3-(4)-dimethylaminobenzylidene anabaseine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-(4)-dimethylaminobenzylidene anabaseine
• 英文别名: (E)-3-(3-(4-dimethylaminobenzylidene)-3,4,5,6-tetrahydropyridin-2-yl)pyridine；VUF10907；3-(4-Dimethylaminobenzylidene)anabaseine；N,N-dimethyl-4-[(E)-(6-pyridin-3-yl-3,4-dihydro-2H-pyridin-5-ylidene)methyl]aniline
• 化学式: C₁₉H₂₁N₃
• 分子量: 291.396
• InChiKey: KHUUTHZSRXABAC-DTQAZKPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  28.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-amino-1-(pyridin-3-yl)pentan-1-one dihydrobromide 、 对二甲氨基苯甲醛 在 sodium acetate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 以36%的产率得到3-(4)-dimethylaminobenzylidene 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

• Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, pyrazolopyridines, isothiazolopyridines, and preparation and uses thereof
  申请人：Schumacher Richard

  公开号：US20070078147A1

  公开（公告）日：2007-04-05

  The present invention relates generally to the field of ligands for nicotinic acetylcholine receptors (nACh receptors), activation of nACh receptors, and the treatment of disease conditions associated with defective or malfunctioning nicotinic acetylcholine receptors, especially of the brain. Further, this invention relates to novel compounds (e.g., indazoles and benzothiazoles), which act as ligands for the α7 nACh receptor subtype, methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.

  本发明一般涉及烟碱乙酰胆碱受体（nACh受体）的配体、nACh受体的激活，以及与缺陷或功能失调的烟碱乙酰胆碱受体相关的疾病状况的治疗，特别是大脑的疾病状况。此外，本发明涉及作为α7 nACh受体亚型的配体的新化合物（例如，吲唑和苯并噻唑），制备这种化合物的方法，含有这种化合物的组合物，以及这些化合物的使用方法。
• Indoles, 1h-indazoles, 1,2-benzisoxazoles, 1,2-benzoisothiazoles, and preparation and uses thereof
  申请人：Xie Wenge

  公开号：US20050250808A1

  公开（公告）日：2005-11-10

  The present invention relates generally to the field of ligands for nicotinic acetylcholine receptors (nACh receptors), activation of nACh receptors, and the treatment of disease conditions associated with defective or malfunctioning nicotinic acetylcholine receptors, especially of the brain. Further, this invention relates to novel compounds (indazoles and benzothiazoles), which act as ligands for the α7 nACh receptor subtype, methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.

  本发明一般涉及尼古丁型乙酰胆碱受体（nACh受体）的配体领域，nACh受体的激活，以及与缺陷或功能异常的尼古丁型乙酰胆碱受体相关的疾病状况的治疗，尤其是大脑的治疗。此外，本发明涉及新型化合物（吲唑和苯并噻唑），其作为α7 nACh受体亚型的配体，制备此类化合物的方法，含有此类化合物的组合物，以及使用这些方法。
• [EN] ANABASEINE DERIVATIVES USEFUL IN THE TREATMENT OF NEURODEGENERATIVE DISEASES<br/>[FR] DERIVES D'ANABASEINE UTILES POUR LE TRAITEMENT DE MALADIES NEURODEGENERATIVES
  申请人：MEMORY PHARM CORP

  公开号：WO2004019943A1

  公开（公告）日：2004-03-11

  The compounds of the present invention are of formula (I): wherein A, R3, R4 is as defined herein, are useful as ligands for nicotinic receptors.

  本发明的化合物的化学式为（I）：其中A、R3、R4如本文所定义，可用作尼古丁受体的配体。
• [EN] ANABASEINE DERIVATIVES USEFUL IN THE TREATMENT OF DEGENERATIVE DISEASES OF THE NERVOUS SYSTEM<br/>[FR] DERIVES D'ANABASEINE UTILISES DANS LE TRAITEMENT DE TROUBLES DEGENERATIFS DU SYSTEME NERVEUX
  申请人：UNIVERSITY OF FLORIDA

  公开号：WO1994005288A1

  公开（公告）日：1994-03-17

  (EN) Novel anabaseine and anabasine derivatives are useful for stimulating brain cholinergic transmission, and have utility in the treatment of degenerative diseases of the nervous system.(FR) De nouveaux dérivés d'anabaséine et d'anabasine peuvent être utilisés pour stimuler la transmission cholinergique dans le cerveau, et pour traiter des troubles dégénératifs du système nerveux.

  （EN）新型的anabaseine和anabasine衍生物可用于刺激大脑胆碱能传递，并在治疗神经系统退行性疾病方面具有用途。 （FR）新型anabaséine和anabasine衍生物可用于刺激大脑胆碱能传递，并用于治疗神经系统的退行性疾病。
• Heterocyclic compounds, methods for the preparation thereof, and uses thereof
  申请人：MEMORY PHARMACEUTICALS CORP.

  公开号：US20040229868A1

  公开（公告）日：2004-11-18

  The compounds of the present invention are of formula I: 1 wherein A, R 3 , R 4 is as defined herein, are useful as ligands for nicotinic receptors.

  本发明的化合物的化学式为I:1，其中A、R3、R4如本文所定义，可用作尼古丁受体的配体。