5-butyl-2-(4-methoxyphenyl)-1H-indole | 906770-73-8

• 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: 5-butyl-2-(4-methoxyphenyl)-1H-indole
• 英文别名: 5-n-butyl-2-(4-methoxyphenyl)indole
• CAS: 906770-73-8
• 化学式: C₁₉H₂₁NO
• 分子量: 279.382
• InChiKey: KBSQQBDGNXHQNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  25.02
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  5-butyl-2-(4-methoxyphenyl)-1H-indole 、 3,4-dibromo-1-(tert-butyldimethylsilyl)-1H-pyrrole-2,5-dione 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 3-bromo-4-(5-butyl-2-(4-methoxyphenyl)-1H-indol-3-yl)-1-(tert-butyldimethylsilyl)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Antibacterial activity of a novel series of 3-bromo-4-(1H-3-indolyl)-2,5-dihydro-1H-2,5-pyrroledione derivatives – An extended structure–activity relationship study

  摘要：

  Compounds containing 3-bromo-2,5-dihydro-1H-2,5-pyrroledione and indole substructures were found to have antibacterial activity against resistant strains of Staphylococcus aureus and some other Gram positive bacteria. The investigated compounds exhibit minimal inhibition concentrations (MICs) lower than those of common antibiotics like vancomycin or ciprofloxacin. Activity against multiresistant strains suggests a mechanism of action different from common antibiotics. This might be important in circumventing existing resistance mechanisms. Here we report about the antibacterial activity in an extended structure-activity relationship study. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.05.009
• 作为产物：
  描述：

  4-正丁基苯胺 、 alpha-溴-4-甲氧基苯乙酮 在 N,N-二甲基苯胺 作用下， 以 xylene 为溶剂， 反应 15.0h， 以53%的产率得到5-butyl-2-(4-methoxyphenyl)-1H-indole
  参考文献：
  名称：

  Antibacterial activity of a novel series of 3-bromo-4-(1H-3-indolyl)-2,5-dihydro-1H-2,5-pyrroledione derivatives – An extended structure–activity relationship study

  摘要：

  Compounds containing 3-bromo-2,5-dihydro-1H-2,5-pyrroledione and indole substructures were found to have antibacterial activity against resistant strains of Staphylococcus aureus and some other Gram positive bacteria. The investigated compounds exhibit minimal inhibition concentrations (MICs) lower than those of common antibiotics like vancomycin or ciprofloxacin. Activity against multiresistant strains suggests a mechanism of action different from common antibiotics. This might be important in circumventing existing resistance mechanisms. Here we report about the antibacterial activity in an extended structure-activity relationship study. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.05.009

文献信息

• Aniline‐Promoted Cyclization–Replacement Cascade Reactions of 2‐Hydroxycinnamaldehydes with Various Carbonic Nucleophiles through In Situ Formed <i>N</i> , <i>O</i> ‐Acetals
  作者：Chenguang Yu、He Huang、Xiangmin Li、Yueteng Zhang、Hao Li、Wei Wang

  DOI：10.1002/chem.201601112

  日期：2016.6.27

  of N,O‐acetals in an aminocatalytic fashion for organic synthesis. Unlike widely used strategies requiring the use of acids and/or elevated temperatures, direct replacement of the amine component of the N,O‐acetals by carbon‐centered nucleophiles for C−C bond formation is realized under mild reaction conditions. Furthermore, without necessary preformation of the N,O‐acetals, an amine‐catalyzed in situ

  在这项研究中，我们报告了以氨基催化方式利用N，O-乙缩醛的新反应性进行有机合成。与广泛使用的需要使用酸和/或升高温度的策略不同，在温和的反应条件下，可以用碳中心的亲核试剂直接取代N，O-缩醛的胺成分以形成C-C键。此外，在不需要预先形成N，O-缩醛的情况下，胺催化的N，O原位形成缩醛被开发出来。将两个反应耦合到一个反应釜中即可实现催化过程。我们证明了使用简单的苯胺作为反式-2-羟基肉桂醛与各种碳亲核试剂（包括吲哚，吡咯，萘，酚和甲硅烷基烯醇醚）的环化-取代级联反应的促进剂。该方法为结构上多样化的“特权” 2取代2 H色酮提供了另一种方法。新工艺的合成能力还通过在天然产物降钙素E的2步合成中的应用以及将2取代的2 H-色烯部分轻松安装到具有生物活性的吲哚中而得到了证明。
• Antimitotic activities of 2-phenylindole-3-carbaldehydes in human breast cancer cells
  作者：Doris Kaufmann、Michaela Pojarová、Susanne Vogel、Renate Liebl、Robert Gastpar、Dietmar Gross、Tsuyuki Nishino、Tobias Pfaller、Erwin von Angerer

  DOI：10.1016/j.bmc.2007.05.030

  日期：2007.8

  Small molecules such as indoles are attractive as inhibitors of tubulin polymerization. Thus a number of 2-phenylindole-3-carbaldehydes with lipophilic substituents in both aromatic rings was synthesized and evaluated for antitumor activity in MDA-MB 231 and MCF-7 breast cancer cells. Some 5-alkylindole derivatives with a 4-methoxy group in the 2-phenyl ring strongly inhibit the growth of breast cancer cells with IC50 values of 5-20 nM. Their action can be rationalized by the cell cycle arrest in G(2)/M phase due to the inhibition of tubulin polymerization. (c) 2007 Elsevier Ltd. All rights reserved.