dispiro[adamantane-2,2'-[1,3]dioxolane-4',1''-cyclohexane]-5-yl 5-(dimethylamino)naphthalene-1-sulfonate | 1346840-19-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: dispiro[adamantane-2,2'-[1,3]dioxolane-4',1''-cyclohexane]-5-yl 5-(dimethylamino)naphthalene-1-sulfonate
• CAS: 1346840-19-4
• 化学式: C₂₉H₃₇NO₅S
• 分子量: 511.682
• InChiKey: WPRGCEJTFHCVAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  73.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-羟基-2-金刚烷酮 、 丹酰氯 在 吡啶 、 4-二甲氨基吡啶 、 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 dispiro[adamantane-2,2'-[1,3]dioxolane-4',1''-cyclohexane]-5-yl 5-(dimethylamino)naphthalene-1-sulfonate
  参考文献：
  名称：

  Investigating the Antimalarial Action of 1,2,4-Trioxolanes with Fluorescent Chemical Probes

  摘要：

  The 1,2,4-trioxolanes are a new class of synthetic peroxidic antimalarials currently in human clinical trials. The well-known reactivity of the 1,2,4-trioxolane ring toward inorganic ferrous iron and ferrous iron heme is proposed to play a role in the antimalarial action of this class of compounds. We have designed structurally relevant fluorescent chemical probes to study the subcellular localization of 1,2,4-trioxolanes in cultured Plasmodium falciparum parasites. Microscopy experiments revealed that a probe fluorescently labeled on the adamantane ring accumulated specifically in digestive vacuole-associated neutral lipid bodies within the parasite while an isosteric, but nonperoxidic, congener did not. Probes fluorescently labeled on the cyclohexane ring showed no distinct localization pattern. In their subcellular localization and peroxidative effects, 1,2,4-trioxolane probes behave much like artemisinin-based probes studied previously. Our results are consistent with a role for adamantane-derived carbon-centered radicals in the antimalarial action of 1,2,4-trioxolanes, as hypothesized previously on the basis of chemical reactivity studies.

  DOI：

  10.1021/jm2012003

文献信息

• Investigating the Antimalarial Action of 1,2,4-Trioxolanes with Fluorescent Chemical Probes
  作者：Carmony L. Hartwig、Erica M.W. Lauterwasser、Sumit S. Mahajan、Jonathan M. Hoke、Roland A. Cooper、Adam R. Renslo

  DOI：10.1021/jm2012003

  日期：2011.12.8

  The 1,2,4-trioxolanes are a new class of synthetic peroxidic antimalarials currently in human clinical trials. The well-known reactivity of the 1,2,4-trioxolane ring toward inorganic ferrous iron and ferrous iron heme is proposed to play a role in the antimalarial action of this class of compounds. We have designed structurally relevant fluorescent chemical probes to study the subcellular localization of 1,2,4-trioxolanes in cultured Plasmodium falciparum parasites. Microscopy experiments revealed that a probe fluorescently labeled on the adamantane ring accumulated specifically in digestive vacuole-associated neutral lipid bodies within the parasite while an isosteric, but nonperoxidic, congener did not. Probes fluorescently labeled on the cyclohexane ring showed no distinct localization pattern. In their subcellular localization and peroxidative effects, 1,2,4-trioxolane probes behave much like artemisinin-based probes studied previously. Our results are consistent with a role for adamantane-derived carbon-centered radicals in the antimalarial action of 1,2,4-trioxolanes, as hypothesized previously on the basis of chemical reactivity studies.