AR-H061719 | 344413-63-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: AR-H061719
• 英文别名: (3-amino-2-fluoropropyl)phosphinic acid；(2R)-(3-amino-2-fluoropropyl)phosphinic acid
• CAS: 344413-63-4
• 化学式: C₃H₉FNO₂P
• 分子量: 141.082
• InChiKey: LJNUIEQATDYXJH-UHFFFAOYSA-N

物化性质

• 沸点：
  306.1±52.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.25
• 重原子数：
  8.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  63.32
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  AR-H061719 、 苯甲酰氯 在 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 18.0h， 以52%的产率得到
  参考文献：
  名称：

  Synthesis and Pharmacological Evaluation of Novel γ-Aminobutyric Acid Type B (GABA_B) Receptor Agonists as Gastroesophageal Reflux Inhibitors

  摘要：

  We have previously demonstrated that the prototypical GABA(B) receptor agonist baclofen inhibits transient lower esophageal sphincter relaxations (TLESRs), the most important mechanism for gastroesophageal reflux. Thus, GABAB agonists could be exploited for the treatment of gastroesophageal reflux disease. However, baclofen, which is used as an antispastic agent, and other previously known GABAB agonists can produce CNS side effects such as sedation, dizziness, nausea, and vomiting at higher doses. We now report the discovery of atypical GABAB agonists devoid of classical GABAB agonist related CNS side effects at therapeutic doses and the optimization of this type of compound for inhibition of TLESRs, which has resulted in a candidate drug (R)-7 (AZD3355) that is presently being evaluated in man.

  DOI：

  10.1021/jm701425k
• 作为产物：
  描述：

  在 盐酸 、 水 作用下， 以 甲醇 、 水 为溶剂， 反应 2.5h， 以645 mg的产率得到AR-H061719
  参考文献：
  名称：

  Synthesis and Pharmacological Evaluation of Novel γ-Aminobutyric Acid Type B (GABA_B) Receptor Agonists as Gastroesophageal Reflux Inhibitors

  摘要：

  We have previously demonstrated that the prototypical GABA(B) receptor agonist baclofen inhibits transient lower esophageal sphincter relaxations (TLESRs), the most important mechanism for gastroesophageal reflux. Thus, GABAB agonists could be exploited for the treatment of gastroesophageal reflux disease. However, baclofen, which is used as an antispastic agent, and other previously known GABAB agonists can produce CNS side effects such as sedation, dizziness, nausea, and vomiting at higher doses. We now report the discovery of atypical GABAB agonists devoid of classical GABAB agonist related CNS side effects at therapeutic doses and the optimization of this type of compound for inhibition of TLESRs, which has resulted in a candidate drug (R)-7 (AZD3355) that is presently being evaluated in man.

  DOI：

  10.1021/jm701425k