N-[2-({2-[(2-aminoethyl)amino]ethyl}amino)ethyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide | 1263357-36-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-[2-({2-[(2-aminoethyl)amino]ethyl}amino)ethyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide
• 英文别名: N-[2-[2-(2-aminoethylamino)ethylamino]ethyl]-4-hydroxy-1-methyl-2-oxoquinoline-3-carboxamide
• CAS: 1263357-36-3
• 化学式: C₁₇H₂₅N₅O₃
• 分子量: 347.417
• InChiKey: KVYYZNYNSCMRTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  120
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,2-二氢-4-羟基-1-甲基-2-氧代-3-喹啉羧酸乙酯 、 三乙烯四胺 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 2.0h， 以10%的产率得到N-[2-({2-[(2-aminoethyl)amino]ethyl}amino)ethyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide
  参考文献：
  名称：

  Synthesis, biological assessment and molecular modeling of new dihydroquinoline-3-carboxamides and dihydroquinoline-3-carbohydrazide derivatives as cholinesterase inhibitors, and Ca channel antagonists

  摘要：

  The synthesis, biological evaluation, and molecular modeling of new 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamides(4), 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carbohydrazide (6), and some hexahydropyrimido[5,4-c]quinoline-2,5-diones (9) produced earlier by our laboratory, as AChE/BuChE inhibitors, is described. From these analyses compound 4c resulted equipotent regarding the inhibition of cholinesterases'; inhibitors 6k, 9a, 9b were selective for AChE, whereas product 4d proved selective for BuChE. Docking analysis has been carry out in order to identify the binding mode in the active site, and to explain the observed selectivities. Only compound 9a has been shown to decrease K+-induced calcium signals in bovine chromaffin cells. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.08.054

文献信息

• Synthesis, biological assessment and molecular modeling of new dihydroquinoline-3-carboxamides and dihydroquinoline-3-carbohydrazide derivatives as cholinesterase inhibitors, and Ca channel antagonists
  作者：Isabelle Tomassoli、Lhassane Ismaili、Marc Pudlo、Cristóbal de los Ríos、Elena Soriano、Inés Colmena、Luis Gandía、Luis Rivas、Abdelouahid Samadi、José Marco-Contelles、Bernard Refouvelet

  DOI：10.1016/j.ejmech.2010.08.054

  日期：2011.1

  The synthesis, biological evaluation, and molecular modeling of new 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamides(4), 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carbohydrazide (6), and some hexahydropyrimido[5,4-c]quinoline-2,5-diones (9) produced earlier by our laboratory, as AChE/BuChE inhibitors, is described. From these analyses compound 4c resulted equipotent regarding the inhibition of cholinesterases'; inhibitors 6k, 9a, 9b were selective for AChE, whereas product 4d proved selective for BuChE. Docking analysis has been carry out in order to identify the binding mode in the active site, and to explain the observed selectivities. Only compound 9a has been shown to decrease K+-induced calcium signals in bovine chromaffin cells. (C) 2010 Elsevier Masson SAS. All rights reserved.