20-ethoxymethoxytriptophenolide methylether | 1603837-05-3

• 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: 20-ethoxymethoxytriptophenolide methylether
• 英文别名: (3bS,9bR)-9b-(ethoxymethoxymethyl)-6-methoxy-7-propan-2-yl-3,3b,4,5,10,11-hexahydronaphtho[2,1-e][2]benzofuran-1-one
• CAS: 1603837-05-3
• 化学式: C₂₄H₃₂O₅
• 分子量: 400.515
• InChiKey: IZYNDPRFNCMJPR-URXFXBBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  20-ethoxymethoxytriptophenolide methylether 在 sodium periodate 、 ammonium cerium (IV) nitrate 、 cerium(III) chloride heptahydrate 、 三溴化硼 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 3.33h， 生成 (5aR,9aR,10aS,11aS)-5a-(hydroxymethyl)-8-isopropyl-4,5,5a,10a,11,11a-hexahydro-1H-oxireno[2',3':8a,9]phenanthro[1,2-c]furan-3,9-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of 20-hydroxytriptonide and its analogues

  摘要：

  20-Hydroxytriptonide was synthesized from readily accessible L-abietic acid in 22 linear steps, which features a Barton reaction carried out under air atmosphere to install the C20-hydroxy group. Meanwhile, we also synthesized (5R)-5-hydroxytriptolide's probable metabolite product. Preliminary structure activity relationship studies revealed that C20-angular methyl group might play a key role in maintaining the electronic properties of the whole molecule, which was essential for retaining the cytotoxic activity and might easily and inevitably be affected by the introduction of a new group. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.070
• 作为产物：
  描述：

  在 正丁基锂 、 2,6-二叔丁基-4-甲基苯酚 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 20-ethoxymethoxytriptophenolide methylether
  参考文献：
  名称：

  Synthesis and biological evaluation of 20-hydroxytriptonide and its analogues

  摘要：

  20-Hydroxytriptonide was synthesized from readily accessible L-abietic acid in 22 linear steps, which features a Barton reaction carried out under air atmosphere to install the C20-hydroxy group. Meanwhile, we also synthesized (5R)-5-hydroxytriptolide's probable metabolite product. Preliminary structure activity relationship studies revealed that C20-angular methyl group might play a key role in maintaining the electronic properties of the whole molecule, which was essential for retaining the cytotoxic activity and might easily and inevitably be affected by the introduction of a new group. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.070

文献信息

• Synthesis and biological evaluation of 20-hydroxytriptonide and its analogues
  作者：Hongtao Xu、Huanyu Tang、Zhuo Yang、Huijin Feng、Yuanchao Li

  DOI：10.1016/j.tet.2014.03.070

  日期：2014.5

  20-Hydroxytriptonide was synthesized from readily accessible L-abietic acid in 22 linear steps, which features a Barton reaction carried out under air atmosphere to install the C20-hydroxy group. Meanwhile, we also synthesized (5R)-5-hydroxytriptolide's probable metabolite product. Preliminary structure activity relationship studies revealed that C20-angular methyl group might play a key role in maintaining the electronic properties of the whole molecule, which was essential for retaining the cytotoxic activity and might easily and inevitably be affected by the introduction of a new group. (C) 2014 Elsevier Ltd. All rights reserved.