5-fluoro-2-methoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamide | 90183-19-0

• 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: 5-fluoro-2-methoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamide
• 英文别名: N-(1-Azabicyclo[2.2.2]octan-3-yl)-5-fluoro-2-methoxybenzamide
• CAS: 90183-19-0
• 化学式: C₁₅H₁₉FN₂O₂
• 分子量: 278.326
• InChiKey: LTOBYSGFQRWDCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-氟-2-甲氧基苯甲酸 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 3.5h， 生成 5-fluoro-2-methoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamide
  参考文献：
  名称：

  Synthesis and 5-HT-3 receptor binding activity of 5-[125I]iodo-2,3-dimethoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamide and its 5-halogen-2-alkoxyl homologues

  摘要：

  (S)-5-Iodo-2,3-dimethoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamide (MIZAC) was prepared from 5-iodo-2,3-dimethoxybenzoyl chloride and (S)-3-aminoquinuclidine. [I-125]Iodode-stannylation of its corresponding 5-tri-n-butyltin derivative gave [I-125]-MIZAC at 1800 Ci/mmol. Binding of [I-125]-MIZAC in rat entorhinal cortex revealed a K-D of 1.37 +/- 0.21 nM. A series of racemic 2-O-alkyl derivatives of MIZAC were prepared and 5-HT-3 receptor affinities were determined by inhibition of [I-125]-MIZAC binding. Optimal affinity for the receptor was obtained with small, electron-withdrawing substituents in the aromatic 5-position and with bulky substituents in the 3-position. [I-125]-MIZAC is a selective radioligand useful for in vitro identification of the 5-HT-3 receptor.

  DOI：

  10.1016/s0223-5234(97)81676-5

文献信息

• NOVEL CHIMERIC LIGAND-GATED ION CHANNELS AND METHODS OF USE THEREOF
  申请人：Howard Hughes Medical Institute

  公开号：EP2344636B1

  公开（公告）日：2017-12-06
• US8435762B2
  申请人：——

  公开号：US8435762B2

  公开（公告）日：2013-05-07
• [EN] NOVEL CHIMERIC LIGAND-GATED ION CHANNELS AND METHODS OF USE THEREOF<br/>[FR] CANAUX IONIQUES CHIMÉRIQUES INÉDITS ACTIVÉS PAR LA FIXATION D'UN LIGAND ET LEURS PROCÉDÉS D'UTILISATION
  申请人：HUGHES HOWARD MED INST

  公开号：WO2010042799A2

  公开（公告）日：2010-04-15

  The present invention provides novel chimeric receptors that have unique pharmacology. In particular, the chimeric receptors comprise a mutated ligand binding domain of the α7 nicotinic acetylcholine receptor fused to a transmembrane or channel domain from a ligand-gated ion channel protein. The mutations in the ligand binding domain confer selective binding of compounds. Methods of using the novel chimeric receptors of the invention as well as compounds that preferentially bind and activate the chimeric receptors are also disclosed.
• Synthesis and 5-HT-3 receptor binding activity of 5-[125I]iodo-2,3-dimethoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamide and its 5-halogen-2-alkoxyl homologues
  作者：T de Paulis、WA Hewlett、DE Schmidt、NS Mason、BL Trivedi、MH Ebert

  DOI：10.1016/s0223-5234(97)81676-5

  日期：1997.5

  (S)-5-Iodo-2,3-dimethoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamide (MIZAC) was prepared from 5-iodo-2,3-dimethoxybenzoyl chloride and (S)-3-aminoquinuclidine. [I-125]Iodode-stannylation of its corresponding 5-tri-n-butyltin derivative gave [I-125]-MIZAC at 1800 Ci/mmol. Binding of [I-125]-MIZAC in rat entorhinal cortex revealed a K-D of 1.37 +/- 0.21 nM. A series of racemic 2-O-alkyl derivatives of MIZAC were prepared and 5-HT-3 receptor affinities were determined by inhibition of [I-125]-MIZAC binding. Optimal affinity for the receptor was obtained with small, electron-withdrawing substituents in the aromatic 5-position and with bulky substituents in the 3-position. [I-125]-MIZAC is a selective radioligand useful for in vitro identification of the 5-HT-3 receptor.