(S,E)-4-hydroxy-3-(2-((1S,2S,4aS,5R,6R,8aR)-6-hydroxy-5,8a-dimethyl-5-((trityloxy)methyl)octahydro-1H-spiro[naphthalene-2,2'-oxiran]-1-yl)ethylidene)dihydrofuran-2(3H)-one | 774581-30-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (S,E)-4-hydroxy-3-(2-((1S,2S,4aS,5R,6R,8aR)-6-hydroxy-5,8a-dimethyl-5-((trityloxy)methyl)octahydro-1H-spiro[naphthalene-2,2'-oxiran]-1-yl)ethylidene)dihydrofuran-2(3H)-one
• CAS: 774581-30-5
• 化学式: C₃₉H₄₄O₆
• 分子量: 608.775
• InChiKey: AWUWGGBQLXWUCM-UHQCIXIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.19
• 重原子数：
  45.0
• 可旋转键数：
  8.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  88.52
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S,E)-4-hydroxy-3-(2-((1S,2S,4aS,5R,6R,8aR)-6-hydroxy-5,8a-dimethyl-5-((trityloxy)methyl)octahydro-1H-spiro[naphthalene-2,2'-oxiran]-1-yl)ethylidene)dihydrofuran-2(3H)-one 在 甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 [(1R,2R,4aR,5S,6S,8aS)-1-(hydroxymethyl)-5-[(2E)-2-[(4S)-4-hydroxy-2-oxooxolan-3-ylidene]ethyl]-1,4a-dimethylspiro[3,4,5,7,8,8a-hexahydro-2H-naphthalene-6,2'-oxirane]-2-yl] 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
• 作为产物：
  描述：

  三苯基氯甲烷 在 吡啶 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 (S,E)-4-hydroxy-3-(2-((1S,2S,4aS,5R,6R,8aR)-6-hydroxy-5,8a-dimethyl-5-((trityloxy)methyl)octahydro-1H-spiro[naphthalene-2,2'-oxiran]-1-yl)ethylidene)dihydrofuran-2(3H)-one
  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