(S)-2-ethyl-4-(2-methyl-4-propoxyphenyl)piperazine-1-carbonitrile | 1509949-09-0

• 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: (S)-2-ethyl-4-(2-methyl-4-propoxyphenyl)piperazine-1-carbonitrile
• CAS: 1509949-09-0
• 化学式: C₁₇H₂₅N₃O
• 分子量: 287.405
• InChiKey: VWNSIBOOIDGIMA-HNNXBMFYSA-N

物化性质

• 沸点：
  480.4±45.0 °C(predicted)
• 密度：
  1.08±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  39.5
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-2-ethyl-4-(2-methyl-4-propoxyphenyl)piperazine-1-carbonitrile 在 吡啶 、 盐酸羟胺 作用下， 以 乙醇 、 水 为溶剂， 反应 0.42h， 生成 (S)-5-ethyl-3-(2-ethyl-4-(2-methyl-4-propoxyphenyl)piperazin-1-yl)-1,2,4-oxadiazole
  参考文献：
  名称：

  Piperazine Oxadiazole Inhibitors of Acetyl-CoA Carboxylase

  摘要：

  Acetyl-CoA carboxylase (ACC) is a target of interest for the treatment of metabolic syndrome. Starting from a biphenyloxadiazole screening hit, a series of piperazine oxadiazole ACC inhibitors was developed. Initial pharmacokinetic liabilities of the piperazine oxadiazoles were overcome by blocking predicted sites of metabolism, resulting in compounds with suitable properties for further in vivo studies. Compound 26 was shown to inhibit malonyl-CoA production in an in vivo pharmacodynamic assay and was advanced to a long-term efficacy study. Prolonged dosing with compound 26 resulted in impaired glucose tolerance in diet-induced obese (DIO) CS7BL6 mice, an unexpected finding.

  DOI：

  10.1021/jm401601s
• 作为产物：
  描述：

  4-溴-3-甲基苯酚 在 chloro(2-dicyclohexylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) methyl-t-butyl ether adduct 、 caesium carbonate 、 N,N-二异丙基乙胺 、 三氟乙酸 、 sodium t-butanolate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.66h， 生成 (S)-2-ethyl-4-(2-methyl-4-propoxyphenyl)piperazine-1-carbonitrile
  参考文献：
  名称：

  Piperazine Oxadiazole Inhibitors of Acetyl-CoA Carboxylase

  摘要：

  Acetyl-CoA carboxylase (ACC) is a target of interest for the treatment of metabolic syndrome. Starting from a biphenyloxadiazole screening hit, a series of piperazine oxadiazole ACC inhibitors was developed. Initial pharmacokinetic liabilities of the piperazine oxadiazoles were overcome by blocking predicted sites of metabolism, resulting in compounds with suitable properties for further in vivo studies. Compound 26 was shown to inhibit malonyl-CoA production in an in vivo pharmacodynamic assay and was advanced to a long-term efficacy study. Prolonged dosing with compound 26 resulted in impaired glucose tolerance in diet-induced obese (DIO) CS7BL6 mice, an unexpected finding.

  DOI：

  10.1021/jm401601s