9-[(9-bromononyl)amino]-1,2,3,4-tetrahydroacridine | 1356151-48-8

• 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: 9-[(9-bromononyl)amino]-1,2,3,4-tetrahydroacridine
• 英文别名: N-(9-bromononyl)-1,2,3,4-tetrahydroacridin-9-amine
• CAS: 1356151-48-8
• 化学式: C₂₂H₃₁BrN₂
• 分子量: 403.406
• InChiKey: CXVFQMGQSCJTRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-[(9-bromononyl)amino]-1,2,3,4-tetrahydroacridine 在 氢溴酸 作用下， 以 甲醇 、 水 为溶剂， 以160 mg的产率得到9-[(9-bromononyl)amino]-1,2,3,4-tetrahydroacridine hydrobromide
  参考文献：
  名称：

  Huprine-他克林异二聚体作为抗淀粉样蛋白的化合物，可能对阿尔茨海默氏症和Pri病毒病具有重要意义

  摘要：

  已经开发了一个胡珀林-他克林异二聚体家族，可以同时阻断乙酰胆碱酯酶（AChE）的活性位点和周围位点。它们与AChE的双重位点结合，得到动力学和分子模型研究的支持，导致高度有效地抑制人AChE的催化活性，更重要的是，在体外中和了AChE对两者聚集的病理伴侣作用β-淀粉样肽（Aβ）和a蛋白肽在the蛋白的聚集中起关键作用。Huprine-Tacrine异二聚体具有附加价值，因为它们在体外对人的丁酰胆碱酯酶，自身诱导的Aβ聚集和β-分泌酶显示出有效的抑制活性。最后，他们能够穿越血脑屏障，如在人工膜模型试验中预测的那样，并在OF1小鼠的离体实验中得到证实，达到了它们在中枢神经系统中的多个生物学靶标。总体而言，这些化合物是用于治疗阿尔茨海默氏病和病毒疾病的有前途的先导化合物。

  DOI：

  10.1021/jm200840c
• 作为产物：
  描述：

  环己酮 在 potassium hydroxide 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 51.0h， 生成 9-[(9-bromononyl)amino]-1,2,3,4-tetrahydroacridine
  参考文献：
  名称：

  Inhibition of cholinesterase and monoamine oxidase-B activity by Tacrine–Homoisoflavonoid hybrids

  摘要：

  A series of Tacrine-Homoisoflavonoid hybrids were designed, synthesised and evaluated as inhibitors of cholinesterases (ChEs) and human monoamine oxidases (MAOs). Most of the compounds were found to be potent against both ChEs and MAO-B. Among these hybrids, compound 8b, with a 6 carbon linker between tacrine and (E)-7-hydroxy-3-(4-methoxybenzylidene)chroman-4-one, proved to be the most potent against AChE and MAO-B with IC50 values of 67.9 nM and 0.401 mu M, respectively. This compound was observed to cross the blood-brain barrier (BBB) in a parallel artificial membrane permeation assay for the BBB (PAMPA-BBB). The results indicated that compound 8b is an excellent multifunctional promising compound for development of novel drugs for Alzheimer's disease (AD). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.09.050

文献信息

• Inhibition of cholinesterase and monoamine oxidase-B activity by Tacrine–Homoisoflavonoid hybrids
  作者：Yang Sun、Jianwen Chen、Xuemin Chen、Ling Huang、Xingshu Li

  DOI：10.1016/j.bmc.2013.09.050

  日期：2013.12

  A series of Tacrine-Homoisoflavonoid hybrids were designed, synthesised and evaluated as inhibitors of cholinesterases (ChEs) and human monoamine oxidases (MAOs). Most of the compounds were found to be potent against both ChEs and MAO-B. Among these hybrids, compound 8b, with a 6 carbon linker between tacrine and (E)-7-hydroxy-3-(4-methoxybenzylidene)chroman-4-one, proved to be the most potent against AChE and MAO-B with IC50 values of 67.9 nM and 0.401 mu M, respectively. This compound was observed to cross the blood-brain barrier (BBB) in a parallel artificial membrane permeation assay for the BBB (PAMPA-BBB). The results indicated that compound 8b is an excellent multifunctional promising compound for development of novel drugs for Alzheimer's disease (AD). (C) 2013 Elsevier Ltd. All rights reserved.
• Huprine–Tacrine Heterodimers as Anti-Amyloidogenic Compounds of Potential Interest against Alzheimer’s and Prion Diseases
  作者：Carles Galdeano、Elisabet Viayna、Irene Sola、Xavier Formosa、Pelayo Camps、Albert Badia、M. Victòria Clos、Júlia Relat、Míriam Ratia、Manuela Bartolini、Francesca Mancini、Vincenza Andrisano、Mario Salmona、Cristina Minguillón、Gema C. González-Muñoz、M. Isabel Rodríguez-Franco、Axel Bidon-Chanal、F. Javier Luque、Diego Muñoz-Torrero

  DOI：10.1021/jm200840c

  日期：2012.1.26

  in an artificial membrane model assay and demonstrated in ex vivo experiments with OF1 mice, reaching their multiple biological targets in the central nervous system. Overall, these compounds are promising lead compounds for the treatment of Alzheimer’s and prion diseases.

  已经开发了一个胡珀林-他克林异二聚体家族，可以同时阻断乙酰胆碱酯酶（AChE）的活性位点和周围位点。它们与AChE的双重位点结合，得到动力学和分子模型研究的支持，导致高度有效地抑制人AChE的催化活性，更重要的是，在体外中和了AChE对两者聚集的病理伴侣作用β-淀粉样肽（Aβ）和a蛋白肽在the蛋白的聚集中起关键作用。Huprine-Tacrine异二聚体具有附加价值，因为它们在体外对人的丁酰胆碱酯酶，自身诱导的Aβ聚集和β-分泌酶显示出有效的抑制活性。最后，他们能够穿越血脑屏障，如在人工膜模型试验中预测的那样，并在OF1小鼠的离体实验中得到证实，达到了它们在中枢神经系统中的多个生物学靶标。总体而言，这些化合物是用于治疗阿尔茨海默氏病和病毒疾病的有前途的先导化合物。