[(3S,4E)-4-[2-[(1S,2S,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethylspiro[3,4,4a,6,7,8-hexahydro-1H-naphthalene-2,2'-oxirane]-1-yl]ethylidene]-5-oxooxolan-3-yl] 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate | 774581-38-3

• 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: [(3S,4E)-4-[2-[(1S,2S,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethylspiro[3,4,4a,6,7,8-hexahydro-1H-naphthalene-2,2'-oxirane]-1-yl]ethylidene]-5-oxooxolan-3-yl] 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate
• CAS: 774581-38-3
• 化学式: C₂₇H₄₁NO₉
• 分子量: 523.624
• InChiKey: ZZIUQYUBUOBKRL-QVTDAQMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  144
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  丙酸酐 、 [(3S,4E)-4-[2-[(1S,2S,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethylspiro[3,4,4a,6,7,8-hexahydro-1H-naphthalene-2,2'-oxirane]-1-yl]ethylidene]-5-oxooxolan-3-yl] 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate 反应 0.5h， 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：

  穿心莲内酯 在 4-甲基苯磺酸吡啶 、 氯甲酸乙酯 、 溶剂黄146 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 二甲基亚砜 、 苯 为溶剂， 反应 15.25h， 生成 [(3S,4E)-4-[2-[(1S,2S,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethylspiro[3,4,4a,6,7,8-hexahydro-1H-naphthalene-2,2'-oxirane]-1-yl]ethylidene]-5-oxooxolan-3-yl] 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate
  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

文献信息

• Synthesis and structure–activity relationships of andrographolide analogues as novel cytotoxic agents
  作者：Srinivas Nanduri、Vijay Kumar Nyavanandi、Siva Sanjeeva Rao Thunuguntla、Sridevi Kasu、Mahesh Kumar Pallerla、P. Sai Ram、Sriram Rajagopal、R. Ajaya Kumar、Rajagopalan Ramanujam、J. Moses Babu、Krishnamurthi Vyas、A. Sivalakshmi Devi、G. Om Reddy、Venkateswarlu Akella

  DOI：10.1016/j.bmcl.2004.06.090

  日期：2004.9

  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.