6-chloro-N-decyl-1,2,3,4-tetrahydroacridin-9-amine | 1440519-87-8

• 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: 6-chloro-N-decyl-1,2,3,4-tetrahydroacridin-9-amine
• CAS: 1440519-87-8
• 化学式: C₂₃H₃₃ClN₂
• 分子量: 372.981
• InChiKey: LYTYXSPDNBKVMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  6,9-二氯-1,2,3,4-四氢吖啶 、 1-氨基癸烷 以 戊醇 为溶剂， 反应 48.0h， 以55%的产率得到6-chloro-N-decyl-1,2,3,4-tetrahydroacridin-9-amine
  参考文献：
  名称：

  Investigation of the role of linker moieties in bifunctional tacrine hybrids

  摘要：

  Alzheimer's disease (AD) is a complex neurological disorder with multiple inter-connected factors playing roles in the onset and progression of the disease. One strategy currently being explored for the development of new therapeutics for AD involves linking tacrine, a known acetylcholinesterase (AChE) inhibitor, to another drug to create bifunctional hybrids. The role and influence on activity of the linker moiety in these hybrids remains ill-defined. In this study, three series of 6-chlorotacrine with linkers varying in terminal functional group and length were synthesized, evaluated for AChE inhibition, and compared to tacrine and 6-chlorotacrine-mefenamic acid hybrids. Out of the compounds with terminal amine, methyl, and hydroxyl moieties tested, several highly potent molecules (low nanomolar IC50 values) comprised of linkers with terminal amines were identified. These 6-chlorotacrine with linkers were significantly more potent than tacrine alone and were often more potent than similar 6-chlorotacrine-mefenamic acid hybrids. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.047

文献信息

• Investigation of the role of linker moieties in bifunctional tacrine hybrids
  作者：Todd J. Eckroat、Keith D. Green、Rebecca A. Reed、Joshua J. Bornstein、Sylvie Garneau-Tsodikova

  DOI：10.1016/j.bmc.2013.02.047

  日期：2013.6

  Alzheimer's disease (AD) is a complex neurological disorder with multiple inter-connected factors playing roles in the onset and progression of the disease. One strategy currently being explored for the development of new therapeutics for AD involves linking tacrine, a known acetylcholinesterase (AChE) inhibitor, to another drug to create bifunctional hybrids. The role and influence on activity of the linker moiety in these hybrids remains ill-defined. In this study, three series of 6-chlorotacrine with linkers varying in terminal functional group and length were synthesized, evaluated for AChE inhibition, and compared to tacrine and 6-chlorotacrine-mefenamic acid hybrids. Out of the compounds with terminal amine, methyl, and hydroxyl moieties tested, several highly potent molecules (low nanomolar IC50 values) comprised of linkers with terminal amines were identified. These 6-chlorotacrine with linkers were significantly more potent than tacrine alone and were often more potent than similar 6-chlorotacrine-mefenamic acid hybrids. (C) 2013 Elsevier Ltd. All rights reserved.