Manadoperoxide A | 1233532-07-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: Manadoperoxide A
• 英文别名: methyl 2-[(3S,4S,6R)-6-methoxy-4-methyl-6-[(4E,6E)-6-methylocta-4,6-dienyl]dioxan-3-yl]acetate
• CAS: 1233532-07-4
• 化学式: C₁₈H₃₀O₅
• 分子量: 326.433
• InChiKey: SXYZFCRIZKWROR-FGLSIJRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 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：

  Manadoperoxide A 在 溶剂黄146 、 锌 作用下， 以 乙醚 为溶剂， 反应 24.0h， 生成 methyl (3S,4S,10E,12E)-3-hydroxy-4,12-dimethyl-6-oxotetradeca-10,12-dienoate
  参考文献：
  名称：

  Manadoperoxides A−D from the Indonesian Sponge Plakortis cfr. simplex. Further Insights on the Structure−Activity Relationships of Simple 1,2-Dioxane Antimalarials

  摘要：

  The new endoperoxyketal polyketides manadoperoxides A-D (2-5) have been isolated from he Indonesian sponge Plakartis cfr. simplex and their stereostructures established by means of spectroscopic data and semisynthetic transformations. Manadoperoxides were assayed in vitro against D10 and W2 strains of Plasmodium falciparum and showed moderate antimalarial activity compared to that of plakortin (1) and peroxyplakoric B(3) ester (9), the latter differing from manadoperoxide 13 only by minor structural details. This unexpected difference in the antimalarial activity has been rationalized on the basis of our recently published model for the interaction of 1,2-dioximes with heme and production of C-centered radicals toxic to the parasite. For the manadoperoxides, either the endoperoxide linkage is inaccessible to the heme iron or the O1 radical cannot evolve to produce a C-centered radical.

  DOI：

  10.1021/np100196b