ethyl 2-(2-bromo-N-[4-[ethyl(3-methylsulfonylpropyl)amino]-6-methyl-3-nitropyridin-2-yl]-4-propan-2-ylanilino)acetate | 856686-06-1

• 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 2-(2-bromo-N-[4-[ethyl(3-methylsulfonylpropyl)amino]-6-methyl-3-nitropyridin-2-yl]-4-propan-2-ylanilino)acetate
• CAS: 856686-06-1
• 化学式: C₂₅H₃₅BrN₄O₆S
• 分子量: 599.546
• InChiKey: VCJBLIXNTUOXPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  134
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl 2-(2-bromo-N-[4-[ethyl(3-methylsulfonylpropyl)amino]-6-methyl-3-nitropyridin-2-yl]-4-propan-2-ylanilino)acetate 在 盐酸 、 铁粉 作用下， 以 乙醇 为溶剂， 生成 4-(2-bromo-4-isopropylphenyl)-8-[ethyl-(3-methanesulfonylpropyl)amino]-6-methyl-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one
  参考文献：
  名称：

  Synthesis, Structure−Activity Relationships, and in Vivo Properties of 3,4-Dihydro-1H-pyrido[2,3-b]pyrazin-2-ones as Corticotropin-Releasing Factor-1 Receptor Antagonists

  摘要：

  Corticotropin releasing factor (CRF) is the primary regulator of the hypothalamus-pituitary-adrenal (HPA) axis, coordinating the endocrine, behavioral, and autonomic responses to stress. It has been postulated that small molecules that can antagonize the binding of CRF, to its receptor may serve as a treatment for anxiety-related and/or affective disorders. Members within a series of 3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-ones, exemplified by compound 2 (IC50 = 0.70 nM), were found to be very potent antagonists of CRF1. Compound 8w showed high CRF1 receptor binding affinity and was examined further in vivo. The compound was efficacious in a defensive withdrawal model of anxiety in rats and had a long half-life and reasonable oral bioavailability in dog pharmacokinetic studies.

  DOI：

  10.1021/jm049737f
• 作为产物：
  描述：

  4-羟基-6-甲基-3-硝基-2-吡啶醇 在 sodium hydride 、 环己胺 、 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 80.67h， 生成 ethyl 2-(2-bromo-N-[4-[ethyl(3-methylsulfonylpropyl)amino]-6-methyl-3-nitropyridin-2-yl]-4-propan-2-ylanilino)acetate
  参考文献：
  名称：

  Synthesis, Structure−Activity Relationships, and in Vivo Properties of 3,4-Dihydro-1H-pyrido[2,3-b]pyrazin-2-ones as Corticotropin-Releasing Factor-1 Receptor Antagonists

  摘要：

  Corticotropin releasing factor (CRF) is the primary regulator of the hypothalamus-pituitary-adrenal (HPA) axis, coordinating the endocrine, behavioral, and autonomic responses to stress. It has been postulated that small molecules that can antagonize the binding of CRF, to its receptor may serve as a treatment for anxiety-related and/or affective disorders. Members within a series of 3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-ones, exemplified by compound 2 (IC50 = 0.70 nM), were found to be very potent antagonists of CRF1. Compound 8w showed high CRF1 receptor binding affinity and was examined further in vivo. The compound was efficacious in a defensive withdrawal model of anxiety in rats and had a long half-life and reasonable oral bioavailability in dog pharmacokinetic studies.

  DOI：

  10.1021/jm049737f