(Z)-3-[3-(benzyl(methyl)amino)propylcarbamoyl]acrylic acid | 1213700-93-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-3-[3-(benzyl(methyl)amino)propylcarbamoyl]acrylic acid
• 英文别名: (Z)-4-[3-[benzyl(methyl)amino]propylamino]-4-oxobut-2-enoic acid
• CAS: 1213700-93-6
• 化学式: C₁₅H₂₀N₂O₃
• 分子量: 276.335
• InChiKey: MVZNPEOCYHNUFQ-HJWRWDBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-3-[3-(benzyl(methyl)amino)propylcarbamoyl]acrylic acid 在 乙酸酐 、 溶剂黄146 作用下， 反应 24.0h， 以82 mg的产率得到1-[3-(benzyl(methyl)amino)propyl]pyrrole-2,5-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
• 作为产物：
  描述：

  马来酸酐 、 N-(3-氨基丙基)-n-苄基-n-甲胺 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以228 mg的产率得到(Z)-3-[3-(benzyl(methyl)amino)propylcarbamoyl]acrylic acid
  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.