2-hexyl-1-methyl-1H-indole | 95104-11-3

• 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-hexyl-1-methyl-1H-indole
• 英文别名: 2-hexyl-1-methylindole
• CAS: 95104-11-3
• 化学式: C₁₅H₂₁N
• 分子量: 215.338
• InChiKey: KUSKRIQSDDONEN-UHFFFAOYSA-N

物化性质

• 沸点：
  337.3±11.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3-甲基戊二酸酐 、 2-hexyl-1-methyl-1H-indole 在 二甲基氯化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 3.5h， 以95%的产率得到5-(2-hexyl-1-methyl-1H-indol-3-yl)-3-methyl-5-oxo-pentanoic acid
  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
• 作为产物：
  描述：

  1H-吲哚-2-甲醛 在 palladium 10% on activated carbon 、 氢气 、 potassium hydroxide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 二甲基亚砜 为溶剂， 反应 13.0h， 生成 2-hexyl-1-methyl-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

• Selective Catalytic C–H Alkylation of Alkenes with Alcohols
  作者：Dong-Hwan Lee、Ki-Hyeok Kwon、Chae S. Yi

  DOI：10.1126/science.1208839

  日期：2011.9.16

  A ruthenium catalyst forms carbon-carbon bonds between olefins and alcohols while liberating only water as a by-product. Alkenes and alcohols are among the most abundant and commonly used organic feedstock in industrial processes. We report a selective catalytic alkylation reaction of alkenes with alcohols that forms a carbon-carbon bond between vinyl carbon-hydrogen (C–H) and carbon-hydroxy centers

  钌催化剂在烯烃和醇之间形成碳-碳键，同时仅释放水作为副产物。烯烃和醇是工业过程中最丰富和最常用的有机原料。我们报告了烯烃与醇的选择性催化烷基化反应，该反应在乙烯基碳氢（C-H）和碳-羟基中心之间形成碳-碳键，同时失去水。阳离子钌络合物 [(C6H6)(PCy3)(CO)RuH]+BF4–（Cy，环己基）可在 75°C 至 110°C 的温度范围内在 2 至 8 小时内催化溶液中的烷基化，并耐受广泛的底物官能团，包括胺和羰基。初步的机理研究与醇的 Friedel-Crafts 型亲电活化不一致，
• [EN] 5-OXO-ETE RECEPTOR ANTAGONIST COMPOUNDS<br/>[FR] COMPOSÉS ANTAGONISTES DES RÉCEPTEURS 5-OXO-ETE
  申请人：UNIV MCGILL

  公开号：WO2010127452A1

  公开（公告）日：2010-11-11

  The present invention relates to novel pharmaceutically-useful compounds which are antagonists of the 5-oxo-ETE receptors, such as the OXE receptor. These compounds have use as therapeutic and/or prophylactic agents for diseases characterized by tissue eosinophilia, such as inflammatory conditions including respiratory diseases. The invention also relates to pharmaceutical compositions, to the use of such compounds and compositions as medicaments, and to therapeutic methods.

  本发明涉及一种新型的药用化合物，它们是5-oxo-ETE受体的拮抗剂，如OXE受体。这些化合物可用作治疗和/或预防组织嗜麻细胞增多等疾病的药物，如包括呼吸道疾病在内的炎症性疾病。该发明还涉及制药组合物，以及将这些化合物和组合物用作药物、以及治疗方法。
• Gold-Catalyzed Tandem Cycloisomerization/Functionalization of in Situ Generated α-Oxo Gold Carbenes in Water
  作者：Cang-Hai Shen、Long Li、Wei Zhang、Shuang Liu、Chao Shu、Yun-Er Xie、Yong-Fei Yu、Long-Wu Ye

  DOI：10.1021/jo501872h

  日期：2014.10.3

  A gold-catalyzed tandem cycloisomerization/functionalization of in situ generated α-oxo gold carbenes in water has been developed, which provides ready access to highly functionalized indole derivatives from o-alkynyl anilines and ynamides. Importantly, gold serves dual catalytic roles to mediate both the cycloisomerization of o-alkynyl anilines and the intermolecular oxidation of ynamides at the same

  已经开发了一种金催化的在水中原位生成的α-氧代金卡宾的串联环异构化/功能化方法，该方法可以方便地从邻炔基苯胺和乙酰胺中获得高度官能化的吲哚衍生物。重要的是，金具有双重催化作用，可同时介导邻炔基苯胺的环异构化和乙酰胺的分子间氧化，从而提供了一种新型的同时串联催化。该方法的其他显着特征是使用容易获得的起始原料，简单的步骤以及温和的反应条件。
• 5-OXO-ETE RECEPTOR ANTAGONIST COMPOUNDS
  申请人：Powell William S.

  公开号：US20120122942A1

  公开（公告）日：2012-05-17

  The present invention relates to novel pharmaceutically-useful compounds which are antagonists of the 5-oxo-ETE receptors, such as the OXE receptor. These compounds have use as therapeutic and/or prophylactic agents for diseases characterized by tissue eosinophilia, such as inflammatory conditions including respiratory diseases. The invention also relates to pharmaceutical compositions, to the use of such compounds and compositions as medicaments, and to therapeutic methods.

  本发明涉及一种新型药用化合物，其为5-oxo-ETE受体（如OXE受体）的拮抗剂。这些化合物可用作治疗和/或预防组织嗜酸性细胞增多症的疾病的治疗剂和/或预防剂，例如包括呼吸系统疾病在内的炎症性疾病。本发明还涉及制药组合物，使用这种化合物和组合物作为药物以及治疗方法。
• 5-oxo-ETE receptor antagonist compounds
  申请人：Powell William S.

  公开号：US08809382B2

  公开（公告）日：2014-08-19

  The present invention relates to novel pharmaceutically-useful compounds which are antagonists of the 5-oxo-ETE receptors, such as the OXE receptor. These compounds have use as therapeutic and/or prophylactic agents for diseases characterized by tissue eosinophilia, such as inflammatory conditions including respiratory diseases. The invention also relates to pharmaceutical compositions, to the use of such compounds and compositions as medicaments, and to therapeutic methods.

  本发明涉及一种新的药用化合物，它们是5-oxo-ETE受体的拮抗剂，例如OXE受体。这些化合物可用作治疗和/或预防组织嗜酸性粒细胞增多的疾病的药物，例如包括呼吸系统疾病在内的炎症性疾病。本发明还涉及制药组合物、使用这些化合物和组合物作为药物以及治疗方法。