(2R,3R,4S)-2-{{[(1R)-2-hydroxy-1-[4'-(prop-2-enyloxy)phenyl]ethyl]amino}methyl}pyrrolidine-3,4-diol | 1159576-38-1

• 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)-2-hydroxy-1-[4'-(prop-2-enyloxy)phenyl]ethyl]amino}methyl}pyrrolidine-3,4-diol
• 英文别名: (2R,3R,4S)-2-[[[(1R)-2-hydroxy-1-(4-prop-2-enoxyphenyl)ethyl]amino]methyl]pyrrolidine-3,4-diol
• CAS: 1159576-38-1
• 化学式: C₁₆H₂₄N₂O₄
• 分子量: 308.378
• InChiKey: VTILUTLLIVHFFV-FXUDXRNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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-(prop-2-enyloxy)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44%的产率得到(2R,3R,4S)-2-{{[(1R)-2-hydroxy-1-[4'-(prop-2-enyloxy)phenyl]ethyl]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

• Derivatives of Dihydroxypyrrolidine as Anti-Cancer Compounds
  申请人：EPFL Ecole Polytechnique Fédérale de Lausanne

  公开号：EP2067771A1

  公开（公告）日：2009-06-10

  The present invention relates to derivatives of dihydroxypyrrolidine useful in the treatment of cancer. The invention further relates to a process for making the compounds. The compounds are inhibitors of α mannosidase, and possibly, also inhibit nicotinamide phosphoribosyl transferase.

  本发明涉及一种二羟基吡咯烷衍生物，可用于癌症治疗。该发明还涉及一种制备该化合物的方法。该化合物是α甘露糖苷酶的抑制剂，可能也抑制烟酰胺磷酸核糖转移酶。
• 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.