ethyl 3-(2,2-difluoro-2-(2-pyridyl)ethylamino)-6-cyanopyrazin-(1H)-2-one-1-acetate | 312904-97-5

• 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: ethyl 3-(2,2-difluoro-2-(2-pyridyl)ethylamino)-6-cyanopyrazin-(1H)-2-one-1-acetate
• 英文别名: Ethyl 2-[6-cyano-3-[(2,2-difluoro-2-pyridin-2-ylethyl)amino]-2-oxopyrazin-1-yl]acetate
• CAS: 312904-97-5
• 化学式: C₁₆H₁₅F₂N₅O₃
• 分子量: 363.324
• InChiKey: OFZSBUMVHGNIKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 3-(2,2-difluoro-2-(2-pyridyl)ethylamino)-6-cyanopyrazin-(1H)-2-one-1-acetate 在 lithium hydroxide 、 N-羟基-7-氮杂苯并三氮唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 3-fluoro-4-methyl-2-pyridylmethyl 3-(2,2-difluoro-2-(2-pyridyl)ethylamino)-6-cyanopyrazin-2-one-1-acetamide hydrochloride
  参考文献：
  名称：

  Metabolism-Directed Optimization of 3-Aminopyrazinone Acetamide Thrombin Inhibitors. Development of an Orally Bioavailable Series Containing P1 and P3 Pyridines

  摘要：

  Recent efforts in the field of thrombin inhibitor research have focused on the identification of compounds with good oral bioavailability and pharmacokinetics. In this manuscript we describe a metabolism-based approach to the optimization of the 3-(2-phenethylamino)-6-methylpyrazinone acetamide template (e.g., 1) which resulted in the,modification of each of the three principal components (i.e., P1, P2, P3) comprising this series. As a result of these studies, several potent thrombin inhibitors (e.g., 20, 24, 25) were identified which exhibit high levels of oral bioavailability and long plasma half-lives.

  DOI：

  10.1021/jm020311f
• 作为产物：
  描述：

  2-吡啶乙酸乙酯 在 10percent Pd/C sodium tetrahydroborate 、 sodium azide 、 2,6-二叔丁基-4-甲基吡啶 、 氢气 、 双(三甲基硅烷基)氨基钾 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 6.25h， 生成 ethyl 3-(2,2-difluoro-2-(2-pyridyl)ethylamino)-6-cyanopyrazin-(1H)-2-one-1-acetate
  参考文献：
  名称：

  Metabolism-Directed Optimization of 3-Aminopyrazinone Acetamide Thrombin Inhibitors. Development of an Orally Bioavailable Series Containing P1 and P3 Pyridines

  摘要：

  Recent efforts in the field of thrombin inhibitor research have focused on the identification of compounds with good oral bioavailability and pharmacokinetics. In this manuscript we describe a metabolism-based approach to the optimization of the 3-(2-phenethylamino)-6-methylpyrazinone acetamide template (e.g., 1) which resulted in the,modification of each of the three principal components (i.e., P1, P2, P3) comprising this series. As a result of these studies, several potent thrombin inhibitors (e.g., 20, 24, 25) were identified which exhibit high levels of oral bioavailability and long plasma half-lives.

  DOI：

  10.1021/jm020311f