(3-benzylidene)anabaseine | 148372-05-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (3-benzylidene)anabaseine
• 英文别名: (E)-3-(3-benzylidene-3,4,5,6-tetrahydropyridin-2-yl)pyridine；VUF10835；3-benzylidene-3,4,5,6-tetrahydro-[2,3']bipyridinyl；3-(Benzylidene)anabaseine；3-[(5E)-5-benzylidene-3,4-dihydro-2H-pyridin-6-yl]pyridine
• CAS: 148372-05-8
• 化学式: C₁₇H₁₆N₂
• 分子量: 248.327
• InChiKey: KRYNRVPZHUUTOR-NTCAYCPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-amino-1-(pyridin-3-yl)pentan-1-one dihydrobromide 、 苯甲醛 在 sodium acetate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 以33%的产率得到(3-benzylidene)anabaseine
  参考文献：
  名称：

  Online Fluorescence Enhancement Assay for the Acetylcholine Binding Protein with Parallel Mass Spectrometric Identification

  摘要：

  The acetylcholine binding protein (AChBP) is considered an analogue for the ligand-binding domain of neuronal nicotinic acetylcholine receptors (nAChRs). Its stability and solubility in aqueous buffer allowed the development of an online bioaffinity analysis system. For this, a tracer ligand which displays enhanced fluorescence in the binding pocket of AChBP was identified from a concise series of synthetic benzylidene anabaseines. Evaluation and optimization of the bioaffinity assay was performed in a convenient microplate reader format and subsequently transferred to the online format. The high reproducibility has the prospect of estimating the affinities of ligands from an in-house drug discovery library injected in one known concentration. Furthermore, the online bioaffinity analysis system could also be applied to mixture analysis by using gradient HPLC. This led to the possibility of affinity ranking of ligands in mixtures with parallel high-resolution mass spectrometry for compound identification.

  DOI：

  10.1021/jm100230k

文献信息

• ANABASINE DERIVATIVES TARGETING THE NICOTINIC ACETYLCHOLINE RECEPTORS
  申请人：University of Florida Research Foundation

  公开号：EP2791135B1

  公开（公告）日：2018-06-06
• US20140343042A1
  申请人：——

  公开号：US20140343042A1

  公开（公告）日：2014-11-20
• US9150558B2
  申请人：——

  公开号：US9150558B2

  公开（公告）日：2015-10-06
• Online Fluorescence Enhancement Assay for the Acetylcholine Binding Protein with Parallel Mass Spectrometric Identification
  作者：Jeroen Kool、Gerdien E. de Kloe、Ben Bruyneel、Jon S. de Vlieger、Kim Retra、Maikel Wijtmans、Rene van Elk、August B. Smit、Rob Leurs、Henk Lingeman、Iwan J.P. de Esch、Hubertus Irth

  DOI：10.1021/jm100230k

  日期：2010.6.24

  The acetylcholine binding protein (AChBP) is considered an analogue for the ligand-binding domain of neuronal nicotinic acetylcholine receptors (nAChRs). Its stability and solubility in aqueous buffer allowed the development of an online bioaffinity analysis system. For this, a tracer ligand which displays enhanced fluorescence in the binding pocket of AChBP was identified from a concise series of synthetic benzylidene anabaseines. Evaluation and optimization of the bioaffinity assay was performed in a convenient microplate reader format and subsequently transferred to the online format. The high reproducibility has the prospect of estimating the affinities of ligands from an in-house drug discovery library injected in one known concentration. Furthermore, the online bioaffinity analysis system could also be applied to mixture analysis by using gradient HPLC. This led to the possibility of affinity ranking of ligands in mixtures with parallel high-resolution mass spectrometry for compound identification.