9-phenylethylpyrido[3,4-b]indole | 94258-13-6

• 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-phenylethylpyrido[3,4-b]indole
• 英文别名: 9-phenethyl-9H-pyrido[3,4-b]indole；9-phenylethyl-9H-pyrido[3,4-b]indole；9-<2-Phenyl-aethyl>-norharman；9-phenethyl-9H-β-carboline；9-(2-Phenylethyl)pyrido[3,4-b]indole
• CAS: 94258-13-6
• 化学式: C₁₉H₁₆N₂
• 分子量: 272.349
• InChiKey: MCPRSRMRWSYGJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  17.82
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  9-phenylethylpyrido[3,4-b]indole 在 sodium tetrahydroborate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 76.0h， 生成 2-methyl-9-phenylethyl-1,2,3,4-tetrahydropyrido[3,4-b]indole
  参考文献：
  名称：

  Beta and gamma carboline derivatives as potential anti-Alzheimer agents: A comparison

  摘要：

  Nine novel beta- and gamma-carboline derivatives bearing either methyl-, propargyl- or phenethyl-residues at the indole nitrogen were synthesized and tested as potential anti-Alzheimer drugs. Antagonism of recombinantly expressed NMDA receptors, inhibition of cholinesterases, and radical scavenging properties were determined for all compounds. Some were additionally tested in vivo for their ability to reverse scopolamine-induced cognitive impairment in an 8-arm radial maze experiment with rats. For the most promising candidates, the interaction with muscarinic M-1 receptors was also investigated. With this set of compounds assays the influence of the scaffold itself and the substituents can be investigated separately. 5-Methyl-gamma-carboline (6) was the most potent (0.25 mu mol/100 g b.w.) compound in the in vivo test and might be a good starting point for the development of novel anti-Alzheimer drugs. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.048
• 作为产物：
  描述：

  3,4-二溴吡啶 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 tris-(dibenzylideneacetone)dipalladium(0) 、 四(三苯基膦)钯 、 potassium carbonate 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 32.0h， 生成 9-phenylethylpyrido[3,4-b]indole
  参考文献：
  名称：

  通过顺序的位点选择性Pd催化的C–C，C–N偶联反应，可以有效地从常见的起始原料中获得β-和γ-咔啉

  摘要：

  据报道，有两种有效且实用的方法可从3,4-二溴吡啶作为一种常见的起始原料合成β-和γ-咔啉衍生物。的β -carbolines通过位点选择性Pd催化的C-C耦合与制备ö -bromophenylboronic酸和随后的环化通过双C-N与胺偶联。γ-咔啉是由相同的原料通过C–N与苯胺偶联，然后由多米诺C–C / C–N与邻溴苯硼酸偶联而制得的。

  DOI：

  10.1016/j.tet.2019.130569

文献信息

• Copper-Catalyzed Synthesis of β- and δ-Carbolines by Double N-Arylation of Primary Amines
  作者：Tran Quang Hung、Tuan Thanh Dang、Peter Langer、Ban Van Phuc、Ha Nam Do、Nguyen Minh Quan、Nguyen Ngoc Tuan、Nguyen Quang An、Nguyen Van Tuyen、Hoang Le Tuan Anh

  DOI：10.1055/s-0040-1720461

  日期：2021.6

  Two efficient and practical approaches are reported for the synthesis of β- and δ-carbolines from 3,4-dibromopyridine. The synthesis is based on site-selective Cu-catalyzed double C–N coupling reactions and subsequent annulations by twofold Pd-catalyzed C–N coupling with amines.

  据报道，有两种有效且实用的方法可从3,4-二溴吡啶合成β-和δ-咔啉。合成基于位点选择性Cu催化的双C–N偶联反应，以及随后通过胺与Pd催化的C–N的两倍偶联而进行的环化反应。