2-heptyl-1H-indole | 54687-20-6

• 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: 2-heptyl-1H-indole
• 英文别名: 2-heptyl-indole
• CAS: 54687-20-6
• 化学式: C₁₅H₂₁N
• 分子量: 215.338
• InChiKey: XZMDPQNUMUUULV-UHFFFAOYSA-N

物化性质

• 熔点：
  61 °C
• 沸点：
  353.8±11.0 °C(Predicted)
• 密度：
  0.991±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-heptyl-1H-indole 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 Lithium; 2-heptyl-indole-1-carboxylate
  参考文献：
  名称：

  Carbon dioxide: a reagent for simultaneous protection of nucleophilic centers and the activation of alternative locations to electrophilic attack. V. Activation of the 2-alkyl group of a 2-alkylindole toward proton loss and subsequent electrophilic substitution

  摘要：

  DOI：

  10.1021/ja00281a061
• 作为产物：
  描述：

  1H-吲哚-2-甲醛 在 palladium 10% on activated carbon 、 氢气 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 9.5h， 生成 2-heptyl-1H-indole
  参考文献：
  名称：

  Inhibition of 5-Oxo-6,8,11,14-eicosatetraenoic Acid-Induced Activation of Neutrophils and Eosinophils by Novel Indole OXE Receptor Antagonists

  摘要：

  5-Oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) is a 5-lipoxygenase product that is a potent granulocyte chemoattractant, which induces the infiltration of eosinophils into human skin when injected intradermally. It could therefore be an important proinflammatory mediator in eosinophilic diseases such as asthma and allergic rhinitis, and the OXE receptor, which mediates its actions, is therefore an attractive drug target. Using a Structure-based approach in which substituents mimicking the essential polar (C-1-C-5) and hydrophobic (C-15-C-20) regions of 5-oxo-ETE were incorporated on an indole scaffold, we identified two potent selective OXE antagonists with IC50 values of about 30 nM Neither compound displayed agonist activity and both inhibited 5-oxo-ETE-induced chemotaxis and actin polymerization and were relatively resistant to metabolism by rat liver homogenates. The active enantiomers of these racemic antagonists were even more potent, with IC50 values of <10 nM. These selective OXE antagonists could potentially be useful therapeutic agents in allergic diseases such as asthma.

  DOI：

  10.1021/jm401292m

文献信息

• Acylated indole derivatives, processes for their preparation and pharmaceutical compositions and drugs comprising them
  申请人：TEIJIN LIMITED

  公开号：EP0022634A1

  公开（公告）日：1981-01-21

  The invention provides acylated indole derivatives of the following formula wherein R' represents a hydrogen atom or a lower alkyl group, R2 represents a lower alkyl group, R3 represents a hydrogen atom or a lower alkyl group, R4 represents a hydrogen atom, a hydroxyl group, a halogen atom, a lower alkyl group. or a lower alkoxy group, Z represents a phenyl or thienyl group or a phenyl or thienyl group substituted by the group R4, Y represents a bond, -0-, -S-, -SO-, or -SO2-, A represents a hydrogen atom, a lower alkyl group, a lower acyl group, a phenyl group, a phenylalkyl group, a 5- or 6-membered heterocyclic group having an oxygen, sulfur or nitrogen atom, or a phenyl, alkylphenyl or 5- or 6-membered O-, S- or N-containing heterocyclic group substituted by the group R4, and n represents zero or an integer of 1 to 10 provided that when n is zero, Y represents a bond and A represents a lower acyl group; or optically active isomers or salts thereof. The invention also provides processes for producing the acylated indole derivatives by acylating a 3-unsubstituted indole derivative or 3-unsubstituted tetrahydroindole derivative with an acid anhydride in the presence of hydrogen iodide. Some of acylated indole derivatives have biological activities, particularly the ability to inhibit platelet aggregation with a reduced tendency to ulcer formation.

