2-(4-Aminomethyl-phenyl)-N-methyl-N-((S)-1-phenyl-2-pyrrolidin-1-yl-ethyl)-acetamide | 808753-20-0

• 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: 2-(4-Aminomethyl-phenyl)-N-methyl-N-((S)-1-phenyl-2-pyrrolidin-1-yl-ethyl)-acetamide
• 英文别名: 2-[4-(aminomethyl)phenyl]-N-methyl-N-[(1S)-1-phenyl-2-pyrrolidin-1-ylethyl]acetamide
• CAS: 808753-20-0
• 化学式: C₂₂H₂₉N₃O
• 分子量: 351.492
• InChiKey: IUANQSFTMZCPED-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  49.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-Aminomethyl-phenyl)-N-methyl-N-((S)-1-phenyl-2-pyrrolidin-1-yl-ethyl)-acetamide 、 异氰酸甲酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到N-Methyl-2-{4-[(3-methyl-ureido)-methyl]-phenyl}-N-((S)-1-phenyl-2-pyrrolidin-1-yl-ethyl)-acetamide
  参考文献：
  名称：

  Arylacetamide κ opioid receptor agonists with reduced cytochrome P450 2D6 inhibitory activity

  摘要：

  Some K opioid receptor agonists of the arylacetamide class, for example, ICI 199441 (1), were found to strongly inhibit the activity of cytochrome P450 2D6 (CYP2D6) (1: CYP2D6 IC50 = 26 nM). Certain analogs bearing a substituted sulfonylamino group, for example, 13, were discovered to have significantly reduced CYP2D6 inhibitory activity (13: CYP2D6 IC50 > 10 mu M) while displaying high affinity toward the cloned human K opioid receptor, good kappa/delta and kappa/mu selectivity, and potent in vitro and in vivo agonist activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.020
• 作为产物：
  描述：

  P-氰基苯乙酸甲酯 在 palladium on activated charcoal 盐酸 、 lithium hydroxide 、 氢气 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙腈 为溶剂， 25.0 ℃ 、482.63 kPa 条件下， 生成 2-(4-Aminomethyl-phenyl)-N-methyl-N-((S)-1-phenyl-2-pyrrolidin-1-yl-ethyl)-acetamide
  参考文献：
  名称：

  Arylacetamide κ opioid receptor agonists with reduced cytochrome P450 2D6 inhibitory activity

  摘要：

  Some K opioid receptor agonists of the arylacetamide class, for example, ICI 199441 (1), were found to strongly inhibit the activity of cytochrome P450 2D6 (CYP2D6) (1: CYP2D6 IC50 = 26 nM). Certain analogs bearing a substituted sulfonylamino group, for example, 13, were discovered to have significantly reduced CYP2D6 inhibitory activity (13: CYP2D6 IC50 > 10 mu M) while displaying high affinity toward the cloned human K opioid receptor, good kappa/delta and kappa/mu selectivity, and potent in vitro and in vivo agonist activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.020

文献信息

• Arylacetamide κ opioid receptor agonists with reduced cytochrome P450 2D6 inhibitory activity
  作者：Bertrand Le Bourdonnec、Christopher W. Ajello、Pamela R. Seida、Roberta G. Susnow、Joel A. Cassel、Serge Belanger、Gabriel J. Stabley、Robert N. DeHaven、Diane L. DeHaven-Hudkins、Roland E. Dolle

  DOI：10.1016/j.bmcl.2005.03.020

  日期：2005.5

  Some K opioid receptor agonists of the arylacetamide class, for example, ICI 199441 (1), were found to strongly inhibit the activity of cytochrome P450 2D6 (CYP2D6) (1: CYP2D6 IC50 = 26 nM). Certain analogs bearing a substituted sulfonylamino group, for example, 13, were discovered to have significantly reduced CYP2D6 inhibitory activity (13: CYP2D6 IC50 > 10 mu M) while displaying high affinity toward the cloned human K opioid receptor, good kappa/delta and kappa/mu selectivity, and potent in vitro and in vivo agonist activity. (c) 2005 Elsevier Ltd. All rights reserved.