(S,E)-5-oxo-4-(2-((4aR,6aR,7S,8S,10aS,10bR)-3,3,6a,10b-tetramethyloctahydro-1H,6H-spiro[naphtho[2,1-d][1,3]dioxine-8,2'-oxiran]-7-yl)ethylidene)tetrahydrofuran-3-yl (tert-butoxycarbonyl)glycinate | 848125-64-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S,E)-5-oxo-4-(2-((4aR,6aR,7S,8S,10aS,10bR)-3,3,6a,10b-tetramethyloctahydro-1H,6H-spiro[naphtho[2,1-d][1,3]dioxine-8,2'-oxiran]-7-yl)ethylidene)tetrahydrofuran-3-yl (tert-butoxycarbonyl)glycinate
• CAS: 848125-64-4
• 化学式: C₃₀H₄₅NO₉
• 分子量: 563.689
• InChiKey: XISVOJVNTHLORT-MVSTVAQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  40.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  121.92
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (S,E)-5-oxo-4-(2-((4aR,6aR,7S,8S,10aS,10bR)-3,3,6a,10b-tetramethyloctahydro-1H,6H-spiro[naphtho[2,1-d][1,3]dioxine-8,2'-oxiran]-7-yl)ethylidene)tetrahydrofuran-3-yl (tert-butoxycarbonyl)glycinate 在 溶剂黄146 作用下， 反应 0.75h， 生成 [(1R,2R,4aR,5S,6S,8aS)-1,4a-dimethyl-5-[(2E)-2-[(4S)-4-[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]oxy-2-oxooxolan-3-ylidene]ethyl]-2-propanoyloxyspiro[3,4,5,7,8,8a-hexahydro-2H-naphthalene-6,2'-oxirane]-1-yl]methyl propanoate
  参考文献：
  名称：

  Synthesis and structure–activity relationships of andrographolide analogues as novel cytotoxic agents

  摘要：

  Andrographolide 1, the cytotoxic agent of the plant Androgrophis paniculata was subjected to semi-synthetic studies leading to the preparation of a number of potent and novel analogues. Of the analogues synthesized, while 8,17-epoxy andrographolide 6 retained the cytotoxic activity of 1, ester derivatives of 6 exhibited considerable improvement in activity. Lower activity was observed when the epoxy moiety in the triacetate 9, derived from 6 was modified. Synthesis and structure-activity relationships are discussed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.090
• 作为产物：
  描述：

  (S,E)-4-hydroxy-3-(2-((1S,2S,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyloctahydro-1H-spiro [naphthalene-2,2'-oxirane]-1-yl)ethylidene)dihydrofuran-2(3H)-one 在 4-甲基苯磺酸吡啶 、 氯甲酸乙酯 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 、 苯 为溶剂， 反应 9.0h， 生成 (S,E)-5-oxo-4-(2-((4aR,6aR,7S,8S,10aS,10bR)-3,3,6a,10b-tetramethyloctahydro-1H,6H-spiro[naphtho[2,1-d][1,3]dioxine-8,2'-oxiran]-7-yl)ethylidene)tetrahydrofuran-3-yl (tert-butoxycarbonyl)glycinate
  参考文献：
  名称：

  Synthesis and structure–activity relationships of andrographolide analogues as novel cytotoxic agents

  摘要：

  Andrographolide 1, the cytotoxic agent of the plant Androgrophis paniculata was subjected to semi-synthetic studies leading to the preparation of a number of potent and novel analogues. Of the analogues synthesized, while 8,17-epoxy andrographolide 6 retained the cytotoxic activity of 1, ester derivatives of 6 exhibited considerable improvement in activity. Lower activity was observed when the epoxy moiety in the triacetate 9, derived from 6 was modified. Synthesis and structure-activity relationships are discussed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.090