1-[4-(tert-Butyl)benzyl]-5-bromo-1H-indole | 481630-83-5

• 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: 1-[4-(tert-Butyl)benzyl]-5-bromo-1H-indole
• 英文别名: 5-Bromo-1-[4-(tert-butyl)benzyl]-1H-indole；5-bromo-1-(4-tert-butylbenzyl)-1H-indole；5-bromo-1-[(4-tert-butylphenyl)methyl]indole
• CAS: 481630-83-5
• 化学式: C₁₉H₂₀BrN
• 分子量: 342.279
• InChiKey: SJLWHVBPXXJWTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 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：

  1-[4-(tert-Butyl)benzyl]-5-bromo-1H-indole 、 3-甲基苯硼酸 在 3-甲基苯硼酸 作用下， 以73的产率得到1-[4-(tert-butyl)benzyl]-5-(3-methylphenyl)-1H-indole
  参考文献：
  名称：

  Substituted indole acid derivatives as inhibitors of plasminogen activator inhibitor-1 (PAI-1)

  摘要：

  该发明提供了公式1的化合物：其中：X是化学键，—CH2—或—C(O)—; R1是烷基，环烷基，—CH2-环烷基，吡啶基，—CH2-吡啶基，苯基或苄基; R2是H，烷基，环烷基，—CH2-环烷基或全氟烷基; R3是H，卤素，烷基，全氟烷基，烷氧基，环烷基，—CH2-环烷基，—NH2或—NO2; R4是可选取代的苯基，苄基，苄氧基，吡啶基或—CH2-吡啶基，或其盐或酯形式，以及使用该化合物作为纤溶酶原激活物抑制剂-1（PAI-1）的抑制剂和作为治疗纤溶异常病症的治疗组合物，例如深静脉血栓和冠心病，以及肺纤维化的方法。

  公开号：

  US20030125371A1
• 作为产物：
  描述：

  4-叔丁基苄溴 在 sodium hydride 、 氯化铵 作用下， 以 DMF (N,N-dimethyl-formamide) 、 水 为溶剂， 反应 8.5h， 以97%的产率得到1-[4-(tert-Butyl)benzyl]-5-bromo-1H-indole
  参考文献：
  名称：

  Substituted indole oxo-acetyl amino acetic acid derivatives as inhibitors of plasminogen activator inhibitor-1 (PAI-1)

  摘要：

  该发明提供了印度酮氧乙酰氨基乙酸衍生物，可用作纤溶酶原激活抑制剂-1（PAl-1）的抑制剂，用于治疗纤溶性疾病，该化合物具有以下结构：1其中：R1是烷基或可选取代的环烷基，-CH2-环烷基，吡啶基，-CH2-吡啶基，苯基或苄基; R2是氢，烷基，环烷基，-CH2-环烷基或全氟烷基; R3是氢，卤素，烷基，全氟烷基，烷氧基，环烷基，-CH2-环烷基，-NH2或-NO2; R4是可选取代的苯基，苄基，苄氧基，吡啶基或-CH2-吡啶基; R8是氢，烷基，环烷基，-CH2-环烷基，全氟烷基，芳基，取代芳基，烷基-芳基或取代烷基-芳基; R9是氢，烷基，羟基烷基，4-羟基苄基，3-吲哚亚甲基，4-咪唑亚甲基，HSCH2—，CH3SCH2CH2—，H2NC(═O)CH2—，H2NC(═O)CH2CH2—，HO2CCH2—，HO2CCH2CH2—，H2NCH2CH2CH2CH2—，H2NC(═NH)NHCH2CH2CH2—，或与R8一起取为-CH2CH2CH2—；或其药学上可接受的盐或酯形式。

  公开号：

  US20040116504A1

文献信息

• Substituted indole acid derivatives as inhibitors of plasminogen activator inhibitor-1 (PAI-1)
  申请人：Wyeth

  公开号：US20030125371A1

  公开（公告）日：2003-07-03

  This invention provides compounds of the formula: 1 wherein: X is a chemical bond, —CH 2 — or —C(O)—; R 1 is alkyl, cycloalkyl, —CH 2 -cycloalkyl, pyridinyl, —CH 2 -pyridinyl, phenyl or benzyl; R 2 is H, alkyl, cycloalkyl, —CH 2 -cycloalkyl, or perfluoroalkyl; R 3 is H, halo, alkyl, perfluoroalkyl, alkoxy, cycloalkyl, —CH 2 -cycloalkyl, —NH 2 , or —NO 2 ; R 4 is optionally substituted phenyl, benzyl, benzyloxy, pyridinyl, or —CH 2 -pyridinyl, or the salt or ester forms thereof, as well as methods for using the compounds as inhibitors of plasminogen activator inhibitor-1 (PAI-1) and as therapeutic compositions for treating conditions resulting from fibrinolytic disorders such as deep vein thrombosis and coronary heart disease, and pulmonary fibrosis.

