(1R,3S,5R,6R,7R,8S)-3-(methoxymethoxy)-13,14,15-trimethylene-12-oxododecahydroazuleno[6,7-β]furan-8-yl methacrylate | 1549718-98-0

• 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)-3-(methoxymethoxy)-13,14,15-trimethylene-12-oxododecahydroazuleno[6,7-β]furan-8-yl methacrylate
• 英文别名: [(3aR,4S,6aR,8S,9aR,9bR)-8-(methoxymethoxy)-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-methylprop-2-enoate
• CAS: 1549718-98-0
• 化学式: C₂₁H₂₆O₆
• 分子量: 374.434
• InChiKey: OCXFPZTWNSGLNS-XREYTECCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1R,3S,5R,6R,7R,8S)-3-(methoxymethoxy)-13,14,15-trimethylene-12-oxododecahydroazuleno[6,7-β]furan-8-yl methacrylate 在 4-甲基苯磺酸吡啶 作用下， 以 叔丁醇 为溶剂， 反应 26.0h， 以89%的产率得到[(3aR,6abeta,9abeta,9balpha)-十二氢-8alpha-羟基-3,6,9-三(亚甲基)-2-氧代薁并[4,5-b]呋喃-4beta-基]甲基丙烯酸酯
  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 2,4,6-三氯苯甲酰氯 、 水 、 三乙胺 、 sodium hydroxide 作用下， 以 甲苯 为溶剂， 反应 36.0h， 生成 (1R,3S,5R,6R,7R,8S)-3-(methoxymethoxy)-13,14,15-trimethylene-12-oxododecahydroazuleno[6,7-β]furan-8-yl methacrylate
  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

• 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.