1-(3,4,5-Trimethoxyphenyl)-1,2-dihydroimidazo[5,1-b]quinazoline-3,9-dione | 1415355-66-6

• 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: 1-(3,4,5-Trimethoxyphenyl)-1,2-dihydroimidazo[5,1-b]quinazoline-3,9-dione
• 英文别名: 1-(3,4,5-trimethoxyphenyl)-1,2-dihydroimidazo[5,1-b]quinazoline-3,9-dione
• CAS: 1415355-66-6
• 化学式: C₁₉H₁₇N₃O₅
• 分子量: 367.361
• InChiKey: ZWSMCBOZAZKEMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  89.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-喹唑啉酮-2-甲酸乙酯 在 ammonium hydroxide 作用下， 反应 5.0h， 生成 1-(3,4,5-Trimethoxyphenyl)-1,2-dihydroimidazo[5,1-b]quinazoline-3,9-dione
  参考文献：
  名称：

  Synthesis and configurational assignment of 1,2-dihydroimidazo[5,1-b]quinazoline-3,9-diones: novel NMDA receptor antagonists

  摘要：

  NMDA receptors form a major subdivision of the ionotropic glutamate receptor family that mediates excitatory synaptic transmission in the brain. Series of 1-substituted 1,2-dihydroimidazo[5,1-b]quinazolinediones were synthesized and found to have potent nanomolar activity at the glycine site of the NMDA receptor. Imidazoquinazolinediones were prepared by cyclocondensation of 4-oxo-quinazoline-2-carboxamide with aldehydes and orthoesters with good yields. The formed enantiomers were separated by chiral HPLC. The absolute configuration of pure enantiomers is elucidated by combined CD/Quantumchemical time-dependent DFT calculation method (TDDFT). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.086