tert-butyl (2S,3R)-2-(3-(7-bromo-6-chloro-4-oxoquinazolin-3(4H)-yl)-2-oxopropyl)-3-(((2R,3aS,4R,7R,7aS)-7,8,8-trimethyloctahydro-4,7-methanobenzofuran-2-yl)oxy)piperidine-1-carboxylate | 948888-19-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: tert-butyl (2S,3R)-2-(3-(7-bromo-6-chloro-4-oxoquinazolin-3(4H)-yl)-2-oxopropyl)-3-(((2R,3aS,4R,7R,7aS)-7,8,8-trimethyloctahydro-4,7-methanobenzofuran-2-yl)oxy)piperidine-1-carboxylate
• CAS: 948888-19-5
• 化学式: C₃₃H₄₃BrClN₃O₆
• 分子量: 693.078
• InChiKey: WESKKJKTDJFWFO-XQHLFEMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.74
• 重原子数：
  44.0
• 可旋转键数：
  6.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  99.96
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,3R)-2-(3-(7-bromo-6-chloro-4-oxoquinazolin-3(4H)-yl)-2-oxopropyl)-3-(((2R,3aS,4R,7R,7aS)-7,8,8-trimethyloctahydro-4,7-methanobenzofuran-2-yl)oxy)piperidine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以41%的产率得到(2S,3R)-halofuginone
  参考文献：
  名称：

  (2R,3S)-(+)- and (2S,3R)-(−)-Halofuginone lactate: Synthesis, absolute configuration, and activity against Cryptosporidium parvum

  摘要：

  The trans-enantiomers of the commercially important anti-protozoal compound Halofuginone have been prepared and characterized, and the absolute configuration was assigned by X-ray crystallography. The activity of both enantiomers against Cryptosporidium parvum was determined in vitro and related to acute toxicity in vivo. It was shown that both the activity and the toxicity are properties of the (2R,3S)-enantiomer. We conclude that with respect to broadening the therapeutic window there is no advantage in application of one enantiomer over the application of the racemic mixture in the treatment of C parvum infections. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.053
• 作为产物：
  描述：

  (+)-欧沃豪斯邻位羟基内醚®二聚物 、 tert-butyl trans-2-(3-(7-bromo-6-chloro-4-oxoquinazolin-3(4H)-yl)-2-oxopropyl)-3-hydroxypiperidine-1-carboxylate 在 对甲苯磺酸 作用下， 以 氯仿 为溶剂， 反应 72.0h， 以16%的产率得到tert-butyl (2R,3S)-2-(3-(7-bromo-6-chloro-4-oxoquinazolin-3(4H)-yl)-2-oxopropyl)-3-(((2R,3aS,4R,7R,7aS)-7,8,8-trimethyloctahydro-4,7-methanobenzofuran-2-yl)oxy)piperidine-1-carboxylate
  参考文献：
  名称：

  (2R,3S)-(+)- and (2S,3R)-(−)-Halofuginone lactate: Synthesis, absolute configuration, and activity against Cryptosporidium parvum

  摘要：

  The trans-enantiomers of the commercially important anti-protozoal compound Halofuginone have been prepared and characterized, and the absolute configuration was assigned by X-ray crystallography. The activity of both enantiomers against Cryptosporidium parvum was determined in vitro and related to acute toxicity in vivo. It was shown that both the activity and the toxicity are properties of the (2R,3S)-enantiomer. We conclude that with respect to broadening the therapeutic window there is no advantage in application of one enantiomer over the application of the racemic mixture in the treatment of C parvum infections. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.053