4-[benzyl-(2-naphthylmethyl)-amino]-butyronitrile | 1190600-97-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-[benzyl-(2-naphthylmethyl)-amino]-butyronitrile
• 英文别名: 4-[Benzyl(naphthalen-2-ylmethyl)amino]butanenitrile
• CAS: 1190600-97-5
• 化学式: C₂₂H₂₂N₂
• 分子量: 314.43
• InChiKey: LUOWOCACBZBWAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[benzyl-(2-naphthylmethyl)-amino]-butyronitrile 在 盐酸 作用下， 反应 0.03h， 生成 4-[benzyl-(2-naphthylmethyl)-amino]-butyronitrile hydrochloride
  参考文献：
  名称：

  Allosteric Functional Switch of Neurokinin A-Mediated Signaling at the Neurokinin NK2 Receptor: Structural Exploration

  摘要：

  The neurokinin NK2 receptor is known to pre-exist in equilibrium between at least three states: resting-inactive, calcium-triggering, and cAMP-producing. Its endogeneous ligand, NKA, mainly induces the calcium response. Using a FRET-based assay, we have previously discovered an allosteric modulator of the NK2 receptor that has the unique ability to discriminate among the two signaling pathways: calcium-signaling is not affected while CAMP signaling is significantly decreased. A series of compounds have been prepared and studied in order to better understand the structural determinants of this allosteric functional switch of a GPCR. Most of them display the same allosteric profile, with smooth pharmacomodulation. One compound however exhibits significantly improved modulatory properties of NKA induced signaling when compared to the original modulator.

  DOI：

  10.1021/jm900671k
• 作为产物：
  描述：

  N-benzyl-1-(naphthalen-2-yl)methanamine 、 4-溴丁腈 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以63%的产率得到4-[benzyl-(2-naphthylmethyl)-amino]-butyronitrile
  参考文献：
  名称：

  Allosteric Functional Switch of Neurokinin A-Mediated Signaling at the Neurokinin NK2 Receptor: Structural Exploration

  摘要：

  The neurokinin NK2 receptor is known to pre-exist in equilibrium between at least three states: resting-inactive, calcium-triggering, and cAMP-producing. Its endogeneous ligand, NKA, mainly induces the calcium response. Using a FRET-based assay, we have previously discovered an allosteric modulator of the NK2 receptor that has the unique ability to discriminate among the two signaling pathways: calcium-signaling is not affected while CAMP signaling is significantly decreased. A series of compounds have been prepared and studied in order to better understand the structural determinants of this allosteric functional switch of a GPCR. Most of them display the same allosteric profile, with smooth pharmacomodulation. One compound however exhibits significantly improved modulatory properties of NKA induced signaling when compared to the original modulator.

  DOI：

  10.1021/jm900671k

文献信息

• Allosteric Functional Switch of Neurokinin A-Mediated Signaling at the Neurokinin NK2 Receptor: Structural Exploration
  作者：Céline Valant、Emeline Maillet、Jean-Jacques Bourguignon、Bernard Bucher、Valérie Utard、Jean-Luc Galzi、Marcel Hibert

  DOI：10.1021/jm900671k

  日期：2009.10.8

  The neurokinin NK2 receptor is known to pre-exist in equilibrium between at least three states: resting-inactive, calcium-triggering, and cAMP-producing. Its endogeneous ligand, NKA, mainly induces the calcium response. Using a FRET-based assay, we have previously discovered an allosteric modulator of the NK2 receptor that has the unique ability to discriminate among the two signaling pathways: calcium-signaling is not affected while CAMP signaling is significantly decreased. A series of compounds have been prepared and studied in order to better understand the structural determinants of this allosteric functional switch of a GPCR. Most of them display the same allosteric profile, with smooth pharmacomodulation. One compound however exhibits significantly improved modulatory properties of NKA induced signaling when compared to the original modulator.