy-heptanethioic acid S-ethyl ester 在 copper(l) iodide 、 水 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.42h， 生成
  参考文献：
  名称：

  Amphidinolide B: Total Synthesis, Structural Investigation, and Biological Evaluation

  摘要：

  The total syntheses of amphidinolide B-1 and the proposed structure of amphidinolide B-2 have been accomplished. Key aspects of this work include the development of a practical, non-transitionmetal-mediated method for the construction of the C-13-C-15 diene, the identification of alpha-chelation and dipole minimization models for diastereoselective methyl ketone aldol reactions, the discovery of a spontaneous Horner-Wadsworth-Emmons macrocyclization strategy, and the development of a novel late stage method for construction of an allylic epoxide moiety. The originally proposed structure for amphidinolide B-2 and diastereomers thereof display potent antitumor activities with IC50 values ranging from 3.3 to 94.5 nM against human solid and blood tumor cells. Of the different stereoisomers, the proposed structure of amphidinolide B-2 is over 12-fold more potent than the C-8,C-9-epimer and C-18-epimer in human DU145 prostate cancer cells. These data suggest that the epoxide stereochemistry is a significant factor for anticancer activity.

  DOI：

  10.1021/jo3026077

文献信息

• Total Syntheses of Amphidinolides B1, B4, G1, H1 and Structure Revision of Amphidinolide H2
  作者：Alois Fürstner、Laure C. Bouchez、Louis Morency、Jaques-Alexis Funel、Vilnis Liepins、François-Hugues Porée、Ryan Gilmour、Daniel Laurich、Florent Beaufils、Minoru Tamiya

  DOI：10.1002/chem.200802067

  日期：2009.4.14

  unselective “chemist” when it comes to making the highly cytotoxic amphidinolide macrolides of the B/G/H series. To date, 16 different such compounds have been isolated, all of which could now be approached by a highly convergent and largely catalysis‐based route (see figure). This notion is exemplified by the total synthesis of five prototype members of this family.

  在生产具有高细胞毒性的B / G / H系列安非他命类大环内酯类药物时，自然界是一个非选择性的“化学家”。迄今为止，已分离出16种不同的此类化合物，现在可以通过高度聚合且主要基于催化作用的途径来接近所有这些化合物（见图）。该族的五个原型成员的总合成就是这一概念的例证。