9-octylamino-1,2,3,4-tetrahydroacridine

• 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-octylamino-1,2,3,4-tetrahydroacridine
• 英文别名: N-octyl-1,2,3,4-tetrahydroacridin-9-amine
• 化学式: C₂₁H₃₀N₂
• 分子量: 310.483
• InChiKey: YBNDUUUQKSTMNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 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-octylamino-1,2,3,4-tetrahydroacridine 、 4-甲氧基苯甲醛 、 联苯甲酰 在 indium(III) chloride 、 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 96.0h， 以74%的产率得到N-[8-[2-(4-methoxyphenyl)-4,5-diphenylimidazol-1-yl]octyl]-1,2,3,4-tetrahydroacridin-9-amine
  参考文献：
  名称：

  通过一锅四组分反应合成他克林-丝氨酸杂种，并作为乙酰胆碱酯酶和丁酰胆碱酯酶抑制剂进行生物学评估

  摘要：

  合成了一系列新的他克林-丝氨酸杂种，并测试了它们在纳摩尔浓度范围内以IC 50抑制乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BuChE）的能力。关键步骤是使用InCl 3作为最佳催化剂，使9-氨基烷基氨基-1,2,3,4-四氢ac啶，苄基，不同取代的芳族醛与NH 4 OAc进行一锅四组分缩合反应。发现他克林-丝氨酸杂种是胆碱酯酶的有效和选择性抑制剂。作为四组分方法向四取代咪唑的扩展，针对AChE和BuChE测试了一系列新的双-（2,4,5-三苯基-1 H-咪唑）或双（n）-卵磷脂。

  DOI：

  10.1016/j.ejmech.2013.01.029
• 作为产物：
  描述：

  2-(cyclohex-1-enylamino)benzoic acid 在 三氯氧磷 、 苯酚 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 9-octylamino-1,2,3,4-tetrahydroacridine
  参考文献：
  名称：

  Search of antitubercular activities in tetrahydroacridines: Synthesis and biological evaluation

  摘要：

  A series of 9-substituted tetrahydroacridines were synthesized by nucleophilic substitution of chloro group with different nucleophiles in 9-chlorotetrahydroacridine (2). The latter could be obtained by POCl3 mediated cyclization of the intermediate enamine, which in turn, was prepared by acid catalyzed condensation of anthranilic acid and cyclohexanone. Most of the compounds on antitubercular evaluation against M. tuberculosis H37 Rv and H37 Ra strains exhibited potent activities with MIC 6.125-0.78 mu g/mL comparable to the standard drugs. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.025

文献信息

• [EN] IMPROVING POSTSYNAPTIC RESPONSE BY A COMBINATION OF 4-MINOPYRIDINE AND AGONIST<br/>[FR] REPONSE POSTSYNAPTIQUE AMELIOREE PAR UNE COMBINAISON DE 4-AMINOPYRIDINE ET AGONISTE
  申请人：US GOV HEALTH & HUMAN SERV

  公开号：WO2002072025A2

  公开（公告）日：2002-09-19

  A method for improving postsynaptic neurotransmission comprises administering a 4-AP agent in combination with a postsynaptic agonist to prolong and potentiate agonist-induced postsynaptic elevation of intracellular Ca2+ levels as compared to the levels in the absence of the 4-AP agent.
• Synthesis of tacrine-lophine hybrids via one-pot four component reaction and biological evaluation as acetyl- and butyrylcholinesterase inhibitors
  作者：Jessie Sobieski da Costa、João Paulo Bizarro Lopes、Dennis Russowsky、Cesar Liberato Petzhold、Antonio César de Amorim Borges、Marco Antonio Ceschi、Eduardo Konrath、Cristiane Batassini、Paula Santana Lunardi、Carlos Alberto Saraiva Gonçalves

  DOI：10.1016/j.ejmech.2013.01.029

  日期：2013.4

  A novel series of tacrine-lophine hybrids was synthesized and tested for their ability to inhibit acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) with IC50 in the nanomolar concentration scale. The key step is the one-pot four component condensation reaction of 9-aminoalkylamino-1,2,3,4-tetrahydroacridines, benzil, different substituted aromatic aldehydes and NH4OAc, using InCl3 as the

  合成了一系列新的他克林-丝氨酸杂种，并测试了它们在纳摩尔浓度范围内以IC 50抑制乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BuChE）的能力。关键步骤是使用InCl 3作为最佳催化剂，使9-氨基烷基氨基-1,2,3,4-四氢ac啶，苄基，不同取代的芳族醛与NH 4 OAc进行一锅四组分缩合反应。发现他克林-丝氨酸杂种是胆碱酯酶的有效和选择性抑制剂。作为四组分方法向四取代咪唑的扩展，针对AChE和BuChE测试了一系列新的双-（2,4,5-三苯基-1 H-咪唑）或双（n）-卵磷脂。
• Search of antitubercular activities in tetrahydroacridines: Synthesis and biological evaluation
  作者：R.P. Tripathi、S.S. Verma、Jyoti Pandey、K.C. Agarwal、Vinita Chaturvedi、Y.K. Manju、A.K. Srivastva、A. Gaikwad、S. Sinha

  DOI：10.1016/j.bmcl.2006.07.025

  日期：2006.10

  A series of 9-substituted tetrahydroacridines were synthesized by nucleophilic substitution of chloro group with different nucleophiles in 9-chlorotetrahydroacridine (2). The latter could be obtained by POCl3 mediated cyclization of the intermediate enamine, which in turn, was prepared by acid catalyzed condensation of anthranilic acid and cyclohexanone. Most of the compounds on antitubercular evaluation against M. tuberculosis H37 Rv and H37 Ra strains exhibited potent activities with MIC 6.125-0.78 mu g/mL comparable to the standard drugs. (c) 2006 Elsevier Ltd. All rights reserved.