6-amino-5-cyano-4-(4-fluorophenyl)-2-methyl-3-pyridinecarboxylic acid ethyl ester | 702698-97-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-amino-5-cyano-4-(4-fluorophenyl)-2-methyl-3-pyridinecarboxylic acid ethyl ester
• 英文别名: ethyl 6-amino-5-cyano-2-methyl-4-(4-fluorophenyl)nicotinate
• CAS: 702698-97-3
• 化学式: C₁₆H₁₄FN₃O₂
• 分子量: 299.304
• InChiKey: SMXYGODPRUKULW-UHFFFAOYSA-N

物化性质

• 熔点：
  239-241 °C
• 沸点：
  492.4±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  89.0
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  环庚酮 、 6-amino-5-cyano-4-(4-fluorophenyl)-2-methyl-3-pyridinecarboxylic acid ethyl ester 在 三氯化铝 作用下， 以 1,2-二氯乙烷 为溶剂， 以70%的产率得到5-Amino-4-(4-fluoro-phenyl)-2-methyl-7,8,9,10-tetrahydro-6H-cyclohepta[b][1,8]naphthyridine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular modelling of diversely functionalized heterocyclic derivatives as inhibitors of acetylcholinesterase/butyrylcholinesterase and modulators of Ca2+ channels and nicotinic receptors

  摘要：

  The synthesis and the biological activity of compounds 5-40 as inhibitors of acetyleholinesterase (AChE) and butyrylcholinesterase (BuChE), as well as modulators of voltage-dependent Ca2+ channels and nicotinic receptors, are described. These molecules are tacrine analogues, which have been prepared from polyfunctionalized 6-amino-5-cyano-4H-pyrans, 6-amino-5-cyano-pyridines and 5-amino-2-aryl-3-cyano-1,3-oxazoles via Friedlander reaction with selected cycloalkanones. These compounds are moderate acetylcholinesterase and butyrylcholinesterase inhibitors, the BuChE/AChE selectivity of the most active molecules ranges from 10.0 (compound 29) to 76.9 (compound 16). Interestingly, the 'oxazolo-tacrine' derivatives are devoid of any activity. All compounds showed an important inhibitory effect on the nicotinic acetylcholine receptor. Most of them also blocked L-type Ca2+ channels, and three of them, 64, 19 and 67, the non-L type of Ca2+ channels. Molecular modelling studies suggest that these compounds might bind at the peripheral binding site of AChE, which opens the possibility to design inhibitors able to bind at both, the catalytic and peripheral binding sites of the enzyme. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.02.017
• 作为产物：
  描述：

  2-(4-氟亚苄基)-丙二腈 在 哌啶 、 乙酸铵 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 6-amino-5-cyano-4-(4-fluorophenyl)-2-methyl-3-pyridinecarboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular modelling of diversely functionalized heterocyclic derivatives as inhibitors of acetylcholinesterase/butyrylcholinesterase and modulators of Ca2+ channels and nicotinic receptors

  摘要：

  The synthesis and the biological activity of compounds 5-40 as inhibitors of acetyleholinesterase (AChE) and butyrylcholinesterase (BuChE), as well as modulators of voltage-dependent Ca2+ channels and nicotinic receptors, are described. These molecules are tacrine analogues, which have been prepared from polyfunctionalized 6-amino-5-cyano-4H-pyrans, 6-amino-5-cyano-pyridines and 5-amino-2-aryl-3-cyano-1,3-oxazoles via Friedlander reaction with selected cycloalkanones. These compounds are moderate acetylcholinesterase and butyrylcholinesterase inhibitors, the BuChE/AChE selectivity of the most active molecules ranges from 10.0 (compound 29) to 76.9 (compound 16). Interestingly, the 'oxazolo-tacrine' derivatives are devoid of any activity. All compounds showed an important inhibitory effect on the nicotinic acetylcholine receptor. Most of them also blocked L-type Ca2+ channels, and three of them, 64, 19 and 67, the non-L type of Ca2+ channels. Molecular modelling studies suggest that these compounds might bind at the peripheral binding site of AChE, which opens the possibility to design inhibitors able to bind at both, the catalytic and peripheral binding sites of the enzyme. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.02.017

文献信息

• The Sandmeyer Reaction on Some Selected Heterocyclic Ring Systems: Synthesis of Useful 2-Chloroheterocyclic-3-carbonitrile Intermediates
  作者：Abdelouahid Samadi、José Marco-Contelles、Daniel da Silva、Mourad Chioua、Maria do Carmo Carreiras

  DOI：10.1055/s-0030-1258149

  日期：2010.8

  The Sandmeyer reaction on some selected heterocycles bearing the 2-amino-3-carbonitrile structural moiety has been investigated in order to prepare the corresponding 2-chloro-3-carbo­nitrile derivatives as synthetic useful intermediates for further development. Sandmeyer reaction - 2-amino(heterocyclic)-3-carbo­nitriles - 2-aminopyrazoles - 2-aminooxazoles - 2-amino-4H-pyrans - 2-amino-1,4-dihydropyridines

  为了制备相应的2-氯-3-腈衍生物作为合成有用的中间体用于进一步开发，已经研究了在一些带有2-氨基-3-腈结构部分的选定杂环上的Sandmeyer反应。 桑德梅尔反应-2-氨基（杂环）-3-腈-2-氨基吡唑-2-氨基恶唑-2-氨基-4 H-吡喃-2-氨基-1,4-二氢吡啶-2-氨基吡啶-2-氯（杂环） ）-3-腈