  这项发明提供了以下结构的化合物：其中：X是化学键，-CH2-或-C(O)-；R1是烷基、环烷基、-CH2-环烷基、吡啶基、-CH2-吡啶基、苯基或苄基；R2是H、烷基、环烷基、-CH2-环烷基或全氟烷基；R3是H、卤素、烷基、全氟烷基、烷氧基、环烷基、-CH2-环烷基、-NH2或-NO2；R4是可选择地取代的苯基、苄基、苄氧基、吡啶基或-CH2-吡啶基，或其盐或酯形式，以及使用这些化合物作为纤溶酶原激活抑制剂-1（PAI-1）的抑制剂和作为治疗配方，用于治疗由纤溶障碍引起的疾病，如深静脉血栓形成、冠心病和肺纤维化。
• Substituted dihydropyrano indole-3,4-dione derivatives as inhibitors of plasminogen activator inhibitor-1 (PAI-1)
  申请人：Elokdah M. Hassan

  公开号：US20050113436A1

  公开（公告）日：2005-05-26

  Compounds of formula (I) and II) are provided wherein: X is an alkali metal or a basic amine moiety; R 1 is alkyl, cycloalkyl, —CH 2 -cycloalkyl, pyridinyl, —CH 2 -pyridinyl, phenyl or benzyl, the rings of these groups being optionally substituted; R 2 is H, halogen, alkyl, perfluoroalkyl, alkoxy, cycloalkyl, —CH 2 -cycloalkyl, —NH 2 , or —NO 2 ; R 3 is phenyl, benzyl, benzyloxy, pyridinyl, or —CH 2 -pyridinyl, with the rings of these groups being optionally substituted; or a pharmaceutically acceptable salt or ester form thereof, as well as pharmaceutical compositions and methods using these compounds as inhibitors of plasminogen activator inhibitor-1 (PAI-1) and as therapeutic compositions for treating conditions resulting from fibrinolytic disorders such as deep vein thrombosis and coronary heart disease, and pulmonary fibrosis.

  提供了化合物(I)和(II)的公式，其中：X是碱金属或碱性胺基；R1是烷基、环烷基、—CH2-环烷基、吡啶基、—CH2-吡啶基、苯基或苄基，这些基团的环可以有取代基；R2是氢、卤素、烷基、全氟烷基、烷氧基、环烷基、—CH2-环烷基、—NH2或—NO2；R3是苯基、苄基、苄氧基、吡啶基或—CH2-吡啶基，这些基团的环可以有取代基；或其药学上可接受的盐或酯形式，以及使用这些化合物作为纤溶酶原激活抑制剂-1（PAI-1）的抑制剂和治疗深静脉血栓和冠心病等纤溶障碍症状及肺纤维化的治疗组合物和方法。
• Substituted indole oxo-acetyl amino acetic acid derivatives as inhibitors of plasminogen activator inhibitor (PAI-1)
  申请人：Elokdah Mahmoud Hassan

  公开号：US20060122254A1

  公开（公告）日：2006-06-08

  This invention provides indole oxo-acetyl amino acetic acid derivatives which are useful as inhibitors of plasminogen activator inhibitor-1 (PAI-1) useful for treating fibrinolytic disorders, the compounds having the structure: wherein: R 1 is alkyl or optionally substituted cycloalkyl, —CH 2 -cycloalkyl, pyridinyl, CH 2 -pyridinyl, phenyl or benzyl; R 2 is hydrogen, alkyl, cycloalkyl, —CH 2 -cycloalkyl, or perfluoroalkyl; R 3 is hydrogen, halo, alkyl, perfluoroalkyl, alkoxy, cycloalkyl, —CH 2 -cycloalkyl, —NH 2 , or —NO 2 ; R 4 is optionally substituted phenyl, benzyl, benzyloxy, pyridinyl, or —CH 2 -pyridinyl; R 8 is hydrogen, alkyl, cycloalkyl, —CH 2 -cycloalkyl, perfluoroalkyl, aryl, substituted aryl, alkyl-aryl, or substituted alkyl-aryl; R 9 is hydrogen, alkyl, hydroxyalkyl, 4-hydroxybenzyl, 3-indolylymethylene, 4-imidazolylmethylene, HSCH 2 —, CH 3 SCH 2 CH 2 —, H 2 NC(═O)CH 2 —, H 2 NC(═O)CH 2 CH 2 —, HO 2 CCH 2 —, HO 2 CCH 2 CH 2 —, H 2 NCH 2 CH 2 CH 2 CH 2 —, H 2 NC(═NH)NHCH 2 CH 2 CH 2 —, or taken together with R 8 as —CH 2 CH 2 CH 2 —; or a pharmaceutically acceptable salt or ester form thereof.

