(+/-)-(8S*,10R*,21R*)-21-hydroxy-7,9,11-trioxatetraspiro[5.1.1.1.5(12).2(10).3.(8).2.(6)]tetracosa-1,4,13,16-dien-3,15-one | 1052171-63-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-(8S*,10R*,21R*)-21-hydroxy-7,9,11-trioxatetraspiro[5.1.1.1.5(12).2(10).3.(8).2.(6)]tetracosa-1,4,13,16-dien-3,15-one
• CAS: 1052171-63-7
• 化学式: C₂₁H₂₂O₆
• 分子量: 370.402
• InChiKey: BWUOKXCUQDTZQU-ZHPFXUNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.04
• 重原子数：
  27.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  82.06
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-(1-hydroxytridecylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione 、 (+/-)-(8S*,10R*,21R*)-21-hydroxy-7,9,11-trioxatetraspiro[5.1.1.1.5(12).2(10).3.(8).2.(6)]tetracosa-1,4,13,16-dien-3,15-one 以 四氢呋喃 为溶剂， 反应 6.0h， 以36%的产率得到(+/-)-(8S*,10R*,21R*)-3-oxahexadecanoic acid 7,9,11-trioxatetraspiro[5.1.1.1.5(12).2(10).3.(8).2.(6)]tetracosa-1,4,13,16-dien-3,15-on-21-yl ester
  参考文献：
  名称：

  Enhanced Antimalarial Activity of Novel Synthetic Aculeatin Derivatives

  摘要：

  We report the design, synthesis, and in vitro evaluation of novel polyspirocyclic structures, inspired by the antimalarial natural products, the aculeatins. A divergent synthetic strategy was conceived for the practical supply and has allowed the discovery of two novel and more potent analogues active on the Plasmodium falciparum 3D7 strain. Moreover, these compounds proved to be potent against Toxoplasma gondii. A number Of features that govern these inhibitions were identified.

  DOI：

  10.1021/jm8007322
• 作为产物：
  描述：

  (+/-)-5-hydroxy-1-(4-hydroxyphenyl)-6-{2-[2-(4-hydroxyphenyl)ethyl]-[1,3]-dithian-2-yl}hexan-3-one 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 水 、 丙酮 为溶剂， 反应 16.0h， 以19%的产率得到(+/-)-(8S*,10R*,21R*)-21-hydroxy-7,9,11-trioxatetraspiro[5.1.1.1.5(12).2(10).3.(8).2.(6)]tetracosa-1,4,13,16-dien-3,15-one
  参考文献：
  名称：

  Enhanced Antimalarial Activity of Novel Synthetic Aculeatin Derivatives

  摘要：

  We report the design, synthesis, and in vitro evaluation of novel polyspirocyclic structures, inspired by the antimalarial natural products, the aculeatins. A divergent synthetic strategy was conceived for the practical supply and has allowed the discovery of two novel and more potent analogues active on the Plasmodium falciparum 3D7 strain. Moreover, these compounds proved to be potent against Toxoplasma gondii. A number Of features that govern these inhibitions were identified.

  DOI：

  10.1021/jm8007322

文献信息

• Enhanced Antimalarial Activity of Novel Synthetic Aculeatin Derivatives
  作者：Marine Peuchmaur、Nadia Saïdani、Cyrille Botté、Eric Maréchal、Henri Vial、Yung-Sing Wong

  DOI：10.1021/jm8007322

  日期：2008.8.1

  We report the design, synthesis, and in vitro evaluation of novel polyspirocyclic structures, inspired by the antimalarial natural products, the aculeatins. A divergent synthetic strategy was conceived for the practical supply and has allowed the discovery of two novel and more potent analogues active on the Plasmodium falciparum 3D7 strain. Moreover, these compounds proved to be potent against Toxoplasma gondii. A number Of features that govern these inhibitions were identified.