(1R,3S,5R,6R,7R,8S)-8-hydroxy-3-(methoxymethoxy)-13,14,15-trimethylenedecahydroazuleno[6,7-β]furan-12-one

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,3S,5R,6R,7R,8S)-8-hydroxy-3-(methoxymethoxy)-13,14,15-trimethylenedecahydroazuleno[6,7-β]furan-12-one
• 化学式: C₁₇H₂₂O₅
• 分子量: 306.359
• InChiKey: VUMXWAMNMBBOTL-OSLXHZNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.59
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1R,3S,5R,6R,7R,8S)-8-hydroxy-3-(methoxymethoxy)-13,14,15-trimethylenedecahydroazuleno[6,7-β]furan-12-one 在 4-甲基苯磺酸吡啶 作用下， 以 叔丁醇 为溶剂， 反应 28.0h， 以68%的产率得到4,8-二羟基-3,6,9-三亚甲基-3a,4,5,6a,7,8,9a,9b-八氢薁并[5,4-d]呋喃-2-酮
  参考文献：
  名称：

  Antitrypanosomal structure–activity-relationship study of synthetic cynaropicrin derivatives

  摘要：

  Cynaropicrin is a guaianolide sesquiterpene lactone with a 5-7-5 tricyclic skeleton, four exo-olefins, and two hydroxyl groups. Recently, it was found that the compound is a potent in vitro and in vivo inhibitor of the protozoan parasite Trypanosoma brucei, which causes human African trypanosomiasis (HAT; sleeping sickness). In this Letter, chemical derivatization of cynaropicrin and the structure-activity-relationship (SAR) study against T. brucei is described. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.099
• 作为产物：
  描述：

  (1R,3S,5R,6R,7R,8S)-3-(methoxymethoxy)-13,14,15-trimethylene-12-oxododecahydroazuleno[6,7-β]furan-4-yl 17-((methoxymethoxy)methyl)acrylate 在 水 、 sodium hydroxide 作用下， 反应 28.0h， 以84%的产率得到(1R,3S,5R,6R,7R,8S)-8-hydroxy-3-(methoxymethoxy)-13,14,15-trimethylenedecahydroazuleno[6,7-β]furan-12-one
  参考文献：
  名称：

  Antitrypanosomal structure–activity-relationship study of synthetic cynaropicrin derivatives

  摘要：

  Cynaropicrin is a guaianolide sesquiterpene lactone with a 5-7-5 tricyclic skeleton, four exo-olefins, and two hydroxyl groups. Recently, it was found that the compound is a potent in vitro and in vivo inhibitor of the protozoan parasite Trypanosoma brucei, which causes human African trypanosomiasis (HAT; sleeping sickness). In this Letter, chemical derivatization of cynaropicrin and the structure-activity-relationship (SAR) study against T. brucei is described. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.099

文献信息

• Synthesis of cynaropicrin- d 4
  作者：Takuya Sato、Shihori Hara、Makiko Sato、Keita Ogawa、Michael Adams、Toyonobu Usuki

  DOI：10.1016/j.bmcl.2015.10.065

  日期：2015.12

  Cynaropicrin is a guaianolide sesquiterpene lactone, which has potent in vitro and in vivo inhibitory activity against Trypanosoma brucei, the protozoan parasite that causes human African trypanosomiasis (HAT; sleeping sickness). Herein, we describe the synthesis of cynaropicrin's deuterated derivative, cynaropicrin-d(4), by the replacement of the side chain of natural cynaropicrin. The synthesized cynaropicrin-d(4) could be employed as an internal standard for liquid chromatography-mass spectrometry (LC-MS) analysis, in the pharmacokinetic study of cynaropicrin. This could potentially advance the study of this therapeutic lead. (C) 2015 Elsevier Ltd. All rights reserved.
• Antitrypanosomal structure–activity-relationship study of synthetic cynaropicrin derivatives
  作者：Toyonobu Usuki、Makiko Sato、Shihori Hara、Yukiko Yoshimoto、Ryosuke Kondo、Stefanie Zimmermann、Marcel Kaiser、Reto Brun、Matthias Hamburger、Michael Adams

  DOI：10.1016/j.bmcl.2013.12.099

  日期：2014.2

  Cynaropicrin is a guaianolide sesquiterpene lactone with a 5-7-5 tricyclic skeleton, four exo-olefins, and two hydroxyl groups. Recently, it was found that the compound is a potent in vitro and in vivo inhibitor of the protozoan parasite Trypanosoma brucei, which causes human African trypanosomiasis (HAT; sleeping sickness). In this Letter, chemical derivatization of cynaropicrin and the structure-activity-relationship (SAR) study against T. brucei is described. (C) 2013 Elsevier Ltd. All rights reserved.