5-[(3,3-dimethylbutanoyl)-amino]-1-(2-fluorobenzyl)-1H-indole-2-carboxylic acid | 509150-40-7

• 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-[(3,3-dimethylbutanoyl)-amino]-1-(2-fluorobenzyl)-1H-indole-2-carboxylic acid
• 英文别名: 5-[(3,3-Dimethylbutanoyl)amino]-1-(2-fluorobenzyl)-1H-indole-2-carboxylic acid；5-(3,3-dimethylbutanoylamino)-1-[(2-fluorophenyl)methyl]indole-2-carboxylic acid
• CAS: 509150-40-7
• 化学式: C₂₂H₂₃FN₂O₃
• 分子量: 382.435
• InChiKey: VGZNYMWXGVXZPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  71.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-[(3,3-dimethylbutanoyl)-amino]-1-(2-fluorobenzyl)-1H-indole-2-carboxylic acid 在 劳森试剂 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-(3,3-dimethylbutanethioylamino)-1-[(2-fluorophenyl)methyl]-N-phenylindole-2-carboxamide
  参考文献：
  名称：

  Novel, selective indole-based ECE inhibitors: Lead optimization via solid-phase and classical synthesis

  摘要：

  A novel class of indole-based endothelia-converting enzyme (ECE) inhibitors was identified by high throughput screening. We report systematic optimization of this compound class by means of classical and solid-phase chemistry. Optimized compounds with a bisarylamide side chain at the 2-position of the indole skeleton exhibit low-nanomolar activity on ECE. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.085
• 作为产物：
  描述：

  ethyl 1-(2-fluorobenzyl)-5-nitro-1H-indole-2-carboxylate 在 palladium on activated charcoal lithium hydroxide 、 ammonium formate 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 5-[(3,3-dimethylbutanoyl)-amino]-1-(2-fluorobenzyl)-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  Novel, selective indole-based ECE inhibitors: Lead optimization via solid-phase and classical synthesis

  摘要：

  A novel class of indole-based endothelia-converting enzyme (ECE) inhibitors was identified by high throughput screening. We report systematic optimization of this compound class by means of classical and solid-phase chemistry. Optimized compounds with a bisarylamide side chain at the 2-position of the indole skeleton exhibit low-nanomolar activity on ECE. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.085

文献信息

• Use of substituted 2,5-diamidoindoles for the treatment of urological diseases
  申请人：Erguden Jens

  公开号：US20060183753A1

  公开（公告）日：2006-08-17

  The present invention relates to the use of 2,5-diamidoindole derivatives for the preparation of medicaments for treating urological disorders in humans and/or animals.RCK 41-Foreign Countries

  本发明涉及使用2,5-二氨基吲哚衍生物制备用于治疗人类和/或动物泌尿系统疾病的药物。RCK 41-外国国家。
• Substituted 2 5-diamidoindoles as ece inhibitors for the treatment of cardiovascular diseases
  申请人：Erguden Jens-Kerim

  公开号：US20050038101A1

  公开（公告）日：2005-02-17

  The invention relates to compounds of formula (I), to a method for the production thereof, and to the use of the same as pharmaceuticals for the treatment of diseases in humans and/or animals.

  本发明涉及公式（I）的化合物，其制备方法和将其用作治疗人类和/或动物疾病的药物。
• Substituted 2,5-diamidoindoles as ECE inhibitors for the treatment of cardiovascular diseases
  申请人：Bayer HealthCare AG

  公开号：US07045544B2

  公开（公告）日：2006-05-16

  The invention relates to compounds of formula (I), to a method for the production thereof, and to the use of the same as pharmaceuticals for the treatment of diseases in humans and/or animals

  本发明涉及公式（I）的化合物，其制备方法以及将其用作人类和/或动物疾病治疗药物的用途。
• [EN] USE OF SUBSTITUTED 2,5-DIAMIDOINDOLES FOR THE TREATMENT OF UROLOGICAL DISEASES<br/>[FR] UTILISATION DE 2,5-DIAMIDOINDOLES SUBSTITUES POUR LE TRAITEMENT DE MALADIES UROLOGIQUES
  申请人：BAYER HEALTHCARE AG

  公开号：WO2004056768A3

  公开（公告）日：2004-08-05
• SUBSTITUIERTE 2,5-DIAMIDOINDOLE ALS ECE-INHIBITOREN ZUR BEHANDLUNG VON KARDIOVASKULÄREN ERKRANKUNGEN
  申请人：Bayer HealthCare AG

  公开号：EP1432415A1

  公开（公告）日：2004-06-30