(S)-[1-(3-morpholin-4-yl-phenyl)ethyl]-carbamic acid tert-butyl ester | 477312-35-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (S)-[1-(3-morpholin-4-yl-phenyl)ethyl]-carbamic acid tert-butyl ester
• 英文别名: tert-butyl (S)-(1-(3-morpholinophenyl)ethyl)carbamate；1,1-dimethylethyl {(1S)-1-[3-(4-morpholinyl)phenyl]ethyl}carbamate；tert-butyl N-[(1S)-1-(3-morpholin-4-ylphenyl)ethyl]carbamate
• CAS: 477312-35-9
• 化学式: C₁₇H₂₆N₂O₃
• 分子量: 306.405
• InChiKey: RKMMBRBUVHVCKY-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  50.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-[1-(3-morpholin-4-yl-phenyl)ethyl]-carbamic acid tert-butyl ester 在 盐酸 、 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (S)-3-(4-Fluoro-phenyl)-N-[1-(3-morpholin-4-yl-phenyl)-ethyl]-acrylamide
  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：

  [(1S)-1-(3-甲氧基苯基)乙基]氨基甲酸叔丁酯 在 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 三溴化硼 、 三乙胺 、 2-(二叔丁基膦)联苯 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 (S)-[1-(3-morpholin-4-yl-phenyl)ethyl]-carbamic acid tert-butyl ester
  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

• [EN] PYRIDAZINE DERIVATIVES FOR INHIBITING BETA AMYLOID PEPTIDE PRODUCTION<br/>[FR] DÉRIVÉS DE PYRIDAZINE POUR INHIBER LA PRODUCTION DE PEPTIDE BÉTA AMYLOÏDE
  申请人：GLAXO GROUP LTD

  公开号：WO2009050227A1

  公开（公告）日：2009-04-23

  The present invention relates to novel compounds that inhibit the production of β- amyloid peptide (1-42), processes for their preparation, to compositions containing them and to their use in the treatment of diseases characterised by elevated β-amyloid levels or β-amyloid deposits, particularly Alzheimer's disease.

  本发明涉及抑制β-淀粉样肽（1-42）产生的新化合物，其制备方法，含有这些化合物的组合物，以及它们在治疗由高β-淀粉样蛋白水平或β-淀粉样蛋白沉积特征的疾病中的用途，特别是阿尔茨海默病。
• Design and development of selective competitive fluorescent ligands for the detection and visualization of Kv7.2/7.3 <i>in vitro</i>
  作者：Zhen Qiao、Siyuan Tang、Jialiang Guan、Zhengji Yin、Chao Zhu、Qiqi Zhou、Liming Shao

  DOI：10.1039/d2cc00372d

  日期：——

  A series of specific and potent fluorescent ligands were developed for labelling and visualizing Kv7.2/7.3 based molecular rotation restriction. Probes 21b and 24a were found to be safe and convenient tools to detect and visualize Kv7.2/7.3 in live cells and mouse brain tissue.

  开发了一系列特异性和有效的荧光配体，用于标记和可视化基于 Kv7.2/7.3 的分子旋转限制。发现探针21b和24a是检测和可视化活细胞和小鼠脑组织中的 Kv7.2/7.3 的安全方便的工具。