4-(4-Methoxy-pyridin-2-ylamino)-piperidine-1-carboxylic acid ethyl ester | 268730-55-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-(4-Methoxy-pyridin-2-ylamino)-piperidine-1-carboxylic acid ethyl ester
• 英文别名: Ethyl 4-[(4-methoxypyridin-2-yl)amino]piperidine-1-carboxylate
• CAS: 268730-55-8
• 化学式: C₁₄H₂₁N₃O₃
• 分子量: 279.339
• InChiKey: GCTVYNAQYNTXBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  63.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(4-Methoxy-pyridin-2-ylamino)-piperidine-1-carboxylic acid ethyl ester 在 氢氧化钾 、 N,N'-羰基二咪唑 作用下， 以 乙二醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.83h， 生成 (4-Chloro-phenyl)-[4-(4-methoxy-pyridin-2-ylamino)-piperidin-1-yl]-methanone
  参考文献：
  名称：

  2-Aminopyridines as Highly Selective Inducible Nitric Oxide Synthase Inhibitors. Differential Binding Modes Dependent on Nitrogen Substitution

  摘要：

  4-Methylaminopyridine (4-MAP) (5) is a potent but nonselective nitric oxide synthase (NOS) inhibitor. While simple N-methylation in this series results in poor activity, more elaborate N-substitution such as with 4-piperidine carbamate or amide results in potent and selective inducible NOS inhibition. Evidently, a flipping of the pyridine ring between these new inhibitors allows the piperidine to interact with different residues and confer excellent selectivity.

  DOI：

  10.1021/jm031035n
• 作为产物：
  描述：

  4-氨基-1-哌啶甲酸乙酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium tert-butylate 、 palladium diacetate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 4-(4-Methoxy-pyridin-2-ylamino)-piperidine-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  2-Aminopyridines as Highly Selective Inducible Nitric Oxide Synthase Inhibitors. Differential Binding Modes Dependent on Nitrogen Substitution

  摘要：

  4-Methylaminopyridine (4-MAP) (5) is a potent but nonselective nitric oxide synthase (NOS) inhibitor. While simple N-methylation in this series results in poor activity, more elaborate N-substitution such as with 4-piperidine carbamate or amide results in potent and selective inducible NOS inhibition. Evidently, a flipping of the pyridine ring between these new inhibitors allows the piperidine to interact with different residues and confer excellent selectivity.

  DOI：

  10.1021/jm031035n

文献信息

• [EN] COMPOUNDS<br/>[FR] COMPOSES
  申请人：ASTRAZENECA UK LTD

  公开号：WO2000027842A1

  公开（公告）日：2000-05-18

  There are provided novel compounds of formula (I) wherein R?1, R2, R3, R4, R5¿, A, Q, X, Y, and Z are as defined in the specification, and pharmaceutically acceptable salts thereof, and enantiomers and tautomers thereof; together with processes for their preparation, compositions containing them and their use in therapy. The compounds are inhibitors of the enzyme nitric oxide synthase and are thereby particularly useful in the treatment or prophylaxis of inflammatory disease and pain.

  提供了式（I）的新化合物，其中R?1，R2，R3，R4，R5¿，A，Q，X，Y和Z如规范所定义，以及其药学上可接受的盐，对映异构体和互变异构体；以及它们的制备方法，含有它们的组合物以及它们在治疗中的用途。这些化合物是一氧化氮合酶的抑制剂，因此在治疗或预防炎症性疾病和疼痛方面特别有用。
• COMPOUNDS
  申请人：AstraZeneca AB

  公开号：EP1124821A1

  公开（公告）日：2001-08-22
• 2-Aminopyridines as Highly Selective Inducible Nitric Oxide Synthase Inhibitors. Differential Binding Modes Dependent on Nitrogen Substitution
  作者：Stephen Connolly、Anders Aberg、Andrew Arvai、Haydn G. Beaton、David R. Cheshire、Anthony R. Cook、Sally Cooper、David Cox、Peter Hamley、Phil Mallinder、Ian Millichip、David J. Nicholls、Robin J. Rosenfeld、Stephen A. St-Gallay、John Tainer、Alan C. Tinker、Alan V. Wallace

  DOI：10.1021/jm031035n

  日期：2004.6.1

  4-Methylaminopyridine (4-MAP) (5) is a potent but nonselective nitric oxide synthase (NOS) inhibitor. While simple N-methylation in this series results in poor activity, more elaborate N-substitution such as with 4-piperidine carbamate or amide results in potent and selective inducible NOS inhibition. Evidently, a flipping of the pyridine ring between these new inhibitors allows the piperidine to interact with different residues and confer excellent selectivity.