1-(7-aza-bicyclo[2.2.1]heptan-7-yl)-2-(4-(2-(4-(3-(4-acetylpiperazin-1-yl)-2-hydroxypropyl)piperazin-1-yl)ethyl)-5-(3,5-dimethylphenyl)-6H-thieno[2,3-b]pyrrol-2-yl)-2-methylpropan-1-one | 666850-72-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(7-aza-bicyclo[2.2.1]heptan-7-yl)-2-(4-(2-(4-(3-(4-acetylpiperazin-1-yl)-2-hydroxypropyl)piperazin-1-yl)ethyl)-5-(3,5-dimethylphenyl)-6H-thieno[2,3-b]pyrrol-2-yl)-2-methylpropan-1-one
• 英文别名: 2-[4-[2-[4-[3-(4-acetylpiperazin-1-yl)-2-hydroxypropyl]piperazin-1-yl]ethyl]-5-(3,5-dimethylphenyl)-6H-thieno[2,3-b]pyrrol-2-yl]-1-(7-azabicyclo[2.2.1]heptan-7-yl)-2-methylpropan-1-one
• CAS: 666850-72-2
• 化学式: C₃₉H₅₆N₆O₃S
• 分子量: 688.978
• InChiKey: WDDRUCUWAOFJED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  49
• 可旋转键数：
  10
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-4-(2-chloroethyl)-5-(3,5-dimethylphenyl)-6H-thieno[2,3-b]pyrrole 、 1-[4-(2-Hydroxy-3-piperazin-1-ylpropyl)piperazin-1-yl]ethanone 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 1-(7-aza-bicyclo[2.2.1]heptan-7-yl)-2-(4-(2-(4-(3-(4-acetylpiperazin-1-yl)-2-hydroxypropyl)piperazin-1-yl)ethyl)-5-(3,5-dimethylphenyl)-6H-thieno[2,3-b]pyrrol-2-yl)-2-methylpropan-1-one
  参考文献：
  名称：

  Synthesis and structure–activity relationships of thieno[2,3-b]pyrroles as antagonists of the GnRH receptor

  摘要：

  A new class of small-molecule GnRH antagonists, the thieno[2,3-b]pyrroles, was designed. Herein, the synthesis and structure-activity relationships are described. Substitution at the C4 position was investigated; during this study, it was observed that introducing piperazines and piperidines improved the physical properties of the compounds while retaining good in vitro potency. This exploration led to the discovery of amidopiperidines with improved pharmacokinetic properties. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.09.099

文献信息

• 6H-THIENO[2,3-b]PYRROLE DERIVATIVES AS ANTAGONISTS OF GONADOTROPIN RELEASING HORMONE (GNRH)
  申请人：Foote Michael Kevin

  公开号：US20080045517A1

  公开（公告）日：2008-02-21

  The invention relates to a group of novel thieno-pyrrole compounds of Formula (I): wherein: R 1 , R 2 , R 3 , R 4 and R 5 are as defined in the specification, which are useful as gonadotrophin releasing hormone antagonists. The invention also relates to pharmaceutical formulations of said compounds, methods of treatment using said compounds and to processes for the preparation of said compounds.

  该发明涉及一组新型噻吩-吡咯化合物，其化学式为(I)：其中：R1、R2、R3、R4和R5如规范中所定义，这些化合物可用作促性腺激素释放激素拮抗剂。该发明还涉及该化合物的制药配方、使用该化合物的治疗方法以及制备该化合物的过程。
• 6H-THIEN 2, 3-B]PYRROLE DERIVATIVES AS ANTAGONISTS OF GONADOTROPIN RELEASING HORMONE (GNRH)
  申请人：AstraZeneca AB

  公开号：EP1543012B1

  公开（公告）日：2008-07-16
• US7268158B2
  申请人：——

  公开号：US7268158B2

  公开（公告）日：2007-09-11
• US7547722B2
  申请人：——

  公开号：US7547722B2

  公开（公告）日：2009-06-16
• Synthesis and structure–activity relationships of thieno[2,3-b]pyrroles as antagonists of the GnRH receptor
  作者：Jean Claude Arnould、Bénédicte Delouvrié、Pascal Boutron、Al G. Dossetter、Kevin M. Foote、Annie Hamon、Urs Hancox、Craig S. Harris、Mike Hutton、Maryannick Lamorlette、Zbigniew Matusiak

  DOI：10.1016/j.bmcl.2007.09.099

  日期：2007.12

  A new class of small-molecule GnRH antagonists, the thieno[2,3-b]pyrroles, was designed. Herein, the synthesis and structure-activity relationships are described. Substitution at the C4 position was investigated; during this study, it was observed that introducing piperazines and piperidines improved the physical properties of the compounds while retaining good in vitro potency. This exploration led to the discovery of amidopiperidines with improved pharmacokinetic properties. (c) 2007 Elsevier Ltd. All rights reserved.