2-甲基-2-丙基[1-(5-溴-2-甲氧基苯基)乙基]氨基甲酸酯 | 701939-03-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-甲基-2-丙基[1-(5-溴-2-甲氧基苯基)乙基]氨基甲酸酯
• 英文名称: (S)-[1-(5-bromo-2-methoxyphenyl)ethyl]carbamic acid tert-butyl ester
• 英文别名: Tert-butyl [(1S)-1-(5-bromo-2-methoxyphenyl)ethyl]carbamate；tert-butyl N-[(1S)-1-(5-bromo-2-methoxyphenyl)ethyl]carbamate
• CAS: 701939-03-9
• 化学式: C₁₄H₂₀BrNO₃
• 分子量: 330.222
• InChiKey: NDRKPQMJMFDZGI-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-甲基-2-丙基[1-(5-溴-2-甲氧基苯基)乙基]氨基甲酸酯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三氟乙酸 、 2-(二叔丁基膦)联苯 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 20.0h， 生成 (S)-1-(2-methoxy-5-morpholin-4-ylphenyl)ethylamine
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship of Acrylamides as KCNQ2 Potassium Channel Openers

  摘要：

  A new class of acrylamides was synthesized, and the effects of these analogues on outward potassium current were evaluated by using two electrode voltage clamp recordings from Xenopus laevis oocytes expressing cloned mKCNQ2 channels. SAR studies indicated that the pharmacophore of the acrylamide series includes the (S) absolute configuration at the (1-phenyl)ethyl moiety and the alpha,beta-unsaturated acrylamide functionality with a free NH. This study identified (S)-N-[1-(3-morpholin-4-yl-phenyl)-ethyl]-3-phenyl-acrylamide ((S)-1) and (S)-N-[1-(4-fluoro-3morpholin-4-yl-phenyl)-ethyl]-3-(4-fluoro-phenyl)-acrylamide ((S)-2) as KCNQ2 openers for further electrophysiological evaluations. These two acrylamides demonstrated significant activity in the cortical spreading depression model of migraine as we reported previously.

  DOI：

  10.1021/jm0305826
• 作为产物：
  描述：

  (S)-1-(2-甲氧苯基)乙胺 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 20.0h， 生成 2-甲基-2-丙基[1-(5-溴-2-甲氧基苯基)乙基]氨基甲酸酯
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship of Acrylamides as KCNQ2 Potassium Channel Openers

  摘要：

  A new class of acrylamides was synthesized, and the effects of these analogues on outward potassium current were evaluated by using two electrode voltage clamp recordings from Xenopus laevis oocytes expressing cloned mKCNQ2 channels. SAR studies indicated that the pharmacophore of the acrylamide series includes the (S) absolute configuration at the (1-phenyl)ethyl moiety and the alpha,beta-unsaturated acrylamide functionality with a free NH. This study identified (S)-N-[1-(3-morpholin-4-yl-phenyl)-ethyl]-3-phenyl-acrylamide ((S)-1) and (S)-N-[1-(4-fluoro-3morpholin-4-yl-phenyl)-ethyl]-3-(4-fluoro-phenyl)-acrylamide ((S)-2) as KCNQ2 openers for further electrophysiological evaluations. These two acrylamides demonstrated significant activity in the cortical spreading depression model of migraine as we reported previously.

  DOI：

  10.1021/jm0305826

文献信息

• Synthesis and Structure−Activity Relationship of Acrylamides as KCNQ2 Potassium Channel Openers
  作者：Yong-Jin Wu、Huan He、Li-Qiang Sun、Alexandre L'Heureux、Jie Chen、Pierre Dextraze、John E. Starrett,、Christopher G. Boissard、Valentin K. Gribkoff、Joanne Natale、Steven I. Dworetzky

  DOI：10.1021/jm0305826

  日期：2004.5.1

  A new class of acrylamides was synthesized, and the effects of these analogues on outward potassium current were evaluated by using two electrode voltage clamp recordings from Xenopus laevis oocytes expressing cloned mKCNQ2 channels. SAR studies indicated that the pharmacophore of the acrylamide series includes the (S) absolute configuration at the (1-phenyl)ethyl moiety and the alpha,beta-unsaturated acrylamide functionality with a free NH. This study identified (S)-N-[1-(3-morpholin-4-yl-phenyl)-ethyl]-3-phenyl-acrylamide ((S)-1) and (S)-N-[1-(4-fluoro-3morpholin-4-yl-phenyl)-ethyl]-3-(4-fluoro-phenyl)-acrylamide ((S)-2) as KCNQ2 openers for further electrophysiological evaluations. These two acrylamides demonstrated significant activity in the cortical spreading depression model of migraine as we reported previously.