12-benzyl-2-(cyclohexylacetyl)-1,2,3,4,6,7,12,12b-octahydropyrazino[2,1-a]β-carboline-3,4-dione | 1357104-38-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 12-benzyl-2-(cyclohexylacetyl)-1,2,3,4,6,7,12,12b-octahydropyrazino[2,1-a]β-carboline-3,4-dione
• 英文别名: 17-Benzyl-4-(2-cyclohexylacetyl)-4,7,17-triazatetracyclo[8.7.0.02,7.011,16]heptadeca-1(10),11,13,15-tetraene-5,6-dione
• CAS: 1357104-38-1
• 化学式: C₂₉H₃₁N₃O₃
• 分子量: 469.583
• InChiKey: CMDMDVJESQTDPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4,9-二氢-3H-吡啶并(3,4-B)吲哚 在 吡啶 、 氢气 、 三乙胺 、 三氟乙酸 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 39.75h， 生成 12-benzyl-2-(cyclohexylacetyl)-1,2,3,4,6,7,12,12b-octahydropyrazino[2,1-a]β-carboline-3,4-dione
  参考文献：
  名称：

  Synthesis of new praziquantel analogues: Potential candidates for the treatment of schistosomiasis

  摘要：

  An efficient synthesis of antischistosomal drug praziquantel and analogues was achieved and the synthetic route designed was to afford structurally diverse analogues for better structure-activity relationship understanding. Total of nineteen PZQ analogues with structural variations at amide, piperazine and aromatic moieties have been synthesized and fully characterized. Among all the new analogues tested for antischistosomal activity, one dimethoxy tetrahydroisoquinoline analogue and two tetrahydro-beta-carboline analogues exhibited moderate activity against adult Schistosoma mansoni. Tetrahydro-beta-carboline analogues showed moderate activity whereas the presence of p-trifluoromethylbenzoyl and p-toluenesulphonyl moieties resulted in complete suppression of antischistosomal activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.108

文献信息

• Synthesis of new praziquantel analogues: Potential candidates for the treatment of schistosomiasis
  作者：Partha Sarathi Sadhu、Singam Naveen Kumar、Malapaka Chandrasekharam、Livia Pica-Mattoccia、Donato Cioli、Vaidya Jayathirtha Rao

  DOI：10.1016/j.bmcl.2011.11.108

  日期：2012.1

  An efficient synthesis of antischistosomal drug praziquantel and analogues was achieved and the synthetic route designed was to afford structurally diverse analogues for better structure-activity relationship understanding. Total of nineteen PZQ analogues with structural variations at amide, piperazine and aromatic moieties have been synthesized and fully characterized. Among all the new analogues tested for antischistosomal activity, one dimethoxy tetrahydroisoquinoline analogue and two tetrahydro-beta-carboline analogues exhibited moderate activity against adult Schistosoma mansoni. Tetrahydro-beta-carboline analogues showed moderate activity whereas the presence of p-trifluoromethylbenzoyl and p-toluenesulphonyl moieties resulted in complete suppression of antischistosomal activity. (C) 2011 Elsevier Ltd. All rights reserved.