[(1S,3S,7S,8S,11S,12S,14S,15R,16R)-15-[(2S,3R,6R)-3-acetyloxy-6-methyl-5-methylidene-7-[3-[3-[(2-methylpropan-2-yl)oxycarbonyl-[4-[(2-methylpropan-2-yl)oxycarbonyl-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]amino]butyl]amino]propyl]-2,5-dioxoimidazolidin-1-yl]-4-oxoheptan-2-yl]-7,12,16-trimethyl-6-oxo-14-pentacyclo[9.7.0.01,3.03,8.012,16]octadec-4-enyl] acetate | 1356964-39-0

• 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: [(1S,3S,7S,8S,11S,12S,14S,15R,16R)-15-[(2S,3R,6R)-3-acetyloxy-6-methyl-5-methylidene-7-[3-[3-[(2-methylpropan-2-yl)oxycarbonyl-[4-[(2-methylpropan-2-yl)oxycarbonyl-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]amino]butyl]amino]propyl]-2,5-dioxoimidazolidin-1-yl]-4-oxoheptan-2-yl]-7,12,16-trimethyl-6-oxo-14-pentacyclo[9.7.0.01,3.03,8.012,16]octadec-4-enyl] acetate
• CAS: 1356964-39-0
• 化学式: C₆₂H₉₇N₅O₁₄
• 分子量: 1136.48
• InChiKey: SYYROQYXNBGJAF-UYTWSYRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  81
• 可旋转键数：
  30
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  225
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  、 neoboutomellerone 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以12%的产率得到[(1S,3S,7S,8S,11S,12S,14S,15R,16R)-15-[(2S,3R,6R)-3-acetyloxy-6-methyl-5-methylidene-7-[3-[3-[(2-methylpropan-2-yl)oxycarbonyl-[4-[(2-methylpropan-2-yl)oxycarbonyl-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]amino]butyl]amino]propyl]-2,5-dioxoimidazolidin-1-yl]-4-oxoheptan-2-yl]-7,12,16-trimethyl-6-oxo-14-pentacyclo[9.7.0.01,3.03,8.012,16]octadec-4-enyl] acetate
  参考文献：
  名称：

  Semisynthetic neoboutomellerone derivatives as ubiquitin-proteasome pathway inhibitors

  摘要：

  The interesting pharmacological properties of neoboutomellerones 1 and 2 were the basis for the assembly of a small library of analogues consisting of natural products isolated from the plant Neoboutonia melleri and of semisynthetic derivatives. As the two enone systems (C23-C24a and C1-C3) and the two hydroxyls groups (C22 and C26) of neoboutomellerones are required for activity, modifications were focused on these functional groups. Biological evaluation by using a cellular assay for proteasome activity provided clues regarding the mechanism of action of these natural products and synthetic derivatives. Certain neoboutomellerone derivatives inhibited the proliferation of human WM-266-4 melanoma tumor cells at submicromolar concentration and warrant evaluation as anticancer agents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.066

文献信息

• Semisynthetic neoboutomellerone derivatives as ubiquitin-proteasome pathway inhibitors
  作者：Joséphine Beck、Yves Guminski、Christophe Long、Laurence Marcourt、Fadila Derguini、Fabien Plisson、Antonio Grondin、Isabelle Vandenberghe、Stéphane Vispé、Viviane Brel、Yannick Aussagues、Frédéric Ausseil、Paola B. Arimondo、Georges Massiot、François Sautel、Frédéric Cantagrel

  DOI：10.1016/j.bmc.2011.11.066

  日期：2012.1

  The interesting pharmacological properties of neoboutomellerones 1 and 2 were the basis for the assembly of a small library of analogues consisting of natural products isolated from the plant Neoboutonia melleri and of semisynthetic derivatives. As the two enone systems (C23-C24a and C1-C3) and the two hydroxyls groups (C22 and C26) of neoboutomellerones are required for activity, modifications were focused on these functional groups. Biological evaluation by using a cellular assay for proteasome activity provided clues regarding the mechanism of action of these natural products and synthetic derivatives. Certain neoboutomellerone derivatives inhibited the proliferation of human WM-266-4 melanoma tumor cells at submicromolar concentration and warrant evaluation as anticancer agents. (C) 2011 Elsevier Ltd. All rights reserved.