[2-Amino-6-(4-chloro-benzylamino)-pyridin-3-yl]-carbamic acid ethyl ester; hydrochloride

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [2-Amino-6-(4-chloro-benzylamino)-pyridin-3-yl]-carbamic acid ethyl ester; hydrochloride
• 英文别名: ethyl N-[2-amino-6-[(4-chlorophenyl)methylamino]pyridin-1-ium-3-yl]carbamate;chloride
• 化学式: C₁₅H₁₇ClN₄O₂*ClH
• 分子量: 357.24
• InChiKey: IRJRRRVZWGWLOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  89.3
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,6-二氯-3-硝基吡啶 在 镍 氨 、 氢气 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 50.0 ℃ 、500.0 kPa 条件下， 反应 1.0h， 生成 [2-Amino-6-(4-chloro-benzylamino)-pyridin-3-yl]-carbamic acid ethyl ester; hydrochloride
  参考文献：
  名称：

  Synthesis and Quantitative Structure-Activity Relationships of Anticonvulsant 2,3,6-Triaminopyridines

  摘要：

  The synthesis of 2,3,6-triaminopyridine derivatives, representing a unique chemical structure for anticonvulsants, is described. The synthetic program was performed (a) to identify more potent analogs, (b) to determine structural properties controlling potency as well as neurotoxicity, and (c) to reduce the requirements for animal testing. As a result, besides other structural properties, the overall molecular Lipophilicity (log k', octanol-coated column) explained changes in anticonvulsant potency and neurotoxicity. Mimicking the interaction of the amphiphilic triaminopyridines with biological membranes, NMR experiments in the presence of lecithin vesicles were conducted in order to measure the phospholipid-binding parameter log h(1/T-2). Replacement of log k' with log Delta(1/T-2) in the correlation analysis afforded a more significant equation describing the anticonvulsant activity of 21 derivatives.

  DOI：

  10.1021/jm00045a005

文献信息

• 2-Amino-3-Acylamino-6-benzylamino-pyridin-Derivate mit anti-epileptischer Wirkung
  申请人：Degussa Aktiengesellschaft

  公开号：EP0110091A1

  公开（公告）日：1984-06-13

  Verbindungen der Formel worin R eine C1-C4-Alkylgruppe, eine C1-C4-Alkoxygruppe, eine Phenoxygruppe oder eine Phenyl-C1-C2-alkoxygruppe, R, Wasserstoff oder eine C1-C4-Alkylgruppe und R5 Wasserstoff oder eine C1-C4-Alkylgruppe bedeutet und die Reste R2, R3 und R4 gleich oder verschieden sind und Wasserstoff, Halogenatome, Cl-C4-Alkylgruppen, C1-C4-Alkylcarbonylgruppen, die Aminosulfonylgruppe, die Trifluormethylgruppe oder eine C1-C4-Alkylcarbonylaminogruppe bedeuten und deren Säureadditionssalze sind antiepileptisch wirksam.

  式中的化合物 其中 R 是 C1-C4- 烷基、C1-C4-烷氧基、苯氧基或苯基-C1-C2-烷氧基，R 是氢或 C1-C4- 烷基，R5 是氢或 C1-C4- 烷基，基 R2、R3 和 R4 相同或不同，表示氢、卤素原子、Cl-C4-烷基、C1-C4-烷基羰基、氨基磺酰基、R3和R4相同或不同，表示氢、卤素原子、Cl-C4-烷基、C1-C4-烷基羰基、氨基磺酰基、三氟甲基或C1-C4-烷基羰基氨基，其酸加成盐具有抗癫痫活性。
• US4554281A
  申请人：——

  公开号：US4554281A

  公开（公告）日：1985-11-19
• Synthesis and Quantitative Structure-Activity Relationships of Anticonvulsant 2,3,6-Triaminopyridines
  作者：Joachim K. Seydel、Klaus-J. Schaper、Eugene A. Coats、Hans P. Cordes、Peter Emig、Juergen Engel、Bernhard Kutscher、Emmanuel E. Polymeropoulos

  DOI：10.1021/jm00045a005

  日期：1994.9

  The synthesis of 2,3,6-triaminopyridine derivatives, representing a unique chemical structure for anticonvulsants, is described. The synthetic program was performed (a) to identify more potent analogs, (b) to determine structural properties controlling potency as well as neurotoxicity, and (c) to reduce the requirements for animal testing. As a result, besides other structural properties, the overall molecular Lipophilicity (log k', octanol-coated column) explained changes in anticonvulsant potency and neurotoxicity. Mimicking the interaction of the amphiphilic triaminopyridines with biological membranes, NMR experiments in the presence of lecithin vesicles were conducted in order to measure the phospholipid-binding parameter log h(1/T-2). Replacement of log k' with log Delta(1/T-2) in the correlation analysis afforded a more significant equation describing the anticonvulsant activity of 21 derivatives.