(RS)-N-benzyl 2-amino-2-(naphthalen-1-yl)acetamide | 645395-86-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (RS)-N-benzyl 2-amino-2-(naphthalen-1-yl)acetamide
• 英文别名: 2-amino-N-benzyl-2-naphthalen-1-ylacetamide
• CAS: 645395-86-4
• 化学式: C₁₉H₁₈N₂O
• 分子量: 290.365
• InChiKey: YQODCYMYMUSYMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (RS)-N-benzyl 2-amino-2-(naphthalen-1-yl)acetamide 在 盐酸 作用下， 以 乙醚 为溶剂， 以240 mg的产率得到(RS)-N-benzyl 2-amino-2-(naphthalen-1-yl)acetamide hydrochloride
  参考文献：
  名称：

  Synthesis, anticonvulsant activity, and neuropathic pain-attenuating activity of N-benzyl 2-amino-2-(hetero)aromatic acetamides

  摘要：

  N-Benzyl 2-acetamido-2-substituted acetamides, where the 2-substituent is a (hetero) aromatic moiety, are potent anticonvulsants. We report the synthesis and whole animal pharmacological evaluation of 16 analogues where the terminal 2-acetyl group was removed to give the corresponding primary amino acid derivatives (PAADs). Conversion to the PAAD structure led to a substantial drop in seizure protection in animal tests, demonstrating the importance of the N-acetyl moiety for anticonvulsant activity. However, several of the PAADs displayed notable pain-attenuating activities in a mouse model. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.002
• 作为产物：
  描述：

  1-萘乙酸甲酯 在 对甲苯磺酰叠氮 、 [RhCl2(p-cymene)]2 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 、 三氟乙酸 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 68.0h， 生成 (RS)-N-benzyl 2-amino-2-(naphthalen-1-yl)acetamide
  参考文献：
  名称：

  Synthesis, anticonvulsant activity, and neuropathic pain-attenuating activity of N-benzyl 2-amino-2-(hetero)aromatic acetamides

  摘要：

  N-Benzyl 2-acetamido-2-substituted acetamides, where the 2-substituent is a (hetero) aromatic moiety, are potent anticonvulsants. We report the synthesis and whole animal pharmacological evaluation of 16 analogues where the terminal 2-acetyl group was removed to give the corresponding primary amino acid derivatives (PAADs). Conversion to the PAAD structure led to a substantial drop in seizure protection in animal tests, demonstrating the importance of the N-acetyl moiety for anticonvulsant activity. However, several of the PAADs displayed notable pain-attenuating activities in a mouse model. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.002

文献信息

• Amino amides, peptides and peptidomimetics
  申请人：——

  公开号：US20040010162A1

  公开（公告）日：2004-01-15

  Synthetic methods and compounds involving amino amides, peptides and peptidomimetics. Amino amide derivatives are prepared via the one-step three-component reaction of a glyoxamide, an amine, and an organoboron derivative. Conversion of the product to another glyoxamide intermediate allows the iterative use of this chemistry for the synthesis of peptides and peptidomimetics.

  合成方法和涉及氨酰胺、肽和肽类似物的化合物。氨酰胺衍生物是通过一步三组分反应制备的，反应物包括甘氨酰胺、胺和有机硼衍生物。将产物转化为另一种甘氨酰胺中间体，可以迭代地利用这种化学方法合成肽和肽类似物。
• US7247701B2
  申请人：——

  公开号：US7247701B2

  公开（公告）日：2007-07-24
• Synthesis, anticonvulsant activity, and neuropathic pain-attenuating activity of N-benzyl 2-amino-2-(hetero)aromatic acetamides
  作者：Pranjal K. Baruah、Jason Dinsmore、Amber M. King、Christophe Salomé、Marc De Ryck、Rafal Kaminski、Laurent Provins、Harold Kohn

  DOI：10.1016/j.bmc.2012.04.002

  日期：2012.6

  N-Benzyl 2-acetamido-2-substituted acetamides, where the 2-substituent is a (hetero) aromatic moiety, are potent anticonvulsants. We report the synthesis and whole animal pharmacological evaluation of 16 analogues where the terminal 2-acetyl group was removed to give the corresponding primary amino acid derivatives (PAADs). Conversion to the PAAD structure led to a substantial drop in seizure protection in animal tests, demonstrating the importance of the N-acetyl moiety for anticonvulsant activity. However, several of the PAADs displayed notable pain-attenuating activities in a mouse model. (C) 2012 Elsevier Ltd. All rights reserved.