(2S)-2-amino-3-(4-(2-amino-6-(2,2,2-trifluoro-1-(naphthalen-2-yl)ethoxy)pyrimidin-4-yl)phenyl)propanoic acid | 1040530-74-2

• 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: (2S)-2-amino-3-(4-(2-amino-6-(2,2,2-trifluoro-1-(naphthalen-2-yl)ethoxy)pyrimidin-4-yl)phenyl)propanoic acid
• 英文别名: (2S)-2-amino-3-[4-[2-amino-6-(2,2,2-trifluoro-1-naphthalen-2-ylethoxy)pyrimidin-4-yl]phenyl]propanoic acid
• CAS: 1040530-74-2
• 化学式: C₂₅H₂₁F₃N₄O₃
• 分子量: 482.462
• InChiKey: UWSJNTAQMVFLHD-YDNXMHBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  4-chloro-6-(2,2,2-trifluoro-1-(naphthalen-2-yl)ethoxy)pyrimidin-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 (2S)-2-amino-3-(4-(2-amino-6-(2,2,2-trifluoro-1-(naphthalen-2-yl)ethoxy)pyrimidin-4-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

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.