6-[4-(2-chloro-5-fluorophenoxy)piperidin-1-yl]pyridazine-3-carboxylic acid | 944808-24-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 6-[4-(2-chloro-5-fluorophenoxy)piperidin-1-yl]pyridazine-3-carboxylic acid
• CAS: 944808-24-6
• 化学式: C₁₆H₁₅ClFN₃O₃
• 分子量: 351.765
• InChiKey: OFAMDCLCBNNDTR-UHFFFAOYSA-N

物化性质

• 沸点：
  585.1±50.0 °C(Predicted)
• 密度：
  1.428±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-[4-(2-chloro-5-fluorophenoxy)piperidin-1-yl]pyridazine-3-carboxylic acid 在 氨 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 、 三氯氧磷 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 3-[4-(2-chloro-5-fluorophenoxy)piperidin-1-yl]-6-(5-methyl-1H-1,2,4-triazol-3-yl)pyridazine
  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 在 [1,1'-bis(diphenylphosphino)ferrocene]PdCl₂(II)*CH₂Cl₂ sodium hydroxide 、 偶氮二甲酸二叔丁酯 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 25.0~100.0 ℃ 、1.38 MPa 条件下， 反应 8.0h， 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