(2R,3R,4S)-2-[({(1R)-1-[4-(benzyloxy)phenyl]-2-hydroxyethyl}amino)methyl]pyrrolidine-3,4-diol | 1159576-42-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R,3R,4S)-2-[({(1R)-1-[4-(benzyloxy)phenyl]-2-hydroxyethyl}amino)methyl]pyrrolidine-3,4-diol
• 英文别名: (2R,3R,4S)-2{{(1R)-2-hydroxy-1-{4-[(phenylmethoxy)phenyl]hydroxyethyl}amino}methyl}pyrrolidine-3,4-diol；(2R,3R,4S)-2-[[[(1R)-2-hydroxy-1-(4-phenylmethoxyphenyl)ethyl]amino]methyl]pyrrolidine-3,4-diol
• CAS: 1159576-42-7
• 化学式: C₂₀H₂₆N₂O₄
• 分子量: 358.437
• InChiKey: CWHWIEJOOOHEJA-FUMNGEBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  94
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  tert-butyl (3aR,4R,6aS)-2,2-dimethyl-4-{{{(1R)-2-hydroxy-1-[4-(phenylmethoxy)phenyl]ethyl}amino}methyl}-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 3.0h， 以42%的产率得到(2R,3R,4S)-2-[({(1R)-1-[4-(benzyloxy)phenyl]-2-hydroxyethyl}amino)methyl]pyrrolidine-3,4-diol
  参考文献：
  名称：

  Novel 2-[(benzylamino)methyl]pyrrolidine-3,4-diol derivatives as α-mannosidase inhibitors and with antitumor activities against hematological and solid malignancies

  摘要：

  Novel alpha-mannosidase inhibitors of the type (2R,3R,4S)-2-({[(1R)-2- hydroxy-1-arylethyl]amine}methyl) pyrrolidine-3,4-diol have been prepared and assayed for their anticancer activities. Compound 30 with the aryl group = 4-trifluoromethylbiphenyl inhibits the proliferation of primary cells and cell lines of different origins, irrespective of Bcl-2 expression levels, inducing a G2/Mcell cycle arrest and by modification of genes involved in cell cycle progression and survival. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.009

文献信息

• Novel 2-[(benzylamino)methyl]pyrrolidine-3,4-diol derivatives as α-mannosidase inhibitors and with antitumor activities against hematological and solid malignancies
  作者：Claudia Bello、Michele Cea、Giovanna Dal Bello、Anna Garuti、Ilaria Rocco、Gabriella Cirmena、Eva Moran、Aimable Nahimana、Michel A. Duchosal、Floriana Fruscione、Paolo Pronzato、Francesco Grossi、Franco Patrone、Alberto Ballestrero、Marc Dupuis、Bernard Sordat、Alessio Nencioni、Pierre Vogel

  DOI：10.1016/j.bmc.2010.03.009

  日期：2010.5

  Novel alpha-mannosidase inhibitors of the type (2R,3R,4S)-2-([(1R)-2- hydroxy-1-arylethyl]amine}methyl) pyrrolidine-3,4-diol have been prepared and assayed for their anticancer activities. Compound 30 with the aryl group = 4-trifluoromethylbiphenyl inhibits the proliferation of primary cells and cell lines of different origins, irrespective of Bcl-2 expression levels, inducing a G2/Mcell cycle arrest and by modification of genes involved in cell cycle progression and survival. (C) 2010 Elsevier Ltd. All rights reserved.