ethyl 3-amino-3-(4-phenylpiperazino)propenoate | 79823-34-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: ethyl 3-amino-3-(4-phenylpiperazino)propenoate
• 英文别名: 3-Amino-3-(4-phenyl-1-piperazinyl)acrylsaeure-ethylester；Ethyl 3-amino-3-(4-phenylpiperazin-1-yl)prop-2-enoate
• CAS: 79823-34-0
• 化学式: C₁₅H₂₁N₃O₂
• 分子量: 275.351
• InChiKey: XQRVALIJVMQPHT-UHFFFAOYSA-N

物化性质

• 熔点：
  125-127°C
• 沸点：
  457.3±45.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  58.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-amino-3-(4-phenylpiperazino)propenoate 在 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.33h， 生成 5-Methoxy-1-methyl-2-(4-phenyl-piperazin-1-yl)-1H-indole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Design and Synthesis of Novel 2-Amino-5-hydroxyindole Derivatives That Inhibit Human 5-Lipoxygenase

  摘要：

  Compounds that inhibit 5-lipoxygenase (5-LO), the key enzyme in the biosynthesis of leukotrienes (LTs), possess potential for the treatment of inflammatory and allergic diseases as well as of atherosclerosis and cancer. Here we present the design and the synthesis of a series of novel 2-amino-5-hydroxyindoles that potently inhibit isolated human recombinant 5-LO as well as 5-LO in polymorphonuclear leukocytes, exemplified by ethyl 2-[(3-chlorophenyl)amino]-5-hydroxy-1H-indole-3-carboxylate (3n, IC50 value congruent to 300 nM). Introduction of an aryl/arylethylamino group or 4-arylpiperazin-1-yl residues into position 2 of the 5-hydroxyindoles was essential for biological activity. Whereas the 4-arylpiperazin-1-yl derivatives were more potent in cell-free assays as compared to intact cell test systems, aryl/arylethylamino derivatives inhibited 5-LO activity in intact cells and cell-free assays almost equally well. On the basis of their 5-LO inhibitory properties, these novel 2-amino-5-hydroxyindoles represent potential candidates for the pharmacological intervention with LT-associated diseases.

  DOI：

  10.1021/jm050801i
• 作为产物：
  描述：

  N-苯基哌嗪 、 2-丙烯酸,3-氨基-3-乙氧基-,乙基酯,(2E)- 以 乙醇 为溶剂， 反应 48.0h， 生成 ethyl 3-amino-3-(4-phenylpiperazino)propenoate
  参考文献：
  名称：

  Design and Synthesis of Novel 2-Amino-5-hydroxyindole Derivatives That Inhibit Human 5-Lipoxygenase

  摘要：

  Compounds that inhibit 5-lipoxygenase (5-LO), the key enzyme in the biosynthesis of leukotrienes (LTs), possess potential for the treatment of inflammatory and allergic diseases as well as of atherosclerosis and cancer. Here we present the design and the synthesis of a series of novel 2-amino-5-hydroxyindoles that potently inhibit isolated human recombinant 5-LO as well as 5-LO in polymorphonuclear leukocytes, exemplified by ethyl 2-[(3-chlorophenyl)amino]-5-hydroxy-1H-indole-3-carboxylate (3n, IC50 value congruent to 300 nM). Introduction of an aryl/arylethylamino group or 4-arylpiperazin-1-yl residues into position 2 of the 5-hydroxyindoles was essential for biological activity. Whereas the 4-arylpiperazin-1-yl derivatives were more potent in cell-free assays as compared to intact cell test systems, aryl/arylethylamino derivatives inhibited 5-LO activity in intact cells and cell-free assays almost equally well. On the basis of their 5-LO inhibitory properties, these novel 2-amino-5-hydroxyindoles represent potential candidates for the pharmacological intervention with LT-associated diseases.

  DOI：

  10.1021/jm050801i

文献信息

• Meyer, Horst, Liebigs Annalen der Chemie, 1981, # 9, p. 1534 - 1544
  作者：Meyer, Horst

  DOI：——

  日期：——
• Cocco, Maria Teresa; Congiu, Cenzo; Onnis, Valentina, Journal of Heterocyclic Chemistry, 1995, vol. 32, # 2, p. 463 - 466
  作者：Cocco, Maria Teresa、Congiu, Cenzo、Onnis, Valentina

  DOI：——

  日期：——
• Design and Synthesis of Novel 2-Amino-5-hydroxyindole Derivatives That Inhibit Human 5-Lipoxygenase
  作者：Jens Landwehr、Sven George、Eva-Maria Karg、Daniel Poeckel、Dieter Steinhilber、Reinhard Troschuetz、Oliver Werz

  DOI：10.1021/jm050801i

  日期：2006.7.1

  Compounds that inhibit 5-lipoxygenase (5-LO), the key enzyme in the biosynthesis of leukotrienes (LTs), possess potential for the treatment of inflammatory and allergic diseases as well as of atherosclerosis and cancer. Here we present the design and the synthesis of a series of novel 2-amino-5-hydroxyindoles that potently inhibit isolated human recombinant 5-LO as well as 5-LO in polymorphonuclear leukocytes, exemplified by ethyl 2-[(3-chlorophenyl)amino]-5-hydroxy-1H-indole-3-carboxylate (3n, IC50 value congruent to 300 nM). Introduction of an aryl/arylethylamino group or 4-arylpiperazin-1-yl residues into position 2 of the 5-hydroxyindoles was essential for biological activity. Whereas the 4-arylpiperazin-1-yl derivatives were more potent in cell-free assays as compared to intact cell test systems, aryl/arylethylamino derivatives inhibited 5-LO activity in intact cells and cell-free assays almost equally well. On the basis of their 5-LO inhibitory properties, these novel 2-amino-5-hydroxyindoles represent potential candidates for the pharmacological intervention with LT-associated diseases.