(+)-N,N’-bis[(7R,11R)-3-chloro-6,7,10,11-tetrahydro-9-methyl-7,11-methanocicloocta[b]quinolin-12-yl]-1,4-phenylenedimethanamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (+)-N,N’-bis[(7R,11R)-3-chloro-6,7,10,11-tetrahydro-9-methyl-7,11-methanocicloocta[b]quinolin-12-yl]-1,4-phenylenedimethanamine
• 英文别名: (1R,13R)-7-chloro-N-[[4-[[[(1R,13R)-7-chloro-15-methyl-10-azatetracyclo[11.3.1.02,11.04,9]heptadeca-2,4(9),5,7,10,14-hexaen-3-yl]amino]methyl]phenyl]methyl]-15-methyl-10-azatetracyclo[11.3.1.02,11.04,9]heptadeca-2,4(9),5,7,10,14-hexaen-3-amine
• 化学式: C₄₂H₄₀Cl₂N₄
• 分子量: 671.712
• InChiKey: ASENLOWIVRYAAI-XAZDILKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  48
• 可旋转键数：
  6
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-N,N’-bis[(7R,11R)-3-chloro-6,7,10,11-tetrahydro-9-methyl-7,11-methanocicloocta[b]quinolin-12-yl]-1,4-phenylenedimethanamine 在 盐酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以16 mg的产率得到(+)-N,N’-bis[(7R,11R)-3-chloro-6,7,10,11-tetrahydro-9-methyl-7,11-methanocicloocta[b]quinolin-12-yl]-1,4-phenylenedimethanamine bis(hydrochloride)
  参考文献：
  名称：

  Synthesis and antiprotozoal activity of oligomethylene- and p-phenylene-bis(methylene)-linked bis(+)-huprines

  摘要：

  We have synthesized a series of dimers of (+)-(7R, 11R)-huprine Y and evaluated their activity against Trypanosoma brucei, Plasmodium falciparum, rat myoblast L6 cells and human acetylcholinesterase (hAChE), and their brain permeability. Most dimers have more potent and selective trypanocidal activity than huprine Y and are brain permeable, but they are devoid of antimalarial activity and remain active against hAChE. Lead optimization will focus on identifying compounds with a more favourable trypanocidal/ anticholinesterase activity ratio. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.025
• 作为产物：
  描述：

  1,4-对二氯苄 、 (+)-huprine Y 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 74.0h， 生成 (+)-N,N’-bis[(7R,11R)-3-chloro-6,7,10,11-tetrahydro-9-methyl-7,11-methanocicloocta[b]quinolin-12-yl]-1,4-phenylenedimethanamine 、 (+)-N-[(7R,11R)-3-chloro-6,7,10,11-tetrahydro-9-methyl-7,11-methanocicloocta[b]quinolin-12-yl]-[4-(chloromethyl)phenyl]methanamine
  参考文献：
  名称：

  Synthesis and antiprotozoal activity of oligomethylene- and p-phenylene-bis(methylene)-linked bis(+)-huprines

  摘要：

  We have synthesized a series of dimers of (+)-(7R, 11R)-huprine Y and evaluated their activity against Trypanosoma brucei, Plasmodium falciparum, rat myoblast L6 cells and human acetylcholinesterase (hAChE), and their brain permeability. Most dimers have more potent and selective trypanocidal activity than huprine Y and are brain permeable, but they are devoid of antimalarial activity and remain active against hAChE. Lead optimization will focus on identifying compounds with a more favourable trypanocidal/ anticholinesterase activity ratio. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.025

文献信息

• Synthesis and antiprotozoal activity of oligomethylene- and p-phenylene-bis(methylene)-linked bis(+)-huprines
  作者：Irene Sola、Albert Artigas、Martin C. Taylor、Stephen Y. Gbedema、Belén Pérez、M. Victòria Clos、Colin W. Wright、John M. Kelly、Diego Muñoz-Torrero

  DOI：10.1016/j.bmcl.2014.10.025

  日期：2014.12

  We have synthesized a series of dimers of (+)-(7R, 11R)-huprine Y and evaluated their activity against Trypanosoma brucei, Plasmodium falciparum, rat myoblast L6 cells and human acetylcholinesterase (hAChE), and their brain permeability. Most dimers have more potent and selective trypanocidal activity than huprine Y and are brain permeable, but they are devoid of antimalarial activity and remain active against hAChE. Lead optimization will focus on identifying compounds with a more favourable trypanocidal/ anticholinesterase activity ratio. (C) 2014 Elsevier Ltd. All rights reserved.