9-[9-(β-carboline-9-yl)nonyl]-β-carboline | 1225056-71-2

• 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: 9-[9-(β-carboline-9-yl)nonyl]-β-carboline
• 英文别名: 9-[9-(beta-Carboline-9-yl)nonyl]-beta-carboline；9-(9-pyrido[3,4-b]indol-9-ylnonyl)pyrido[3,4-b]indole
• CAS: 1225056-71-2
• 化学式: C₃₁H₃₂N₄
• 分子量: 460.622
• InChiKey: JJAATQLWMKLMJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-[9-(β-carboline-9-yl)nonyl]-β-carboline 、 碘甲烷 以 丙酮 为溶剂， 反应 24.0h， 以98%的产率得到2-methyl-9-[9-(2-methyl-β-carboline-9-yl)nonyl]-β-carboline-2-ium diiodide
  参考文献：
  名称：

  Bivalent β-Carbolines as Potential Multitarget Anti-Alzheimer Agents

  摘要：

  Alzheimer's disease (AD) is a prevalent neurodegenerative disorder with multifactorial causes that requires multitargeted treatment. Inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) improve cholinergic signaling in the central nervous system and thus AChE inhibitors are well established in the therapy of AD to improve memory disturbances and other cognitive symptoms. On the other hand, AD patients benefit from reduction of pathologic glutamate-induced, Ca2+-mediated excitotoxicity by the N-methyl-D-aspartate receptor (NR) antagonist memantine. New drugs that simultaneously affect both cholinergic transmission and glutamate-induced excitotoxicity may further improve AD treatment. While connecting beta-carboline units by alkylene spacers in two different series of compounds and subsequent evaluation of their AChE/BChE-inhibitory potential, we found that several of these bivalent beta-carbolines were potent NR blockers. The most promising compound was a N-9-homobivalent beta-carboline with a nonylene spacer, which displayed IC50 values of 0.5 nM for AChE, 5.7 nM for BChE, and 1.4 mu M for NR, respectively.

  DOI：

  10.1021/jm1000024
• 作为产物：
  描述：

  色胺 在 palladium 10% on activated carbon 、 sodium hydride 、 溶剂黄146 作用下， 以 甲醇 、 5,5-dimethyl-1,3-cyclohexadiene 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 9-[9-(β-carboline-9-yl)nonyl]-β-carboline
  参考文献：
  名称：

  季铵化去甲哈尔满二聚体、其药物组合物及抗菌用途

  摘要：

  本发明涉及抗菌剂领域，具体涉及季铵化去甲哈尔满二聚体、其药物组合物及抗菌用途。本发明提供了一种季铵化去甲哈尔满二聚体，抗MRSA的MIC值在0.015～0.5μg/mL，强于临床一线用药万古霉素，可用于治疗MRSA引起的感染性疾病如菌血症、肺炎、心肌炎、伤口感染、骨关节感染等。季铵化去甲哈尔满二聚体同时对革兰氏阴性菌大肠杆菌、肺炎克雷伯菌和鲍曼不动杆菌具有活性，具有广谱性抗菌特征。

  公开号：

  CN118530258A

文献信息

• Bivalent β-Carbolines as Potential Multitarget Anti-Alzheimer Agents
  作者：Yvonne Rook、Kai-Uwe Schmidtke、Friedemann Gaube、Dirk Schepmann、Bernhard Wünsch、Jörg Heilmann、Jochen Lehmann、Thomas Winckler

  DOI：10.1021/jm1000024

  日期：2010.5.13

  Alzheimer's disease (AD) is a prevalent neurodegenerative disorder with multifactorial causes that requires multitargeted treatment. Inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) improve cholinergic signaling in the central nervous system and thus AChE inhibitors are well established in the therapy of AD to improve memory disturbances and other cognitive symptoms. On the other hand, AD patients benefit from reduction of pathologic glutamate-induced, Ca2+-mediated excitotoxicity by the N-methyl-D-aspartate receptor (NR) antagonist memantine. New drugs that simultaneously affect both cholinergic transmission and glutamate-induced excitotoxicity may further improve AD treatment. While connecting beta-carboline units by alkylene spacers in two different series of compounds and subsequent evaluation of their AChE/BChE-inhibitory potential, we found that several of these bivalent beta-carbolines were potent NR blockers. The most promising compound was a N-9-homobivalent beta-carboline with a nonylene spacer, which displayed IC50 values of 0.5 nM for AChE, 5.7 nM for BChE, and 1.4 mu M for NR, respectively.
• Evaluation of Homobivalent Carbolines as Designed Multiple Ligands for the Treatment of Neurodegenerative Disorders
  作者：Robert Otto、Robert Penzis、Friedemann Gaube、Oliver Adolph、Karl J. Föhr、Paul Warncke、Dina Robaa、Dorothea Appenroth、Christian Fleck、Christoph Enzensperger、Jochen Lehmann、Thomas Winckler

  DOI：10.1021/acs.jmedchem.5b00958

  日期：2015.8.27

  Neurodegenerative diseases represent a challenge for biomedical research due to their high prevalence and lack of mechanism-based treatments. Because of the complex pathology of neurodegenerative disorders, multifunctional drugs have been increasingly recognized as potential treatments. We identified homobivalent gamma-carbolinium salts as potent inihitors of both cholinesterases, N-methyl-D-aspartate receptors, and monoamine oxidases. Homobivalent gamma-carbolines displayed similar structure activity relationships on all tested targets and may present promising designed multiple ligands for the treatment of neurodegenerative disorders.