ethyl 2-(piperazin-1-yl)nicotinate hydrochloride | 900183-96-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: ethyl 2-(piperazin-1-yl)nicotinate hydrochloride
• 英文别名: Ethyl 2-(1-piperazinyl)nicotinate hydrochloride, AldrichCPR；ethyl 2-piperazin-1-ylpyridine-3-carboxylate;hydrochloride
• CAS: 900183-96-2
• 化学式: C₁₂H₁₇N₃O₂*ClH
• 分子量: 271.747
• InChiKey: RRDHFBQJJCAUQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.09
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-氯-6-(三氟甲基)-1H-苯并咪唑 、 ethyl 2-(piperazin-1-yl)nicotinate hydrochloride 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 ethyl 2-(4-(6-(Trifluoromethyl)-1H-benzo[d]imidazol-2-yl)-piperazin-1-yl)nicotinate
  参考文献：
  名称：

  Design of Potent, Orally Available Antagonists of the Transient Receptor Potential Vanilloid 1. Structure−Activity Relationships of 2-Piperazin-1-yl-1H-benzimidazoles

  摘要：

  The vanilloid receptor-1 ( VR1 or TRPV1) is a membrane-bound, nonselective cation channel that is predominantly expressed by peripheral neurons sensing painful stimuli. TRPV1 antagonists produce antihyperalgesic effects in animal models of inflammatory and neuropathic pain. Herein, we describe the synthesis and the structure-activity relationships of a series of 2-(4-pyridin-2-ylpiperazin-1-yl)-1H-benzo-[ d] imidazoles as novel TRPV1 antagonists. Compound 46ad was among the most potent analogues in this series. This compound was orally bioavailable in rats and was efficacious in blocking capsaicin-induced flinch in rats in a dose-dependent manner. Compound 46ad also reversed thermal hyperalgesia in a model of inflammatory pain, which was induced by complete Freund's adjuvant ( CFA).

  DOI：

  10.1021/jm060065y
• 作为产物：
  描述：

  2-氯烟酸乙酯 在 盐酸 、 铜 、 potassium carbonate 作用下， 以 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 ethyl 2-(piperazin-1-yl)nicotinate hydrochloride
  参考文献：
  名称：

  Design of Potent, Orally Available Antagonists of the Transient Receptor Potential Vanilloid 1. Structure−Activity Relationships of 2-Piperazin-1-yl-1H-benzimidazoles

  摘要：

  The vanilloid receptor-1 ( VR1 or TRPV1) is a membrane-bound, nonselective cation channel that is predominantly expressed by peripheral neurons sensing painful stimuli. TRPV1 antagonists produce antihyperalgesic effects in animal models of inflammatory and neuropathic pain. Herein, we describe the synthesis and the structure-activity relationships of a series of 2-(4-pyridin-2-ylpiperazin-1-yl)-1H-benzo-[ d] imidazoles as novel TRPV1 antagonists. Compound 46ad was among the most potent analogues in this series. This compound was orally bioavailable in rats and was efficacious in blocking capsaicin-induced flinch in rats in a dose-dependent manner. Compound 46ad also reversed thermal hyperalgesia in a model of inflammatory pain, which was induced by complete Freund's adjuvant ( CFA).

  DOI：

  10.1021/jm060065y