5-氯-1-苄基吲哚-2-羧酸 | 1026645-16-8

• 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
• 中文名称: 5-氯-1-苄基吲哚-2-羧酸
• 英文名称: 5-chloro-1-benzylindole-2-carboxylic acid
• 英文别名: 1-benzyl-5-chloro-1H-indole-2-carboxylic acid；1-benzyl-5-chloroindole-2-carboxylic acid
• CAS: 1026645-16-8
• 化学式: C₁₆H₁₂ClNO₂
• 分子量: 285.73
• InChiKey: ZKLFRWIEGLBBEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-氯-1-苄基吲哚-2-羧酸 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  The discovery of novel indole-2-carboxamides as cannabinoid CB1 receptor antagonists

  摘要：

  The discovery and structure-activity relationship of a novel series of indole-2-carboxamide antagonists of the cannabinoid CB1 receptor is disclosed. Compound 26i was found to be a high potency, selective cannabinoid CB1 antagonist. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.104
• 作为产物：
  描述：

  ethyl 1-benzyl-5-chloroindole-2-carboxylate 在 水 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 5-氯-1-苄基吲哚-2-羧酸
  参考文献：
  名称：

  The discovery of novel indole-2-carboxamides as cannabinoid CB1 receptor antagonists

  摘要：

  The discovery and structure-activity relationship of a novel series of indole-2-carboxamide antagonists of the cannabinoid CB1 receptor is disclosed. Compound 26i was found to be a high potency, selective cannabinoid CB1 antagonist. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.104

文献信息

• Synthesis of Cyclobutane-Fused Tetracyclic Scaffolds via Visible-Light Photocatalysis for Building Molecular Complexity
  作者：Martins S. Oderinde、Edna Mao、Antonio Ramirez、Joseph Pawluczyk、Christine Jorge、Lyndon A. M. Cornelius、James Kempson、Muthalagu Vetrichelvan、Manivel Pitchai、Anuradha Gupta、Arun Kumar Gupta、Nicholas A. Meanwell、Arvind Mathur、T. G. Murali Dhar

  DOI：10.1021/jacs.9b12129

  日期：2020.2.12

  describe the synthesis through visible-light photocatalysis of novel functionalized tetracyclic scaffolds that incorporate a fused azabicyclo[3.2.0]heptan-2-one motif, which are structurally interesting cores with potential in natural product synthesis and drug discovery. The synthetic approach involves an intramolecular [2+2] cycloaddition with concomitant dearomatization of the heterocycle via an energy

  我们描述了通过可见光光催化合成新型功能化四环支架，这些支架结合了一个融合的氮杂双环 [3.2.0] 庚烷-2-one 基序，这些基序是结构有趣的核心，在天然产物合成和药物发现中具有潜力。合成方法涉及分子内 [2+2] 环加成反应，同时通过铱基光敏剂促进的能量转移过程使杂环脱芳构化，以从相对简单的非手性前体构建具有三个立体中心的复杂分子结构。这些基于稠合氮杂双环[3.2.0]庚烷-2-one的四环以高产率（通常> 99％）和优异的非对映选择性（> 99：1）获得。具有烷基的溴取代的四环二氢吲哚衍生物的后期衍生化，采用温和的 Negishi CC 键形成方案作为增加结构多样性的一种手段，提供了额外的模块化，能够为药物化学提供有价值的构建模块。DFT 计算用于计算烯烃系链前驱体的 T1-S0 自由能隙，并基于三重态能量转移和过渡态能量可行性预测其反应性。
• Indole amide derivatives: synthesis, structure–activity relationships and molecular modelling studies of a new series of histamine H1-receptor antagonists
  作者：Sandra Battaglia、Enrico Boldrini、Federico Da Settimo、Giulio Dondio、Concettina La Motta、Anna Maria Marini、Giampaolo Primofiore

  DOI：10.1016/s0223-5234(99)80044-0

  日期：1999.2

  A number of indole amide derivatives bearing a basic side chain, in which the indole ring replaces the isoster benzimidazole nucleus typical of some well-known antihistamines, were prepared and tested for their H-1-antihistaminic activity. The 1-benzyl-3-indolecarboxamides 32-42 showed antihistaminic (H-1) activity (pA(2) 6-8); the 3-indolylglyoxylylamides 7-16 and the 2-indolecarboxamides 48-56 showed little or no activity. Insertion of the basic side chain of the active 3-indolecarboxamide derivatives into a piperazine ring (compounds 57-59) led to a dramatic loss of activity. All the active compounds proved to be competitive antagonists, since the values of the regression slope were not statistically different from 1. The most active compounds, 32, 33, 38-41, were also tested both in vitro for their anticholinergic activity and in vivo for their ability to antagonize histamine-induced cutaneous vascular permeability in rats. The biological results and the structure-activity relationships of the novel compounds are discussed in the light of molecular modelling studies, taking the molecule of astemizole as a model, and referring to proposed H-1-receptor pharmacophore models. (C) Elsevier, Paris.
• The discovery of novel indole-2-carboxamides as cannabinoid CB1 receptor antagonists
  作者：Phillip M. Cowley、James Baker、David R. Barn、Kirsteen I. Buchanan、Ian Carlyle、John K. Clark、Thomas R. Clarkson、Maureen Deehan、Darren Edwards、Richard R. Goodwin、David Jaap、Yasuko Kiyoi、Chris Mort、Ronald Palin、Alan Prosser、Glenn Walker、Nick Ward、Grant Wishart、Trevor Young

  DOI：10.1016/j.bmcl.2010.10.104

  日期：2011.1

  The discovery and structure-activity relationship of a novel series of indole-2-carboxamide antagonists of the cannabinoid CB1 receptor is disclosed. Compound 26i was found to be a high potency, selective cannabinoid CB1 antagonist. (C) 2010 Elsevier Ltd. All rights reserved.