5-bromo-N-((9-ethyl-9H-carbazol-3-yl)methyl)pyrazin-2-amine | 1040527-65-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-bromo-N-((9-ethyl-9H-carbazol-3-yl)methyl)pyrazin-2-amine
• 英文别名: (5-bromo-pyrazine-2-yl)-(9-ethyl-9H-carbazol-3-ylmethyl)amine；5-bromo-N-[(9-ethylcarbazol-3-yl)methyl]pyrazin-2-amine
• CAS: 1040527-65-8
• 化学式: C₁₉H₁₇BrN₄
• 分子量: 381.275
• InChiKey: HGJFVIJQODQUHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  42.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-N-((9-ethyl-9H-carbazol-3-yl)methyl)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-((9-ethyl-9H-carbazol-3-yl)methylamino)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 、 N-乙基咔唑-3-甲醛 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以1.06 g的产率得到5-bromo-N-((9-ethyl-9H-carbazol-3-yl)methyl)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

• [EN] TRYPTOPHAN HYDROXYLASE INHIBITORS AND METHODS OF THEIR USE<br/>[FR] INHIBITEURS DE LA TRYPTOPHANE HYDROXYLASE ET PROCÉDÉS D'UTILISATION ASSOCIÉS
  申请人：LEXICON PHARMACEUTICALS INC

  公开号：WO2010039957A1

  公开（公告）日：2010-04-08

  Compounds, compositions and methods of treating serotonin-mediated diseases and disorders are disclosed.

  揭示了治疗与血清素介导的疾病和紊乱的化合物、组合物和方法。