N-(2-(苯基氨基)乙基)氨基甲酸乙酯 | 86234-54-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-(2-(苯基氨基)乙基)氨基甲酸乙酯
• 英文名称: ethyl N-<2-(phenylamino)ethyl>carbamate
• 英文别名: O-Aethyl-N-(2-anilino-aethyl)-urethan；Ethyl(2-(phenylamino)ethyl)carbamate；ethyl N-(2-anilinoethyl)carbamate
• CAS: 86234-54-0
• 化学式: C₁₁H₁₆N₂O₂
• 分子量: 208.26
• InChiKey: QMSDKYHJBCMIQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-(苯基氨基)乙基)氨基甲酸乙酯 在 劳森试剂 、 盐酸 、 乙基溴化镁 、 溶剂黄146 、 锌 、 sodium nitrite 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 66.5h， 生成 1-phenyl-2H,4H-tetrahydro-1,2,4-triazin-3-thione
  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：

  N-(2-溴乙基)氨基甲酸乙酯 、 苯胺 在 N,N-二异丙基乙胺 作用下， 以 苯 为溶剂， 反应 24.0h， 以63%的产率得到N-(2-(苯基氨基)乙基)氨基甲酸乙酯
  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

• Synthesis of N,N′-disubstituted ureas from carbamates
  作者：Anwer Basha

  DOI：10.1016/s0040-4039(00)86102-x

  日期：1988.1

  A simple synthesis of N,N′-disubstituted ureas from carbamates is described involving displacement of an alkoxy group by the magnesium salt of an amine generated in situ by treatment with ethylmagnesium bromide.

  描述了由氨基甲酸酯简单合成N，N′-二取代的脲的方法，该方法包括通过用乙基溴化镁处理原位产生的胺的镁盐置换烷氧基。
• Pyridinium derivatives useful as PAF antagonists
  申请人：J. URIACH & CIA. S.A.

  公开号：EP0610943A1

  公开（公告）日：1994-08-17

  The present invention relates to novel pyridinium derivatives of formula I wherein R¹ represents C₁₋₆ alkyl or aryl-C₁-₆ alkyl; R² represents aryl; Z is -O- or -NR³-; T is -O-, -NR⁴- or a single bond; R represents C₁₋₁₈ alkyl, C₁₋₁₈ haloalkyl, aryl, heteroaryl, aryl-C₁₋₆ alkyl or heteroaryl-C₁-₆ alkyl, and in addition, when T represents a single bond, R can also represent a phenyl or phenylmethyl radical substituted in the para or meta position by a 2-quinolylmethoxy group; R³ and R⁴ independently represent hydrogen, C₁₋₄ alkyl, aryl or C₁₋₄ alkylcarbonyl, and in addition, R³ and R⁴ may form a ring together when Z= NR³ and T= NR⁴, or R³ may be bonded to R to form a ring when Z= NR³; and W⁻ is a counter anion. These compounds are PAF antagonists.

  本发明涉及公式I的新型吡啶衍生物，其中R¹代表C₁₋₆烷基或芳基-C₁-₆烷基；R²代表芳基；Z为-O-或-NR³-；T为-O-，-NR⁴-或单键；R代表C₁₋₁₈烷基，C₁₋₁₈卤代烷基，芳基，杂环芳基，芳基-C₁₋₆烷基或杂环芳基-C₁-₆烷基，另外，当T代表单键时，R还可以表示在对位或间位被2-喹啉甲氧基基团取代的苯基或苄基基团；R³和R⁴独立地表示氢，C₁₋₄烷基，芳基或C₁₋₄烷基羰基，另外，当Z= NR³且T= NR⁴时，R³和R⁴也可以一起形成环，或者当Z= NR³时，R³可以与R结合形成环；W⁻是一个对离子。这些化合物是PAF拮抗剂。
• Aminoethylation process
  申请人：The Dow Chemical Company

  公开号：US04381401A1

  公开（公告）日：1983-04-26

  2-Oxazolidinone or N-substituted derivatives thereof are reacted with aromatic amine hydrochlorides at elevated temperatures to produce 1,2-ethanediamines.

  2-噁唑啉或其N-取代衍生物在高温下与芳香胺盐酸盐反应，生成1,2-乙二胺。
• Competitive attack of nucleophiles at ring carbon vs carbonyl. Reactions of aziridinecarbamates
  作者：Alfred Hassner、Albert Kascheres

  DOI：10.1016/s0040-4039(00)89391-0

  日期：1970.1
• BASHA, ANWER, TETRAHEDRON LETT., 29,(1988) N 21, C. 2525-2526
  作者：BASHA, ANWER

  DOI：——

  日期：——