4-{[(3aR,5S,7aR)-3a-hydroxy-7a-methyl-1-oxooctahydro-1H-inden-5-yl]oxy}-4-oxobutanoic acid | 874986-75-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-{[(3aR,5S,7aR)-3a-hydroxy-7a-methyl-1-oxooctahydro-1H-inden-5-yl]oxy}-4-oxobutanoic acid
• CAS: 874986-75-1
• 化学式: C₁₄H₂₀O₆
• 分子量: 284.309
• InChiKey: DLAVOXGZZWNRAE-QCZZGDTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.05
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  100.9
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-{[(3aR,5S,7aR)-3a-hydroxy-7a-methyl-1-oxooctahydro-1H-inden-5-yl]oxy}-4-oxobutanoic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 Succinic acid (S)-2-((S)-4-amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethyl ester (3aR,5S,7aR)-3a-hydroxy-7a-methyl-1-oxo-octahydro-inden-5-yl ester
  参考文献：
  名称：

  Design of potent inhibitors for Schistosoma japonica glutathione S-transferase

  摘要：

  We implemented both structure-based drug design and the concept of polyvalency to discover a series of potent and unsymmetrical Schistosoma japonicum glutathione S-transferase (SjGST) inhibitors 10-12. This strategy achieved not only an excellent enhancement (10- to 490-fold) in the inhibitory potency, compared to the monofunctional analogues 1-5, but was also an effective modification by selecting a hydrophobic moiety with a flexible linker. The designed compounds with a low micromolar hit demonstrate special values in refining the new generation of SjGST inhibitors. The stoichiometry of the binding is one inhibitor molecule per SjGST monomer via isothermal titration calorimetric measurement. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.077
• 作为产物：
  描述：

  (3aR,5S,7aR)-3a,5-dihydroxy-7a-methyloctahydro-(1H)-inden-1-one 、 丁二酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以85%的产率得到4-{[(3aR,5S,7aR)-3a-hydroxy-7a-methyl-1-oxooctahydro-1H-inden-5-yl]oxy}-4-oxobutanoic acid
  参考文献：
  名称：

  Design of potent inhibitors for Schistosoma japonica glutathione S-transferase

  摘要：

  We implemented both structure-based drug design and the concept of polyvalency to discover a series of potent and unsymmetrical Schistosoma japonicum glutathione S-transferase (SjGST) inhibitors 10-12. This strategy achieved not only an excellent enhancement (10- to 490-fold) in the inhibitory potency, compared to the monofunctional analogues 1-5, but was also an effective modification by selecting a hydrophobic moiety with a flexible linker. The designed compounds with a low micromolar hit demonstrate special values in refining the new generation of SjGST inhibitors. The stoichiometry of the binding is one inhibitor molecule per SjGST monomer via isothermal titration calorimetric measurement. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.077