biphenyl-4-carboxylic acid {4-[4-(2,4-dimethoxyphenyl)piperazin-1-yl]butyl}amide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: biphenyl-4-carboxylic acid {4-[4-(2,4-dimethoxyphenyl)piperazin-1-yl]butyl}amide
• 英文别名: biphenyl-4-carboxylic acid {4-[4-(2,4-dimethoxy-phenyl)-piperazin-1-yl]-butyl}-amide；Biphenyl-4-carboxylic acid{4-[4-(2,4-dimethoxyphenyl)-piperazin-1-yl]-butyl}amide；N-[4-[4-(2,4-dimethoxyphenyl)piperazin-1-yl]butyl]-4-phenylbenzamide
• 化学式: C₂₉H₃₅N₃O₃
• 分子量: 473.615
• InChiKey: MVSROBKUXHYXAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  54
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-[4-(2,4-dimethoxyphenyl)piperazin-1-yl]butylamine hydrochloride 、 4-苯基苯甲酸 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以85 mg的产率得到biphenyl-4-carboxylic acid {4-[4-(2,4-dimethoxyphenyl)piperazin-1-yl]butyl}amide
  参考文献：
  名称：

  SAR and biological evaluation of SEN12333/WAY-317538: Novel alpha 7 nicotinic acetylcholine receptor agonist

  摘要：

  Alpha 7 nicotinic acetylcholine receptor (alpha(7) nAChR) agonists are promising therapeutic candidates for the treatment of cognitive impairment associated with a variety of disorders including Alzheimer's disease and schizophrenia. Alpha 7 nAChRs are expressed in brain regions associated with cognitive function, regulate cholinergic neurotransmission and have been shown to be down regulated in both schizophrenia and Alzheimer's disease. Herein we report a novel, potent small molecule agonist of the alpha 7 nAChR, SEN12333/WAY-317538. This compound is a selective agonist of the alpha(7) nAChR with excellent in vitro and in vivo profiles, excellent brain penetration and oral bioavailability, and demonstrates in vivo efficacy in multiple behavioural cognition models. The SAR and biological evaluation of this series of compounds are discussed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.05.040

文献信息

• SAR and biological evaluation of SEN12333/WAY-317538: Novel alpha 7 nicotinic acetylcholine receptor agonist
  作者：Simon N. Haydar、Chiara Ghiron、Laura Bettinetti、Hendrick Bothmann、Thomas A. Comery、John Dunlop、Salvatore La Rosa、Iolanda Micco、Martina Pollastrini、Joanna Quinn、Renza Roncarati、Carla Scali、Michela Valacchi、Maurizio Varrone、Riccardo Zanaletti

  DOI：10.1016/j.bmc.2009.05.040

  日期：2009.7

  Alpha 7 nicotinic acetylcholine receptor (alpha(7) nAChR) agonists are promising therapeutic candidates for the treatment of cognitive impairment associated with a variety of disorders including Alzheimer's disease and schizophrenia. Alpha 7 nAChRs are expressed in brain regions associated with cognitive function, regulate cholinergic neurotransmission and have been shown to be down regulated in both schizophrenia and Alzheimer's disease. Herein we report a novel, potent small molecule agonist of the alpha 7 nAChR, SEN12333/WAY-317538. This compound is a selective agonist of the alpha(7) nAChR with excellent in vitro and in vivo profiles, excellent brain penetration and oral bioavailability, and demonstrates in vivo efficacy in multiple behavioural cognition models. The SAR and biological evaluation of this series of compounds are discussed. (C) 2009 Elsevier Ltd. All rights reserved.