N-(4-(8,9,10,11-tetrahydro-6H-azocino[2,1-b]quinazolin-13(7H)-ylideneamino)butyl)-N-(3-(8,9,10,11-tetrahydro-6H-azocino[2,1-b]quinazolin-13(7H)-ylideneamino)propyl)methacrylamide | 1276655-68-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N-(4-(8,9,10,11-tetrahydro-6H-azocino[2,1-b]quinazolin-13(7H)-ylideneamino)butyl)-N-(3-(8,9,10,11-tetrahydro-6H-azocino[2,1-b]quinazolin-13(7H)-ylideneamino)propyl)methacrylamide
• 英文别名: N-(4-(8,9,10,11-Tetrahydro-6H-azocino[2,1-b]quinazolin-13(7H)-ylideneamino)butyl)-N-(3-(8,9,10,11-tetrahydro-6H-azocino[2,1-b]quinazolin-13(7H)-ylideneamino)propyl)-methacrylamide；N-[4-(6,7,8,9,10,11-hexahydroazocino[2,1-b]quinazolin-13-ylideneamino)butyl]-N-[3-(6,7,8,9,10,11-hexahydroazocino[2,1-b]quinazolin-13-ylideneamino)propyl]-2-methylprop-2-enamide
• CAS: 1276655-68-5
• 化学式: C₃₉H₅₁N₇O
• 分子量: 633.88
• InChiKey: CSCOWQRMRPBTSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  47
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  azacyclooctano<2,1-b>-4(3H)-quinazolinone 在 劳森试剂 、 盐酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 N-(4-(8,9,10,11-tetrahydro-6H-azocino[2,1-b]quinazolin-13(7H)-ylideneamino)butyl)-N-(3-(8,9,10,11-tetrahydro-6H-azocino[2,1-b]quinazolin-13(7H)-ylideneamino)propyl)methacrylamide
  参考文献：
  名称：

  Probing the mid-gorge of cholinesterases with spacer-modified bivalent quinazolinimines leads to highly potent and selective butyrylcholinesterase inhibitors

  摘要：

  The spacer structure of homobivalent quinazolinimes acting as potent acetyl-(AChE)- and butyrylcholinesterase (BChE) inhibitors was chemically modified introducing tertiary amine and acyl-amide moieties, and the activities at both ChEs were evaluated. Molecular docking was applied to explain the data and probe the capacity of the mid-gorge site of both ChEs. The novel spacer structures considerably alter the biological profile of bivalent quinazolinimines with regard to both inhibitory activity and selectivity. Mutual interaction of binding to the various sites of the enzymes was further investigated by applying also different spacer lengths and ring sizes of the alicycle of the tricyclic quinazolinimines. In order to achieve selectivity toward BChE and to improve inhibitory activities, the spacer structure was optimized and identified a highly potent and selective BChE inhibitor. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.12.034

文献信息

• Probing the mid-gorge of cholinesterases with spacer-modified bivalent quinazolinimines leads to highly potent and selective butyrylcholinesterase inhibitors
  作者：Xinyu Chen、Irina G. Tikhonova、Michael Decker

  DOI：10.1016/j.bmc.2010.12.034

  日期：2011.2

  The spacer structure of homobivalent quinazolinimes acting as potent acetyl-(AChE)- and butyrylcholinesterase (BChE) inhibitors was chemically modified introducing tertiary amine and acyl-amide moieties, and the activities at both ChEs were evaluated. Molecular docking was applied to explain the data and probe the capacity of the mid-gorge site of both ChEs. The novel spacer structures considerably alter the biological profile of bivalent quinazolinimines with regard to both inhibitory activity and selectivity. Mutual interaction of binding to the various sites of the enzymes was further investigated by applying also different spacer lengths and ring sizes of the alicycle of the tricyclic quinazolinimines. In order to achieve selectivity toward BChE and to improve inhibitory activities, the spacer structure was optimized and identified a highly potent and selective BChE inhibitor. (C) 2010 Elsevier Ltd. All rights reserved.