3-azido-1-phenylpropylamine | 1620488-61-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-azido-1-phenylpropylamine
• 英文别名: 3-azido-1-phenylpropan-1-amine
• CAS: 1620488-61-0
• 化学式: C₉H₁₂N₄
• 分子量: 176.221
• InChiKey: YJZBBDZRGUXYGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  74.78
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-azido-1-phenylpropylamine 在 铜 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 生成 N-(3-(4-cyclopentyl-1H-1,2,3-triazol-1-yl)-1-phenylpropyl)-2-hydroxyiminoacetamide
  参考文献：
  名称：

  Design and synthesis of N-substituted-2-hydroxyiminoacetamides and interactions with cholinesterases

  摘要：

  Within this study, we designed and synthesized four new oxime compounds of the N-substituted 2-hydroxyiminoacetamide structure and evaluated their interactions with acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). Our aim was to explore the possibility of extending the dual-binding mode of interaction between the enzyme and the inhibitor to a so-called triple-binding mode of interaction through the introduction of an additional binding moiety. N-substituted 2-hydroxyiminoacetamide 1 was prepared via BOP catalyzed amidation of hydroxyiminoacetic acid with 3-azido-1-phenylpropylamine. An azide group enabled us to prepare more elaborate structures 2-4 by the copper-catalyzed azide-alkyne cycloaddition. The new compounds 1-4 differed in their presumed AChE peripheral site binding moiety, which ranged from an azide group to functionalized heterocycles. Molecular docking studies revealed that all three binding moieties are involved in the non-covalent interactions with ChEs for all of the four compounds, albeit not always in the complete accordance with the proposed hypothesis. All of the four compounds reversibly inhibited the ChEs with their inhibition potency increasing in the same order for both enzymes (1 < 2 < 4 < 3). A higher preference for binding to BChE (K-I from 0.30 mu mol/L to 130 mu mol/L) over AChE (K-I from 50 mmol/L to 1200 mmol/L) was observed for all of the compounds. Compounds were screened for reactivation of cyclosarin-, sarin-and VX-inhibited AChE and BChE. (C) 2016 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.cbi.2016.05.035
• 作为产物：
  描述：

  1-苯基-2-丙烯基胺 在 叠氮磷酸二苯酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 9-硼双环[3.3.1]壬烷 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 生成 3-azido-1-phenylpropylamine
  参考文献：
  名称：

  Enzyme-catalyzed cascade synthesis of hydroxyiminoacetamides

  摘要：

  In order to synthesize N-(3-azido-1-phenylpropyl)-2-hydroxyiminoacetamide, a key compound for the preparation of acetylcholinesterase (AChE) reactivators of the N-substituted 2-hydroxyiminoacetamide type, it was necessary to develop a method for forming an amide bond between an ethyl glyoxylate oxime and an amine. Using Candida antarctica lipase B (CAL-B) in a cascade enzyme-BOP catalyzed reaction, the efficient synthesis of the target hydroxyiminoacetamide was achieved. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.06.027