[4-(chloromethyl)phenyl]-[(3S)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methanone | 949928-25-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [4-(chloromethyl)phenyl]-[(3S)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methanone
• CAS: 949928-25-0
• 化学式: C₁₆H₂₁ClN₂O
• 分子量: 292.809
• InChiKey: ZAKITRAMZBSNSN-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  吲哚 、 [4-(chloromethyl)phenyl]-[(3S)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methanone 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 (3'S)-1'-[4-(1H-indol-1-ylmethyl)benzoyl]-1,3'-bipyrrolidine
  参考文献：
  名称：

  Benzimidazole- and indole-substituted 1,3′-bipyrrolidine benzamides as histamine H3 receptor antagonists

  摘要：

  Using a focused screen of biogenic amine compounds we identified a novel series of H3R antagonists. A preliminary SAR study led to reduction of MW while increasing binding affinity and potency. Optimization of the physical properties of the series led to (S)-6n, with improved brain to plasma exposure and efficacy in both water intake and novel object recognition models. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.122
• 作为产物：
  描述：

  (3'S)-1,3'-联吡咯烷 、 4-氯甲基苯甲酰氯 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 [4-(chloromethyl)phenyl]-[(3S)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methanone
  参考文献：
  名称：

  Benzimidazole- and indole-substituted 1,3′-bipyrrolidine benzamides as histamine H3 receptor antagonists

  摘要：

  Using a focused screen of biogenic amine compounds we identified a novel series of H3R antagonists. A preliminary SAR study led to reduction of MW while increasing binding affinity and potency. Optimization of the physical properties of the series led to (S)-6n, with improved brain to plasma exposure and efficacy in both water intake and novel object recognition models. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.122

文献信息

• N-substituted-azacyclylamines as histamine-3 antagonists
  申请人：Cole Derek Cecil

  公开号：US20070219240A1

  公开（公告）日：2007-09-20

  The present invention provides a compound of formula I and the use thereof for the treatment of a central nervous system disorder related to or affected by the histamine-3 receptor.

  本发明提供了一种I式化合物及其用于治疗与或受到组胺-3受体相关的中枢神经系统疾病的用途。
• US7820825B2
  申请人：——

  公开号：US7820825B2

  公开（公告）日：2010-10-26
• [EN] N-SUBSTITUTED-AZACYCLYLAMINES AS HISTAMINE-3 ANTAGONISTS<br/>[FR] AZACYCLYLAMINES AVEC SUBSTITUTION N EN TANT QU'ANTAGONISTES DE L'HISTAMINE-3
  申请人：WYETH CORP

  公开号：WO2007108936A2

  公开（公告）日：2007-09-27

  [EN] The present invention provides a compound of formula (I) and the use thereof for the treatment of a central nervous system disorder related to or affected by the histamine-3 receptor.
  [FR] La présente invention concerne un composé de formule (I) et son utilisation pour le traitement d'un trouble du système nerveux central lié au récepteur de l'histamine-3 ou influencé par lui.
• Benzimidazole- and indole-substituted 1,3′-bipyrrolidine benzamides as histamine H3 receptor antagonists
  作者：Derek C. Cole、Jonathan L. Gross、Thomas A. Comery、Suzan Aschmies、Warren D. Hirst、Cody Kelley、Ji-In Kim、Katie Kubek、Xiaoping Ning、Brian J. Platt、Albert J. Robichaud、William R. Solvibile、Joseph R. Stock、Gregory Tawa、Marla J. Williams、John W. Ellingboe

  DOI：10.1016/j.bmcl.2009.11.122

  日期：2010.2

  Using a focused screen of biogenic amine compounds we identified a novel series of H3R antagonists. A preliminary SAR study led to reduction of MW while increasing binding affinity and potency. Optimization of the physical properties of the series led to (S)-6n, with improved brain to plasma exposure and efficacy in both water intake and novel object recognition models. (C) 2009 Elsevier Ltd. All rights reserved.