cis-3,3''-(2,2''-(1-methylpiperidine-2,6-diyl)bis(ethane-2,1-diyl))bis(1H-indole) fumaric acid | 1236194-84-5

• 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: cis-3,3''-(2,2''-(1-methylpiperidine-2,6-diyl)bis(ethane-2,1-diyl))bis(1H-indole) fumaric acid
• 英文别名: 3-[2-[(2S,6R)-6-[2-(1H-indol-3-yl)ethyl]-1-methylpiperidin-2-yl]ethyl]-1H-indole
• CAS: 1236194-84-5
• 化学式: C₂₆H₃₁N₃
• 分子量: 385.552
• InChiKey: CJQDQTGQDJURBL-SZPZYZBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  34.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,6-bis(2-(1H-indol-3-yl)vinyl)-1-methylpyridin-1-ium 4-methylbenzenesulfonate 在 1% Pd/C 、 氢气 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以18%的产率得到cis-3,3''-(2,2''-(1-methylpiperidine-2,6-diyl)bis(ethane-2,1-diyl))bis(1H-indole) fumaric acid
  参考文献：
  名称：

  Quinlobelane: A water-soluble lobelane analogue and inhibitor of VMAT2

  摘要：

  Replacing the phenyl groups in the structure of the VMAT2 inhibitor, lobelane with either pyridyl, quinolyl or indolyl groups affords novel analogues with improved water solubility. The synthetic methodologies reported herein also underscore the paucity of hydrogenation methods that offer selectivity in the synthesis of the different classes of heteroaromatic lobelane analogues. The quinolyl group was the only replacement for the phenyl group in lobelane that retained VMAT2 inhibition. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.04.117

文献信息

• Quinlobelane: A water-soluble lobelane analogue and inhibitor of VMAT2
  作者：Ashish P. Vartak、A. Gabriela Deaciuc、Linda P. Dwoskin、Peter A. Crooks

  DOI：10.1016/j.bmcl.2010.04.117

  日期：2010.6

  Replacing the phenyl groups in the structure of the VMAT2 inhibitor, lobelane with either pyridyl, quinolyl or indolyl groups affords novel analogues with improved water solubility. The synthetic methodologies reported herein also underscore the paucity of hydrogenation methods that offer selectivity in the synthesis of the different classes of heteroaromatic lobelane analogues. The quinolyl group was the only replacement for the phenyl group in lobelane that retained VMAT2 inhibition. (C) 2010 Elsevier Ltd. All rights reserved.