{1-[3-(benzyl(methyl)amino)propylcarbamoyl]-2-phenylethyl}methylcarbamic acid tert-butyl ester | 1213700-98-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: {1-[3-(benzyl(methyl)amino)propylcarbamoyl]-2-phenylethyl}methylcarbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(2S)-1-[3-[benzyl(methyl)amino]propylamino]-1-oxo-3-phenylpropan-2-yl]-N-methylcarbamate
• CAS: 1213700-98-1
• 化学式: C₂₆H₃₇N₃O₃
• 分子量: 439.598
• InChiKey: QNBAJRUWKJWKGF-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  61.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  {1-[3-(benzyl(methyl)amino)propylcarbamoyl]-2-phenylethyl}methylcarbamic acid tert-butyl ester 在 三氟乙酸 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 0.75h， 生成
  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：

  Boc-N-甲基-L-苯丙氨酸 、 N-(3-氨基丙基)-n-苄基-n-甲胺 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以50 mg的产率得到{1-[3-(benzyl(methyl)amino)propylcarbamoyl]-2-phenylethyl}methylcarbamic acid tert-butyl ester
  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.