methyl 6-[4-(2-chloro-5-fluorophenoxy)piperidin-1-yl]pyridazine-3-carboxylate | 944808-17-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: methyl 6-[4-(2-chloro-5-fluorophenoxy)piperidin-1-yl]pyridazine-3-carboxylate
• CAS: 944808-17-7
• 化学式: C₁₇H₁₇ClFN₃O₃
• 分子量: 365.792
• InChiKey: JLADNYSWTPDBQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 6-[4-(2-chloro-5-fluorophenoxy)piperidin-1-yl]pyridazine-3-carboxylate 在 sodium hydroxide 、 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 10.0h， 生成 3-[4-（2-氯-5-氟苯氧基）-1-哌啶基]-6-（5-甲基-1,3,4-恶二唑-2-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
• 作为产物：
  描述：

  2-氯-5-氟苯酚 在 [1,1'-bis(diphenylphosphino)ferrocene]PdCl₂(II)*CH₂Cl₂ 偶氮二甲酸二叔丁酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 25.0~100.0 ℃ 、1.38 MPa 条件下， 反应 5.0h， 生成 methyl 6-[4-(2-chloro-5-fluorophenoxy)piperidin-1-yl]pyridazine-3-carboxylate
  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