(6S,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,7-dimethyl-2,3,12,12a-tetrahydropyrazino[1',2':1,6] pyrido[3,4-b]indole-1,4(6H,7H)dione | 1370438-55-3

• 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
• 英文名称: (6S,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,7-dimethyl-2,3,12,12a-tetrahydropyrazino[1',2':1,6] pyrido[3,4-b]indole-1,4(6H,7H)dione
• 英文别名: NEU-0000257；(2S,8R)-2-(1,3-benzodioxol-5-yl)-6,17-dimethyl-3,6,17-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),11,13,15-tetraene-4,7-dione
• CAS: 1370438-55-3
• 化学式: C₂₃H₂₁N₃O₄
• 分子量: 403.437
• InChiKey: UMVKZCLEGWYPLH-UTKZUKDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  64
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl 1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 mineral oil 为溶剂， 反应 3.58h， 生成 (6S,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,7-dimethyl-2,3,12,12a-tetrahydropyrazino[1',2':1,6] pyrido[3,4-b]indole-1,4(6H,7H)dione
  参考文献：
  名称：

  Synthesis and evaluation of human phosphodiesterases (PDE) 5 inhibitor analogs as trypanosomal PDE inhibitors. Part 2. Tadalafil analogs

  摘要：

  In this Letter we describe our ongoing target repurposing efforts focused on discovery of inhibitors of the essential trypanosomal phosphodiesterase TbrPDEB1. This enzyme has been implicated in virulence of Trypanosoma brucei, the causative agent of human African trypanosomiasis (HAT). We outline the synthesis and biological evaluation of analogs of tadalafil, a human PDE5 inhibitor currently utilized for treatment of erectile dysfunction, and report that these analogs are weak inhibitors of TbrPDEB1. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.118

文献信息

• Synthesis and evaluation of human phosphodiesterases (PDE) 5 inhibitor analogs as trypanosomal PDE inhibitors. Part 2. Tadalafil analogs
  作者：Stefan O. Ochiana、Alden Gustafson、Nicholas D. Bland、Cuihua Wang、Michael J. Russo、Robert K. Campbell、Michael P. Pollastri

  DOI：10.1016/j.bmcl.2012.01.118

  日期：2012.4

  In this Letter we describe our ongoing target repurposing efforts focused on discovery of inhibitors of the essential trypanosomal phosphodiesterase TbrPDEB1. This enzyme has been implicated in virulence of Trypanosoma brucei, the causative agent of human African trypanosomiasis (HAT). We outline the synthesis and biological evaluation of analogs of tadalafil, a human PDE5 inhibitor currently utilized for treatment of erectile dysfunction, and report that these analogs are weak inhibitors of TbrPDEB1. (C) 2012 Elsevier Ltd. All rights reserved.