gomphostenin

• 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: gomphostenin
• 英文别名: GN；3-[2-((1S,2R,4aS,8aS)-2-hydroxymethyl-1,4a,5-trimethyl-7-oxo-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl)-ethyl]-5H-furan-2-one；3-[2-(2-hydroxymethyl-1,4a,5-trimethyl-7-oxo-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl)-ethyl]-5H-furan-2-one；4-[2-[(1S,2R,4aS,8aS)-2-(hydroxymethyl)-1,4a,5-trimethyl-7-oxo-3,4,8,8a-tetrahydro-2H-naphthalen-1-yl]ethyl]-2H-furan-5-one
• 化学式: C₂₀H₂₈O₄
• 分子量: 332.44
• InChiKey: TUKIEDUNYYIEJB-JQERWDHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  gomphostenin 、 1-溴-三氟对二甲苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以55%的产率得到4-[2-[(1S,2R,4aS,8aS)-1,4a,5-trimethyl-7-oxo-2-[[4-(trifluoromethyl)phenyl]methoxymethyl]-3,4,8,8a-tetrahydro-2H-naphthalen-1-yl]ethyl]-2H-furan-5-one
  参考文献：
  名称：

  In vitro and in vivo antimalarial evaluation of semi-synthetic derivatives of gomphostenin

  摘要：

  A novel series of semi-synthetic gomphostenin derivatives (1-9) were prepared utilizing C-14 hydroxyl group for the first time and studied for their antimalarial properties. In vitro antiplasmodial activity was evaluated against both the chloroquine sensitive and resistant strains of Plasmodium falciparum. Most of the compounds exhibited superior or comparable antiplasmodial activity compared to parent compound, that is, gomphostenin (GN). Based upon in vitro antiplasmodial activity, compounds with IC(50) values less than 10 mu M were selected for in vivo antiplasmodial evaluation against Plasmodium berghei infection in mice model. GN derivatives 3 and 5 were found to have curative activity with moderate chemosuppression of 65% and 69%, respectively, at the dose level of 150 mg/kg/day. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.035

文献信息

• In vitro and in vivo antimalarial evaluation of semi-synthetic derivatives of gomphostenin
  作者：Manisha Sathe、M.P. Kaushik

  DOI：10.1016/j.bmcl.2010.05.035

  日期：2010.7

  A novel series of semi-synthetic gomphostenin derivatives (1-9) were prepared utilizing C-14 hydroxyl group for the first time and studied for their antimalarial properties. In vitro antiplasmodial activity was evaluated against both the chloroquine sensitive and resistant strains of Plasmodium falciparum. Most of the compounds exhibited superior or comparable antiplasmodial activity compared to parent compound, that is, gomphostenin (GN). Based upon in vitro antiplasmodial activity, compounds with IC(50) values less than 10 mu M were selected for in vivo antiplasmodial evaluation against Plasmodium berghei infection in mice model. GN derivatives 3 and 5 were found to have curative activity with moderate chemosuppression of 65% and 69%, respectively, at the dose level of 150 mg/kg/day. (C) 2010 Elsevier Ltd. All rights reserved.