(1R,2R,3S,3aR,8bS)-6-[[(2S,3R,6R)-6-[(1S)-1,2-dihydroxyethyl]-3-methoxy-1,4-dioxan-2-yl]oxy]-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-N-prop-2-ynyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide | 1426430-10-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (1R,2R,3S,3aR,8bS)-6-[[(2S,3R,6R)-6-[(1S)-1,2-dihydroxyethyl]-3-methoxy-1,4-dioxan-2-yl]oxy]-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-N-prop-2-ynyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide
• CAS: 1426430-10-5
• 化学式: C₃₆H₃₉NO₁₂
• 分子量: 677.705
• InChiKey: HOERYQXMPSYULD-IZFLLGIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  49
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  175
• 氢给体数：
  5
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (1R,2R,3S,3aR,8bS)-6-[[(2S,3R,6R)-6-[(1S)-1,2-dihydroxyethyl]-3-methoxy-1,4-dioxan-2-yl]oxy]-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-N-prop-2-ynyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide 在 copper(II) sulfate 、 sodium ascorbate 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 48.0h， 以86%的产率得到(1R,2R,3S,3aR,8bS)-N-[[1-[3-[2-[2-[3-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]propoxy]ethoxy]ethoxy]propyl]triazol-4-yl]methyl]-6-[[(2S,3R,6R)-6-[(1S)-1,2-dihydroxyethyl]-3-methoxy-1,4-dioxan-2-yl]oxy]-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide
  参考文献：
  名称：

  Synthesis of Biotinylated Episilvestrol: Highly Selective Targeting of the Translation Factors eIF4AI/II

  摘要：

  Silvestrol (1) and episilvestrol (2) are protein synthesis inhibitors, and the former has shown efficacy in multiple mouse models of cancer; however, the selectivity of these potent cytotoxic natural products has not been described. Herein, it is demonstrated that eukaryotic initiation factors eIF4AI/II were the only proteins detected to bind silvestrol (1) and biotinylated episilvestrol (9) by affinity purification. Our study demonstrates the remarkable selectivity of these promising chemotherapeutics.

  DOI：

  10.1021/ol400401d
• 作为产物：
  描述：

  5MYC-UTR-LUC抑制剂(EPISILVESTROL) 在 水 、 N,N'-二环己基碳二亚胺 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 50.58h， 生成 (1R,2R,3S,3aR,8bS)-6-[[(2S,3R,6R)-6-[(1S)-1,2-dihydroxyethyl]-3-methoxy-1,4-dioxan-2-yl]oxy]-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-N-prop-2-ynyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide
  参考文献：
  名称：

  Synthesis of Biotinylated Episilvestrol: Highly Selective Targeting of the Translation Factors eIF4AI/II

  摘要：

  Silvestrol (1) and episilvestrol (2) are protein synthesis inhibitors, and the former has shown efficacy in multiple mouse models of cancer; however, the selectivity of these potent cytotoxic natural products has not been described. Herein, it is demonstrated that eukaryotic initiation factors eIF4AI/II were the only proteins detected to bind silvestrol (1) and biotinylated episilvestrol (9) by affinity purification. Our study demonstrates the remarkable selectivity of these promising chemotherapeutics.

  DOI：

  10.1021/ol400401d