3-[3-(benzyl(methyl)amino)propyl]-1H-quinazoline-2,4-dione | 1213701-04-2

• 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: 3-[3-(benzyl(methyl)amino)propyl]-1H-quinazoline-2,4-dione
• 英文别名: 3-[3-[benzyl(methyl)amino]propyl]-1H-quinazoline-2,4-dione
• CAS: 1213701-04-2
• 化学式: C₁₉H₂₁N₃O₂
• 分子量: 323.395
• InChiKey: GEBVMDZXTUAGBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  52.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氨基-N-[3-(苄基(甲基)氨基)丙基]苯甲酰胺 、 N,N'-羰基二咪唑 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以99%的产率得到3-[3-(benzyl(methyl)amino)propyl]-1H-quinazoline-2,4-dione
  参考文献：
  名称：

  Sigma-1 ligands: Tic-hydantoin as a key pharmacophore

  摘要：

  Sigma-1 receptors are involved in numerous pathological dysfunctions and the synthesis of selective ligands is of interest. We identified a fused tetrahydroisoquinoline-hydantoin (Tic-hydantoin) structure with high affinity and selectivity for these receptors. We report here our efforts towards the pharma-comodulation of this substructure, the synthesis of 9 analogs with stereochemistry inversion, opening of isoquinoline ring, removal of isoquinoline nitrogen, replacement of isoquinoline by pyridine, of Tic-hydantoin moiety by quinazolinedione heterocycle. All these analogs provided a loss in the affinity for the sigma-1 receptor. The present work underlines the real importance of the Tic-hydantoin moiety for the obtainment of high affinity ligands. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.10.004

文献信息

• Sigma-1 ligands: Tic-hydantoin as a key pharmacophore
  作者：Marion Toussaint、Deborah Mousset、Catherine Foulon、Ulrich Jacquemard、Claude Vaccher、Patricia Melnyk

  DOI：10.1016/j.ejmech.2009.10.004

  日期：2010.1

  Sigma-1 receptors are involved in numerous pathological dysfunctions and the synthesis of selective ligands is of interest. We identified a fused tetrahydroisoquinoline-hydantoin (Tic-hydantoin) structure with high affinity and selectivity for these receptors. We report here our efforts towards the pharma-comodulation of this substructure, the synthesis of 9 analogs with stereochemistry inversion, opening of isoquinoline ring, removal of isoquinoline nitrogen, replacement of isoquinoline by pyridine, of Tic-hydantoin moiety by quinazolinedione heterocycle. All these analogs provided a loss in the affinity for the sigma-1 receptor. The present work underlines the real importance of the Tic-hydantoin moiety for the obtainment of high affinity ligands. (C) 2009 Elsevier Masson SAS. All rights reserved.