5-bromo-N-(cyclohexylmethyl)pyrazin-2-amine | 1040526-32-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-bromo-N-(cyclohexylmethyl)pyrazin-2-amine
• CAS: 1040526-32-6
• 化学式: C₁₁H₁₆BrN₃
• 分子量: 270.172
• InChiKey: LWMYZRCMNBIJBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  37.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-N-(cyclohexylmethyl)pyrazin-2-amine 、 4-硼-L-苯丙氨酸 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.1h， 生成 (S)-2-amino-3-(4-(5-(cyclohexylmethylamino)pyrazin-2-yl)phenyl)propanoic acid
  参考文献：
  名称：

  Modulation of Peripheral Serotonin Levels by Novel Tryptophan Hydroxylase Inhibitors for the Potential Treatment of Functional Gastrointestinal Disorders

  摘要：

  The discovery of a novel class of peripheral tryptophan hydroxylase (TPH) inhibitors is described. This class of TPH inhibitors exhibits excellent potency in in vitro biochemical and cell-based assays, and it selectively reduces serotonin levels in the murine intestine after oral administration without affecting levels in the brain. These TPH1 inhibitors may provide novel treatments for gastrointestinal disorders associated with dysregulation of the serotonergic system, such as chemotherapy-induced emesis and irritable bowel syndrome.

  DOI：

  10.1021/jm800338j
• 作为产物：
  描述：

  2-氨基-5-溴吡嗪 、 溴甲基环己烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以18%的产率得到5-bromo-N-(cyclohexylmethyl)pyrazin-2-amine
  参考文献：
  名称：

  Modulation of Peripheral Serotonin Levels by Novel Tryptophan Hydroxylase Inhibitors for the Potential Treatment of Functional Gastrointestinal Disorders

  摘要：

  The discovery of a novel class of peripheral tryptophan hydroxylase (TPH) inhibitors is described. This class of TPH inhibitors exhibits excellent potency in in vitro biochemical and cell-based assays, and it selectively reduces serotonin levels in the murine intestine after oral administration without affecting levels in the brain. These TPH1 inhibitors may provide novel treatments for gastrointestinal disorders associated with dysregulation of the serotonergic system, such as chemotherapy-induced emesis and irritable bowel syndrome.

  DOI：

  10.1021/jm800338j

文献信息

• Modulation of Peripheral Serotonin Levels by Novel Tryptophan Hydroxylase Inhibitors for the Potential Treatment of Functional Gastrointestinal Disorders
  作者：Zhi-Cai Shi、Arokiasamy Devasagayaraj、Kunjian Gu、Haihong Jin、Brett Marinelli、Lakshman Samala、Sheldon Scott、Terry Stouch、Ashok Tunoori、Ying Wang、Yi Zang、Chengmin Zhang、S. David Kimball、Alan J. Main、Weimei Sun、Qi Yang、Amr Nouraldeen、Xiang-Qing Yu、Eric Buxton、Shiv Patel、Nghi Nguyen、Jon Swaffield、David R. Powell、Alan Wilson、Qingyun Liu

  DOI：10.1021/jm800338j

  日期：2008.7

  The discovery of a novel class of peripheral tryptophan hydroxylase (TPH) inhibitors is described. This class of TPH inhibitors exhibits excellent potency in in vitro biochemical and cell-based assays, and it selectively reduces serotonin levels in the murine intestine after oral administration without affecting levels in the brain. These TPH1 inhibitors may provide novel treatments for gastrointestinal disorders associated with dysregulation of the serotonergic system, such as chemotherapy-induced emesis and irritable bowel syndrome.