  本发明提供了印烷氧酮乙酰氨基乙酸衍生物，其作为纤溶酶原激活抑制剂-1（PAI-1）的抑制剂而有用，用于治疗纤溶障碍，化合物具有以下结构：其中：R1是烷基或可选取代的环烷基，-CH2-环烷基，吡啶基，CH2-吡啶基，苯基或苄基；R2是氢，烷基，环烷基，-CH2-环烷基或全氟烷基；R3是氢，卤素，烷基，全氟烷基，烷氧基，环烷基，-CH2-环烷基，-NH2或-NO2；R4是可选取代的苯基，苄基，苄氧基，吡啶基或-CH2-吡啶基；R8是氢，烷基，环烷基，-CH2-环烷基，全氟烷基，芳基，取代芳基，烷基芳基或取代烷基芳基；R9是氢，烷基，羟基烷基，4-羟基苄基，3-吲哚亚甲基，4-咪唑亚甲基，HSCH2-，CH3SCH2CH2-，H2NC（═O）CH2-，H2NC（═O）CH2CH2-，HO2CCH2-，HO2CCH2CH2-，H2NCH2CH2CH2CH2-，H2NC（═NH）NHCH2CH2CH2-，或与R8一起取为-CH2CH2CH2-；或其药学上可接受的盐或酯形式。
• SUBSTITUTED INDOLE ACID DERIVATIVES AS INHIBITORS OF PLASMINOGEN ACTIVATOR INHIBITOR-1 (PAI-1)
  申请人：Elokdah Hassan Mahmoud

  公开号：US20080214647A1

  公开（公告）日：2008-09-04

  This invention provides compounds of the formula: wherein: X is a chemical bond, —CH 2 — or —C(O)—; R 1 is alkyl, cycloalkyl, —CH 2 — cycloalkyl, pyridinyl, —CH 2 -pyridinyl, phenyl or benzyl; R 2 is H, alkyl, cycloalkyl, —CH 2 -cycloalkyl, or perfluoroalkyl; R 3 is H, halo, alkyl, perfluoroalkyl, alkoxy, cycloalkyl, —CH 2 -cycloalkyl, —NH 2 , or —NO 2 ; R 4 is optionally substituted phenyl, benzyl, benzyloxy, pyridinyl, or —CH 2 -pyridinyl, or the salt or ester forms thereof, as well as methods for using the compounds as inhibitors of plasminogen activator inhibitor-1 (PAI-1) and as therapeutic compositions for treating conditions resulting from fibrinolytic disorders such as deep vein thrombosis and coronary heart disease, and pulmonary fibrosis.

  该发明提供了以下结构的化合物： 其中：X是化学键，-CH2-或-C(O)-；R1是烷基，环烷基，-CH2-环烷基，吡啶基，-CH2-吡啶基，苯基或苄基；R2是H，烷基，环烷基，-CH2-环烷基或全氟烷基；R3是H，卤素，烷基，全氟烷基，烷氧基，环烷基，-CH2-环烷基，-NH2或-NO2；R4是可选取代的苯基，苄基，苄氧基，吡啶基或-CH2-吡啶基，或其盐或酯形式，以及将这些化合物用作纤溶酶原激活抑制剂-1（PAI-1）的抑制剂和治疗深静脉血栓和冠心病等纤溶障碍引起的疾病以及肺纤维化的治疗组合物的方法。
• Substituted dihydropyrano indole-3,4-dione derivatives as inhibitiors of plasminogen activator inhibitor-1 (PAI-1)
  申请人：Wyeth

  公开号：US07101903B2

  公开（公告）日：2006-09-05

  Compounds of formula (I) and II) are provided wherein: X is an alkali metal or a basic amine moiety; R1 is alkyl, cycloalkyl, —CH2-cycloalkyl, pyridinyl, —CH2-pyridinyl, phenyl or benzyl, the rings of these groups being optionally substituted; R2 is H, halogen, alkyl, perfluoroalkyl, alkoxy, cycloalkyl, —CH2-cycloalkyl, —NH2, or —NO2; R3 is phenyl, benzyl, benzyloxy, pyridinyl, or —CH2-pyridinyl, with the rings of these groups being optionally substituted; or a pharmaceutically acceptable salt or ester form thereof, as well as pharmaceutical compositions and methods using these compounds as inhibitors of plasminogen activator inhibitor-1 (PAI-1) and as therapeutic compositions for treating conditions resulting from fibrinolytic disorders such as deep vein thrombosis and coronary heart disease, and pulmonary fibrosis.

  提供了式(I)和(II)的化合物，其中：X是碱金属或碱性胺基基团；R1是烷基、环烷基、—CH2-环烷基、吡啶基、—CH2-吡啶基、苯基或苄基，这些基团的环可以选择性地被取代；R2是H、卤素、烷基、全氟烷基、烷氧基、环烷基、—CH2-环烷基、—NH2或—NO2；R3是苯基、苄基、苄氧基、吡啶基或—CH2-吡啶基，这些基团的环可以选择性地被取代；或其药学上可接受的盐或酯形式，以及使用这些化合物作为纤溶酶原激活抑制剂-1（PAI-1）的抑制剂和治疗深静脉血栓和冠心病等纤溶障碍症状以及肺纤维化的治疗组合物和方法。