[4-bromobenzyl-(2-naphthylmethyl)-amino]-acetonitrile | 634889-07-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [4-bromobenzyl-(2-naphthylmethyl)-amino]-acetonitrile
• 英文别名: 2-[(4-Bromophenyl)methyl-(naphthalen-2-ylmethyl)amino]acetonitrile
• CAS: 634889-07-9
• 化学式: C₂₀H₁₇BrN₂
• 分子量: 365.272
• InChiKey: SDULGMZUGPNQJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (2-naphthylmethyl)-4-bromobenzylamine 、 氯乙腈 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以65%的产率得到[4-bromobenzyl-(2-naphthylmethyl)-amino]-acetonitrile
  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

• Method for isolating an allosteric effector of a receptor
  申请人：Galzi Jean-Luc

  公开号：US20060194259A1

  公开（公告）日：2006-08-31

  A method for isolating an allosteric effector of a receptor, by determining the variation of the dissociation kinetics of the complex formed between the receptor and one of its ligands in the presence of the allosteric effector, as compared to the kinetics dissociation, in the absence of the effector, and/or the amplitude of the linkage formed between the receptor and the ligand in the presence of the allosteric effector, as compared to the amplitude in the absence of the effector. The receptor and ligand are being involved in at least one biological response, and the allosteric effector is capable of modulating at least one of the responses. The receptor is marked by at least one fluorescent protein, and the ligand by a molecule capable of absorbing light, or by a fluorescent substance.

  一种用于分离受体的异位效应物的方法，其方法是确定在存在异位效应物的情况下，受体与其配体之间形成的复合物的解离动力学与不存在效应物时的解离动力学相比的变化，和/或在存在异位效应物的情况下，受体与配体之间形成的联系的振幅与不存在效应物时的振幅相比的变化。受体和配体正在参与至少一种生物反应，而异源效应物能够调节至少一种反应。受体由至少一种荧光蛋白标记，配体由能够吸收光的分子或荧光物质标记。
• PROCEDE D'IDENTIFICATION D'EFFECTEURS ALLOSTERIQUES D'UN RECEPTEUR
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE

  公开号：EP1514112B1

  公开（公告）日：2006-09-06
• 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.