(2R,3R,3aS,6S,6aS,8S,9R,9aR,9bR)-2-ethoxy-8-[(4-methoxybenzyl)oxy]-3,6,9-trimethyl-2,3,6a,7,8,9,9a,9b-octahydro-6H-3a,6-epidioxyazuleno[4,5-b]furan | 1254986-36-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R,3aS,6S,6aS,8S,9R,9aR,9bR)-2-ethoxy-8-[(4-methoxybenzyl)oxy]-3,6,9-trimethyl-2,3,6a,7,8,9,9a,9b-octahydro-6H-3a,6-epidioxyazuleno[4,5-b]furan
• 英文别名: (1S,2R,3R,5R,6R,7R,8S,10S,11S)-3-ethoxy-8-[(4-methoxyphenyl)methoxy]-2,7,11-trimethyl-4,12,13-trioxatetracyclo[9.2.2.01,5.06,10]pentadec-14-ene
• CAS: 1254986-36-1
• 化学式: C₂₅H₃₄O₆
• 分子量: 430.541
• InChiKey: DPAZQDMHDAGMAM-WVZBVPNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  乙醇 、 (3R,3aS,6S,6aS,8S,9R,9aR,9bR)-8-[(4-methoxybenzyl)oxy]-3,6,9-trimethyl-2,3,6a,7,8,9,9a,9b-octahydro-6H-3a,6-epidioxyazuleno[4,5-b]furan-2-ol 在 三氟化硼乙醚 作用下， 以 苯 为溶剂， 以42%的产率得到(2R,3R,3aS,6S,6aS,8S,9R,9aR,9bR)-2-ethoxy-8-[(4-methoxybenzyl)oxy]-3,6,9-trimethyl-2,3,6a,7,8,9,9a,9b-octahydro-6H-3a,6-epidioxyazuleno[4,5-b]furan
  参考文献：
  名称：

  Design, Synthesis, and Development of Novel Guaianolide-Endoperoxides as Potential Antimalarial Agents

  摘要：

  Design and synthesis of a guaianolide-endoperoxide (thaperoxide) 3 was pursued as a new antimalarial lead which was found to be noncytotoxic as compared to the natural product lead thapsigargin 2. Several analogues of 3 were successfully synthesized and found to be comparable to derivatives of artemisinin 1 in in vitro antimalarial assay. Among the synthesized compounds, 22 showed excellent in vitro potency against the cultured parasites (W2 IC50 = 13 nM) without apparent cytotoxicity. Furthermore, SAR trends in thaperoxide analogues are presented and explained with the help of docking studies in the homology model of PfSERCA(PfATP6).

  DOI：

  10.1021/jm1006462