3-氯-6-[4-(2-氯-5-氟苯氧基)哌啶-1-基]哒嗪 | 944808-82-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-氯-6-[4-(2-氯-5-氟苯氧基)哌啶-1-基]哒嗪
• 英文名称: 3-chloro-6-[4-(2-chloro-5-fluorophenoxy)piperidin-1-yl]pyridazine
• CAS: 944808-82-6
• 化学式: C₁₅H₁₄Cl₂FN₃O
• 分子量: 342.2
• InChiKey: LTGGMHAKSMHHPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-氯-6-[4-(2-氯-5-氟苯氧基)哌啶-1-基]哒嗪 在 [1,1'-bis(diphenylphosphino)ferrocene]PdCl₂(II)*CH₂Cl₂ sodium hydroxide 作用下， 以 甲醇 为溶剂， 25.0~100.0 ℃ 、1.38 MPa 条件下， 反应 6.0h， 生成 6-[4-(2-chloro-5-fluorophenoxy)piperidin-1-yl]pyridazine-3-carboxylic acid
  参考文献：
  名称：

  Discovery of Potent, Selective, Orally Bioavailable Stearoyl-CoA Desaturase 1 Inhibitors

  摘要：

  Stearoyl-CoA desaturase 1 (SCD1) catalyzes the committed step in the biosynthesis of monounsaturated fatty acids from saturated, long-chain fatty acids. Studies with SCD1 knockout mice have established that these animals are lean and protected from leptin deficiency-induced and diet-induced obesity, with greater whole body insulin sensitivity than wild-type animals. In this work, we have discovered a series of potent, selective, orally bioavailable SCD1 inhibitors based on a known pyridazine carboxamide template. The representative lead inhibitor 28c also demonstrates excellent cellular activity in blocking the conversion of saturated long-chain fatty acid-CoAs (LCFA-CoAs) to monounsaturated LCFA-CoAs in HepG2 cells.

  DOI：

  10.1021/jm070219p
• 作为产物：
  描述：

  2-氯-5-氟苯酚 、 1-(6-氯哒嗪-3-基)-4-羟基哌啶 在 偶氮二甲酸二叔丁酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以51%的产率得到3-氯-6-[4-(2-氯-5-氟苯氧基)哌啶-1-基]哒嗪
  参考文献：
  名称：

  Discovery of Potent, Selective, Orally Bioavailable Stearoyl-CoA Desaturase 1 Inhibitors

  摘要：

  Stearoyl-CoA desaturase 1 (SCD1) catalyzes the committed step in the biosynthesis of monounsaturated fatty acids from saturated, long-chain fatty acids. Studies with SCD1 knockout mice have established that these animals are lean and protected from leptin deficiency-induced and diet-induced obesity, with greater whole body insulin sensitivity than wild-type animals. In this work, we have discovered a series of potent, selective, orally bioavailable SCD1 inhibitors based on a known pyridazine carboxamide template. The representative lead inhibitor 28c also demonstrates excellent cellular activity in blocking the conversion of saturated long-chain fatty acid-CoAs (LCFA-CoAs) to monounsaturated LCFA-CoAs in HepG2 cells.

  DOI：

  10.1021/jm070219p