  本发明提供下式的酰化吲哚衍生物 其中 R' 代表氢原子或低级烷基；R2 代表低级烷基；R3 代表氢原子或低级烷基；R4 代表氢原子、羟基、卤素原子、低级烷基或低级烷氧基，Z 代表苯基或噻吩基，或被基团 R4 取代的苯基或噻吩基，Y 代表键、-0-、-S-、-SO- 或-SO2-，A 代表氢原子、低级烷基、低级酰基、苯基、苯基烷基、具有氧、硫或氮原子的 5 或 6 元杂环基团，或被基团 R4 取代的苯基、烷基苯基或含 O、S 或 N 的 5 或 6 元杂环基团，且 n 代表零或 1 至 10 的整数，但当 n 为零时，Y 代表键，A 代表低级酰基；或其光学活性异构体或盐。 本发明还提供了通过在碘化氢存在下用酸酐酰化 3-未取代的吲哚衍生物或 3-未取代的四氢吲哚衍生物来生产酰化吲哚衍生物的工艺。 一些酰化吲哚衍生物具有生物活性，特别是能够抑制血小板聚集，减少溃疡形成的倾向。
• 5-Oxo-ETE Receptor Antagonists
  作者：Vivek Gore、Pranav Patel、Chih-Tsung Chang、Sashikala Sivendran、Namin Kang、Yannick P. Ouedraogo、Sylvie Gravel、William S. Powell、Joshua Rokach

  DOI：10.1021/jm400480j

  日期：2013.5.9

  5-Oxo-ETE is the most powerful eosinophil chemoattractant among lipid mediators. Eosinophil infiltration into the lungs of asthmatics may be responsible for the late phase of inflammatory asthma. We have designed and synthesized a 5-oxo-ETE receptor antagonist, the purpose of which is to prevent eosinophil migration to the lung during an asthma attack and thereby reduce asthma symptoms.
• 3-Bromo-4-(1H-3-indolyl)-2,5-dihydro-1H-2,5-pyrroledione derivatives as new lead compounds for antibacterially active substances
  作者：Siavosh Mahboobi、Emerich Eichhorn、Alfred Popp、Andreas Sellmer、Sigurd Elz、Ute Möllmann

  DOI：10.1016/j.ejmech.2005.10.006

  日期：2006.2

  A number of new 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, Mycobacterium smegmatis and some other Gram positive bacteria. The investigated compounds exhibit minimal inhibition concentrations (MIC's) lower than those of ciprofloxacin, vancomycin and doxycycline resp. A different spectrum of activity, suggests a mechanism of action different to vancomycin and doxycycline. This might be important in circumventing existing resistance mechanisms. Here we report about the synthesis and on the antibacterial activity in a structure activity relationship study. (c) 2005 Elsevier SAS. All rights reserved.
• KATRITZKY A. R.; AKUTAGAWA KUNIHIKO, J. AMER. CHEM. SOC., 108,(1986) N 21, 6808-6809
  作者：KATRITZKY A. R.、 AKUTAGAWA KUNIHIKO

  DOI：——

  日期：——
• Inhibition of 5-Oxo-6,8,11,14-eicosatetraenoic Acid-Induced Activation of Neutrophils and Eosinophils by Novel Indole OXE Receptor Antagonists
  作者：Vivek Gore、Sylvie Gravel、Chantal Cossette、Pranav Patel、Shishir Chourey、Qiuji Ye、Joshua Rokach、William S. Powell

  DOI：10.1021/jm401292m

  日期：2014.1.23

  5-Oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) is a 5-lipoxygenase product that is a potent granulocyte chemoattractant, which induces the infiltration of eosinophils into human skin when injected intradermally. It could therefore be an important proinflammatory mediator in eosinophilic diseases such as asthma and allergic rhinitis, and the OXE receptor, which mediates its actions, is therefore an attractive drug target. Using a Structure-based approach in which substituents mimicking the essential polar (C-1-C-5) and hydrophobic (C-15-C-20) regions of 5-oxo-ETE were incorporated on an indole scaffold, we identified two potent selective OXE antagonists with IC50 values of about 30 nM Neither compound displayed agonist activity and both inhibited 5-oxo-ETE-induced chemotaxis and actin polymerization and were relatively resistant to metabolism by rat liver homogenates. The active enantiomers of these racemic antagonists were even more potent, with IC50 values of <10 nM. These selective OXE antagonists could potentially be useful therapeutic agents in allergic diseases such as asthma.