(S)-3,5-dichloro-N-isobutyl-N-(pyrrolidin-3-yl)benzamide | 1190739-11-7

• 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: (S)-3,5-dichloro-N-isobutyl-N-(pyrrolidin-3-yl)benzamide
• 英文别名: 3,5-dichloro-N-(2-methylpropyl)-N-[(3S)-pyrrolidin-3-yl]benzamide
• CAS: 1190739-11-7
• 化学式: C₁₅H₂₀Cl₂N₂O
• 分子量: 315.243
• InChiKey: IECZTWNGAWLQAQ-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  tert-butyl (S)-3-(3,5-dichloro-N-isobutylbenzamido)pyrrolidine-1-carboxylate 生成 (S)-3,5-dichloro-N-isobutyl-N-(pyrrolidin-3-yl)benzamide
  参考文献：
  名称：

  N-[(3S)-Pyrrolidin-3-yl]benzamides as novel dual serotonin and noradrenaline reuptake inhibitors: Impact of small structural modifications on P-gp recognition and CNS penetration

  摘要：

  The structure-activity relationship and the synthesis of novel N-[(3S)-pyrrolidin-3-yl]benzamides as dual serotonin and noradrenaline monoamine reuptake inhibitors (SNRI) is described. Preferred compound 9 aka PF-184,298 is a potent SNRI with good selectivity over dopamine reuptake inhibition (DRI), good in vitro metabolic stability, weak CYP inhibition and drug-like physicochemical properties consistent with CNS target space. Evaluation in an in vivo preclinical model of stress urinary incontinence showed 9 significantly increased urethral tone at free plasma concentrations consistent with its in vitro primary pharmacology. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.049

文献信息

• N-[(3S)-Pyrrolidin-3-yl]benzamides as novel dual serotonin and noradrenaline reuptake inhibitors: Impact of small structural modifications on P-gp recognition and CNS penetration
  作者：Florian Wakenhut、Gill A. Allan、Paul V. Fish、M. Jonathan Fray、Anthony C. Harrison、Rachel McCoy、Stephen C. Phillips、Alan Stobie、Dominique Westbrook、Simon L. Westbrook、Gavin A. Whitlock

  DOI：10.1016/j.bmcl.2009.07.049

  日期：2009.9

  The structure-activity relationship and the synthesis of novel N-[(3S)-pyrrolidin-3-yl]benzamides as dual serotonin and noradrenaline monoamine reuptake inhibitors (SNRI) is described. Preferred compound 9 aka PF-184,298 is a potent SNRI with good selectivity over dopamine reuptake inhibition (DRI), good in vitro metabolic stability, weak CYP inhibition and drug-like physicochemical properties consistent with CNS target space. Evaluation in an in vivo preclinical model of stress urinary incontinence showed 9 significantly increased urethral tone at free plasma concentrations consistent with its in vitro primary pharmacology. (C) 2009 Elsevier Ltd. All rights reserved.