2-[(2-adamantyl)carbonyl]-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one | 1228602-43-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 2-[(2-adamantyl)carbonyl]-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one
• 英文别名: 2-(adamantane-2-carbonyl)-3,6,7,11b-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4-one
• CAS: 1228602-43-4
• 化学式: C₂₃H₂₈N₂O₂
• 分子量: 364.488
• InChiKey: QRJMKXCBHSPSCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-金刚烷甲酸 、 1,2,3,6,7,11B-六氢-4H-吡嗪并[2,1-Alpha]异喹啉-4-酮 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以74%的产率得到2-[(2-adamantyl)carbonyl]-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one
  参考文献：
  名称：

  Praziquantel analogs with activity against juvenile Schistosoma mansoni

  摘要：

  Six amide and four urea derivatives of praziquantel were synthesized and tested for antischistosomal activity against juvenile and adults stages of Schistosoma mansoni in infected mice. Only one of these had significant activity against adult worms, but, unlike praziquantel, six of these had low to modest activity against juvenile worms. A praziquantel ketone derivative had the best combination of activity against juveniles and adults, but it had no effect on the motility of adult S. mansoni in ex vivo culture. Cytochrome P450 metabolic stability data support the hypothesis that the major trans-cyclohexanol metabolite of praziquantel plays an important role in the antischistosomal activity of this drug. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.03.001

文献信息

• Praziquantel analogs with activity against juvenile Schistosoma mansoni
  作者：Yuxiang Dong、Jacques Chollet、Mireille Vargas、Nuha R. Mansour、Quentin Bickle、Yazen Alnouti、Jiangeng Huang、Jennifer Keiser、Jonathan L. Vennerstrom

  DOI：10.1016/j.bmcl.2010.03.001

  日期：2010.4

  Six amide and four urea derivatives of praziquantel were synthesized and tested for antischistosomal activity against juvenile and adults stages of Schistosoma mansoni in infected mice. Only one of these had significant activity against adult worms, but, unlike praziquantel, six of these had low to modest activity against juvenile worms. A praziquantel ketone derivative had the best combination of activity against juveniles and adults, but it had no effect on the motility of adult S. mansoni in ex vivo culture. Cytochrome P450 metabolic stability data support the hypothesis that the major trans-cyclohexanol metabolite of praziquantel plays an important role in the antischistosomal activity of this drug. (C) 2010 Elsevier Ltd. All rights reserved.