2-amino-3-hydroxy-N-phenyl-propionamide | 122612-13-9

• 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: 2-amino-3-hydroxy-N-phenyl-propionamide
• 英文别名: 2-amino-3-hydroxy-N-phenylpropanamide
• CAS: 122612-13-9
• 化学式: C₉H₁₂N₂O₂
• 分子量: 180.206
• InChiKey: OSNHPPYZWLATBV-UHFFFAOYSA-N

物化性质

• 沸点：
  465.3±35.0 °C(Predicted)
• 密度：
  1.281±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  75.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-amino-3-hydroxy-N-phenyl-propionamide 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 methyl N-(1-anilino-3-hydroxypropan-2-yl)carbamate
  参考文献：
  名称：

  5-Lipoxygenase Inhibitors:  Synthesis and Structure−Activity Relationships of a Series of 1-Aryl-2H,4H-tetrahydro-1,2,4-triazin-3-ones

  摘要：

  Synthetic routes were developed to access a variety of novel 1-aryl-2H,4H-tetrahydro-1,2,4-triazin-3-one analogs which were evaluated as 5-lipoxygenase (5-LO) inhibitors. The parent structure, 1-phenylperhydro-1,2,4-triazin-3-one (4), was found to be a selective inhibitor of 5-LO in broken cell, intact cell, and human blood assays with IC50 values of 5-21 mu M. In a rat anaphylaxis model, 4 blocked leukotriene formation with an ED(50) = 7 mg/kg when administered orally. Compound 4 exhibited selectivity for inhibition of 5-LO with little activity against related enzymes: 12-LO from human platelets, 15-LO from soybean, and cyclooxygenase (COX) from sheep seminal vesicle. In pilot subacute toxicity testing, 4 did not produce methemoglobinemia in rats (400 mg/kg po daily for 9 days) or in dogs (200 mg/kg po daily for 28 days). These results indicated that the triazinone structure provided a 5-LO inhibitor template devoid of the toxicity problems observed in the related phenidone (1) and pyridazinone (3) classes of 5-LO inhibitors. The parent compound 4 is a selective, orally bioavailable 5-LO inhibitor which can serve as a useful reference standard for in vivo pharmacological studies involving leukotriene-mediated phenonmena.

  DOI：

  10.1021/jm960372b
• 作为产物：
  描述：

  DL-丝氨酸甲酯盐酸盐 、 苯胺 在 乙基溴化镁 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 72.0h， 以26%的产率得到2-amino-3-hydroxy-N-phenyl-propionamide
  参考文献：
  名称：

  5-Lipoxygenase Inhibitors:  Synthesis and Structure−Activity Relationships of a Series of 1-Aryl-2H,4H-tetrahydro-1,2,4-triazin-3-ones

  摘要：

  Synthetic routes were developed to access a variety of novel 1-aryl-2H,4H-tetrahydro-1,2,4-triazin-3-one analogs which were evaluated as 5-lipoxygenase (5-LO) inhibitors. The parent structure, 1-phenylperhydro-1,2,4-triazin-3-one (4), was found to be a selective inhibitor of 5-LO in broken cell, intact cell, and human blood assays with IC50 values of 5-21 mu M. In a rat anaphylaxis model, 4 blocked leukotriene formation with an ED(50) = 7 mg/kg when administered orally. Compound 4 exhibited selectivity for inhibition of 5-LO with little activity against related enzymes: 12-LO from human platelets, 15-LO from soybean, and cyclooxygenase (COX) from sheep seminal vesicle. In pilot subacute toxicity testing, 4 did not produce methemoglobinemia in rats (400 mg/kg po daily for 9 days) or in dogs (200 mg/kg po daily for 28 days). These results indicated that the triazinone structure provided a 5-LO inhibitor template devoid of the toxicity problems observed in the related phenidone (1) and pyridazinone (3) classes of 5-LO inhibitors. The parent compound 4 is a selective, orally bioavailable 5-LO inhibitor which can serve as a useful reference standard for in vivo pharmacological studies involving leukotriene-mediated phenonmena.

  DOI：

  10.1021/jm960372b

文献信息

• [EN] GLYCINE B ANTAGONISTS<br/>[FR] ANTAGONISTES DE LA GLYCINE B
  申请人：MERZ PHARMA GMBH & CO KGAA

  公开号：WO2010037533A1

  公开（公告）日：2010-04-08

  The invention relates to quinoline derivatives as well as their pharmaceutically acceptable salts. The invention further relates to a process for the preparation of such compounds. The compounds of the invention are glycine B antagonists and are therefore useful for the control and prevention of various disorders, including neurological disorders.

  该发明涉及喹啉衍生物及其药用盐。该发明还涉及一种制备这种化合物的方法。该发明的化合物是甘氨酸B拮抗剂，因此对于控制和预防各种疾病，包括神经系统疾病，非常有用。
• GLYCINE B ANTAGONIST
  申请人：Henrich Markus

  公开号：US20110190342A1

  公开（公告）日：2011-08-04

  The invention relates to quinoline derivatives as well as their pharmaceutically acceptable salts. The invention further relates to a process for the preparation of such compounds. The compounds of the invention are glycine B antagonists and are therefore useful for the control and prevention of various disorders, including neurological disorders.

  本发明涉及喹啉衍生物及其药学上可接受的盐。本发明还涉及制备这种化合物的过程。本发明的化合物是甘氨酸B拮抗剂，因此对控制和预防各种疾病，包括神经系统疾病，非常有用。
• Glycine B antagonist
  申请人：Merz Pharma GmbH & Co. KGaA

  公开号：US08288549B2

  公开（公告）日：2012-10-16

  The invention relates to quinoline derivatives as well as their pharmaceutically acceptable salts. The invention further relates to a process for the preparation of such compounds. The compounds of the invention are glycine B antagonists and are therefore useful for the control and prevention of various disorders, including neurological disorders.

  本发明涉及喹啉衍生物及其药学上可接受的盐。本发明进一步涉及制备这些化合物的方法。本发明的化合物是甘氨酸B拮抗剂，因此对于控制和预防各种疾病，包括神经系统疾病，具有用途。
• GLYCINE B ANTAGONISTS
  申请人：Merz Pharma GmbH & Co. KGaA

  公开号：EP2350014A1

  公开（公告）日：2011-08-03
• US8288549B2
  申请人：——

  公开号：US8288549B2

  公开（公告）日：2012-10-16