5-(4-trifluoromethoxyphenyl)-1H-indole | 599198-16-0

• 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-(4-trifluoromethoxyphenyl)-1H-indole
• 英文别名: 5-[4-(trifluoromethoxy)phenyl]indole；5-(4-trifluoromethoxy-phenyl)-1H-indole；5-[4-(trifluoromethoxy)phenyl]-1H-indole
• CAS: 599198-16-0
• 化学式: C₁₅H₁₀F₃NO
• 分子量: 277.246
• InChiKey: PCQVWCHZMARESC-UHFFFAOYSA-N

物化性质

• 沸点：
  383.4±42.0 °C(Predicted)
• 密度：
  1.335±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-trifluoromethoxyphenyl)-1H-indole 、 1-碘-4-(三氟甲氧基)苯 在 potassium carbonate 、 copper(I) bromide 作用下， 以 N-methyl pyrrolidinone 为溶剂， 以44%的产率得到1,5-bis-(4-trifluoromethoxy-phenyl)-1H-indole
  参考文献：
  名称：

  [EN] ARYL, ARYLOXY, AND ALKYLOXY SUBSTITUTED 1H-INDOL-3-YL GLYOXYLIC ACID DERIVATIVES AS INHIBITORS OF PLASMINOGEN ACTIVATOR INHIBITOR-1 (PAI-1)
  [FR] DERIVES D'ACIDE 1H-INDOL-3-YL GLYOXYLIQUE A SUBSTITUTION ARYLE, ARYLOXY ET ALKYLOXY EN TANT QU'INHIBITEURS DE L'INHIBITEUR DE L'ACTIVATEUR DU PLASMINOGENE-1 (PAI-1)

  摘要：

  公开号：

  WO2004052854A3
• 作为产物：
  描述：

  N-叔丁氧羰基-5-溴吲哚 在 palladium diacetate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 5-(4-trifluoromethoxyphenyl)-1H-indole
  参考文献：
  名称：

  Discovery of inhibitors of plasminogen activator inhibitor-1: Structure–activity study of 5-nitro-2-phenoxybenzoic acid derivatives

  摘要：

  Two novel series of 5-nitro-2-phenoxybenzoic acid derivatives are designed as potent PAI-1 inhibitors using hybridization and conformational restriction strategy in the tiplaxtinin and piperazine chemo types. The lead compounds 5a, 6c, and 6e exhibited potent PAI-1 inhibitory activity and favorable oral bioavailability in the rodents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.031

文献信息

• Substituted 3-alkyl and 3-arylalkyl 1H-indol-1-yl acetic acid derivatives as inhibitors of plasminogen activator inhibitor-1 (PAI-1)
  申请人：Wyeth

  公开号：US20040116488A1

  公开（公告）日：2004-06-17

  The invention formula substituted 3-alkyl and 3-arylalkyl 1H indol-1yl acetic acid derivatives which are useful as inhibitors of plasminogen activator inhibitor (PAI-1) useful for treating fibrinolytic disorders, the compounds having the structure 1 wherein: R 1 ,R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are as defined herein or a pharmaceutically acceptable salt or ester form thereof.

  这项发明提供了用作纤溶酶原激活抑制剂（PAI-1）的抑制剂的3-烷基和3-芳基烷基1H吲哚-1基乙酸衍生物，用于治疗纤溶障碍，所述化合物具有以下结构： R1、R2、R3、R4、R5、R6和R7如本文所定义或其药用可接受的盐或酯形式。
• Aryl, aryloxy, and alkyloxy substituted 1H-indol-3-yl glyoxylic acid derivatives as inhibitors of plasminogen activator inhibitor-1 (PAI-1)
  申请人：Wyeth

  公开号：US20040138283A1

  公开（公告）日：2004-07-15

  Compounds of formula I are provided: 1 wherein: R1, R2, and R3, are as defined herein, as well as pharmaceutical composition and methods using the compounds as inhibitors of plasminogen activator inhibitor (PAI-1) and as therapeutic composition for treating conditions resulting from fibrinolytic disorders, such as deep vein thrombosis, coronary heart disease and pulmonary fibrosis.

  提供了化学式I的化合物：1其中：R1、R2和R3如此定义，在此定义中，以及使用这些化合物作为纤溶酶原激活抑制剂（PAI-1）的抑制剂和作为治疗成分治疗由纤溶障碍引起的病症的药物组合物和方法，例如深静脉血栓、冠心病和肺纤维化。
• Aryl, aryloxy, and aklyloxy substituted 1H-indol-3-yl glyoxylic acid derivatives as inhibitors of plasminogen activator inhibitor-1 (PAI-1)
  申请人：Wyeth

  公开号：US07259182B2

  公开（公告）日：2007-08-21

  Compounds of formula I are provided: wherein: R1, R2, and R3, are as defined herein, as well as pharmaceutical composition and methods using the compounds as inhibitors of plasminogen activator inhibitor (PAI-1) and as therapeutic composition for treating conditions resulting from fibrinolytic disorders, such as deep vein thrombosis, coronary heart disease and pulmonary fibrosis.

  提供公式I的化合物：其中：R1，R2和R3如此定义，在药物组合物和方法中使用这些化合物作为纤溶酶原激活抑制剂（PAI-1）的抑制剂和治疗性组合物，用于治疗由纤溶异常引起的疾病，例如深静脉血栓形成，冠心病和肺纤维化。
• Aryl, aryloxy, alkyloxy substituted 1H-indol-3-yl glyoxylic acid derivatives as inhibitors of plasminogen activator inhibitor-1 (PAI-1)
  申请人：Jennings Dalton Lee

  公开号：US20070259922A1

  公开（公告）日：2007-11-08

  Compounds of formula I are provided: wherein: R1, R2, and R3, are as defined herein, as well as pharmaceutical composition and methods using the compounds as inhibitors of plasminogen activator inhibitor (PAI-1) and as therapeutic composition for treating conditions resulting from fibrinolytic disorders, such as deep vein thrombosis, coronary heart disease and pulmonary fibrosis.

  提供了I式化合物，其中：R1、R2和R3如本文所定义，以及使用该化合物作为纤溶酶原激活抑制剂（PAI-1）的抑制剂的药物组合物和方法，以及作为治疗纤溶障碍引起的疾病，例如深静脉血栓、冠心病和肺纤维化的治疗组合物。
• C(sp²)–C(sp²) Reductive Cross-Coupling of Triarylphosphines with Aryl Halides by Palladium/Nickel Co-catalysis
  作者：Zhiyong Song、Xinmiao Huang、Shuangshuang Jiang、Chen He、Ling Tang、Qian Ni、Ming Ma、Bo Chen、Yuanhong Ma

  DOI：10.1021/acs.orglett.2c02139

  日期：2022.8.5

  C(sp2)–C(sp2) reductive cross-coupling reaction of diverse triarylphosphines with a wide range of aryl halides by palladium/nickel co-catalysis. This protocol offers a unique route for the synthesis of biaryl compounds via the activation of inert C(Ar)–P bonds. The mechanistic studies demonstrate that the formation of the phosphonium salts in situ plays a key role in the catalytic cycle.

  在此，我们报告了第一个通用的 C(sp 2 )–C(sp 2 ) 还原交叉偶联反应，通过钯/镍共催化，多种三芳基膦与多种芳基卤化物发生反应。该协议为通过活化惰性 C(Ar)-P 键合成联芳基化合物提供了独特的途径。机理研究表明，鏻盐的原位形成在催化循环中起关键作用。