N-去甲基ent-他达拉非 | 929100-66-3

• 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
• 中文名称: N-去甲基ent-他达拉非
• 中文别名: 他达拉非杂质29
• 英文名称: (6R,12aS)-6-(benzo[d][1,3]dioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione
• 英文别名: (6R,12aS)-6-benzo[1,3]dioxol-5-yl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione；(6R,12aS)-N-Desmethyl ent-Tadalafil；(2R,8S)-2-(1,3-benzodioxol-5-yl)-3,6,17-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),11,13,15-tetraene-4,7-dione
• CAS: 929100-66-3
• 化学式: C₂₁H₁₇N₃O₄
• 分子量: 375.384
• InChiKey: XHDLVMPUSXRZOS-MGPUTAFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  83.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-去甲基ent-他达拉非 、 碘苯 在 potassium phosphate 、 copper(l) iodide 、 (1S,2S)-(+)-1,2-环己二胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 336.0h， 以46%的产率得到(6R,12aS)-6-benzo[1,3]dioxol-5-yl-2-phenyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione
  参考文献：
  名称：

  PDE5 inhibitors: An original access to novel potent arylated analogues of tadalafil

  摘要：

  A method to access totally new analogues of tadalafil was explored, The Buchwald reaction was adapted and used to replace the methyl group of tadalafit by various aryl groups. Inhibition potencies on PDE5 of these analogues were determined and proved to be comparable to the one of tadalafil. Using the same route, compounds with the same level of activity but improved water solubility were produced by introducing a pyridine or a pyrimidine ring. This original route also opens access to new unpatented compounds. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.069
• 作为产物：
  描述：

  L-色氨酸甲酯盐酸盐 在 氨 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 44.0h， 生成 N-去甲基ent-他达拉非
  参考文献：
  名称：

  PDE5 inhibitors: An original access to novel potent arylated analogues of tadalafil

  摘要：

  A method to access totally new analogues of tadalafil was explored, The Buchwald reaction was adapted and used to replace the methyl group of tadalafit by various aryl groups. Inhibition potencies on PDE5 of these analogues were determined and proved to be comparable to the one of tadalafil. Using the same route, compounds with the same level of activity but improved water solubility were produced by introducing a pyridine or a pyrimidine ring. This original route also opens access to new unpatented compounds. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.069

文献信息

• PDE5 inhibitors: An original access to novel potent arylated analogues of tadalafil
  作者：Terence Beghyn、Candide Hounsou、Benoit P. Deprez

  DOI：10.1016/j.bmcl.2006.10.069

  日期：2007.2

  A method to access totally new analogues of tadalafil was explored, The Buchwald reaction was adapted and used to replace the methyl group of tadalafit by various aryl groups. Inhibition potencies on PDE5 of these analogues were determined and proved to be comparable to the one of tadalafil. Using the same route, compounds with the same level of activity but improved water solubility were produced by introducing a pyridine or a pyrimidine ring. This original route also opens access to new unpatented compounds. (c) 2006 Elsevier Ltd. All rights reserved.