(2R,3S)-[(3R,5aS,6R,8aS,9R,10S,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-yl] 3-benzamido-2-hydroxy-3-phenylpropanoate | 1435474-92-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3S)-[(3R,5aS,6R,8aS,9R,10S,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-yl] 3-benzamido-2-hydroxy-3-phenylpropanoate
• 英文别名: [(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl] (2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoate
• CAS: 1435474-92-2
• 化学式: C₃₁H₃₇NO₈
• 分子量: 551.637
• InChiKey: XGQACKGZFHOQDA-QTDBTWEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  dihydroartemisinin 、 N-苯甲酰基-(2R,3S)-3-苯基异丝氨酸 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 以42%的产率得到(2R,3S)-[(3R,5aS,6R,8aS,9R,10S,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-yl] 3-benzamido-2-hydroxy-3-phenylpropanoate
  参考文献：
  名称：

  Design, Synthesis, and Antiplasmodial Activity of Hybrid Compounds Based on (2R,3S)-N-Benzoyl-3-phenylisoserine

  摘要：

  A series of hybrid compounds based, on.(2R,3S)-N-benzoyl-3-phenylisoserine, artemisinin, and quinoline moieties was synthesized and tested for in vitro antiplasmodial activity against erythrocytic stages of K1 and W2 strains of Plasmodium falciparum Two hybrid compounds incorporating (2R,3S)-N-benzoyl-3-phenylisoserine and artemisinin scaffolds were 3- to 4-fold more active than dihydroartemisinin, with nanomolar IC50 values against Plasmodium falciparum K1 strain.

  DOI：

  10.1021/ml400164t

文献信息

• Design, Synthesis, and Antiplasmodial Activity of Hybrid Compounds Based on (2<i>R</i>,3<i>S</i>)-<i>N</i>-Benzoyl-3-phenylisoserine
  作者：Peter M. Njogu、Jiri Gut、Philip J. Rosenthal、Kelly Chibale

  DOI：10.1021/ml400164t

  日期：2013.7.11

  A series of hybrid compounds based, on.(2R,3S)-N-benzoyl-3-phenylisoserine, artemisinin, and quinoline moieties was synthesized and tested for in vitro antiplasmodial activity against erythrocytic stages of K1 and W2 strains of Plasmodium falciparum Two hybrid compounds incorporating (2R,3S)-N-benzoyl-3-phenylisoserine and artemisinin scaffolds were 3- to 4-fold more active than dihydroartemisinin, with nanomolar IC50 values against Plasmodium falciparum K1 strain.