4-(bromomethylcarbonyl)amino-4-methylcarbamoyl-N-Cbz-piperidine | 263388-09-6

• 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: 4-(bromomethylcarbonyl)amino-4-methylcarbamoyl-N-Cbz-piperidine
• 英文别名: Benzyl 4-[(2-bromoacetyl)amino]-4-(methylcarbamoyl)piperidine-1-carboxylate
• CAS: 263388-09-6
• 化学式: C₁₇H₂₂BrN₃O₄
• 分子量: 412.283
• InChiKey: YWMIPCFOXRLULT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  87.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(bromomethylcarbonyl)amino-4-methylcarbamoyl-N-Cbz-piperidine 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 4-(3-morpholinone-4-yl)-4-methylcarbamoyl-1-Cb1-piperidine
  参考文献：
  名称：

  Design, Synthesis, and SAR of Tachykinin Antagonists:  Modulation of Balance in NK₁/NK₂ Receptor Antagonist Activity

  摘要：

  Through optimization of compounds based on the dual NK1/NK2 antagonist ZD6021, it was found that alteration of two key regions could modulate the balance of NK1 and NK2 potency. Substitution of the 2-naphthalene position in analogues of ZD6021 resulted in increased NK1 potency and thus afforded NK1 preferential antagonists. Alterations of the piperidine region could then increase NK2 potency to restore dual NK1/NK2 selectivity. Through these efforts, three novel receptor antagonists from a single chemically related series were identified; two are dual NK1/NK2 antagonists, and the third is an NK1 preferential antagonist. In this paper, the factors affecting the balance of NK1 and NK2 selectivity in this series are discussed and the in vitro and in vivo properties of the novel antagonists are described.

  DOI：

  10.1021/jm020094i
• 作为产物：
  描述：

  4-amino-4-methylcarbamoyl-N-Cbz-piperidine 、 溴乙酰溴 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 4-(bromomethylcarbonyl)amino-4-methylcarbamoyl-N-Cbz-piperidine
  参考文献：
  名称：

  Design, Synthesis, and SAR of Tachykinin Antagonists:  Modulation of Balance in NK₁/NK₂ Receptor Antagonist Activity

  摘要：

  Through optimization of compounds based on the dual NK1/NK2 antagonist ZD6021, it was found that alteration of two key regions could modulate the balance of NK1 and NK2 potency. Substitution of the 2-naphthalene position in analogues of ZD6021 resulted in increased NK1 potency and thus afforded NK1 preferential antagonists. Alterations of the piperidine region could then increase NK2 potency to restore dual NK1/NK2 selectivity. Through these efforts, three novel receptor antagonists from a single chemically related series were identified; two are dual NK1/NK2 antagonists, and the third is an NK1 preferential antagonist. In this paper, the factors affecting the balance of NK1 and NK2 selectivity in this series are discussed and the in vitro and in vivo properties of the novel antagonists are described.

  DOI：

  10.1021/jm020094i