N,N'-bis(tert-butoxycarbonyl)-1-guanidino-2,5-anhydro-3,4,6-tri-O-benzoyl-1-deoxy-D-allitol | 1020107-15-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N,N'-bis(tert-butoxycarbonyl)-1-guanidino-2,5-anhydro-3,4,6-tri-O-benzoyl-1-deoxy-D-allitol
• 英文别名: [(2R,3R,4S,5S)-3,4-dibenzoyloxy-5-[[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]methyl]oxolan-2-yl]methyl benzoate
• CAS: 1020107-15-6
• 化学式: C₃₈H₄₃N₃O₁₁
• 分子量: 717.773
• InChiKey: VVENUBQGKOJXLZ-RRGQHJHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  52
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  177
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N,N'-bis(tert-butoxycarbonyl)-1-guanidino-2,5-anhydro-3,4,6-tri-O-benzoyl-1-deoxy-D-allitol 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 18.0h， 以100%的产率得到1-guanidino-2,5-anhydro-3,4,6-tri-O-benzoyl-1-deoxy-D-allitol trifluoroacetate
  参考文献：
  名称：

  Synthesis and biochemical evaluation of guanidino-alkyl-ribitol derivatives as nucleoside hydrolase inhibitors

  摘要：

  Nucleoside hydrolase (NH) is a key enzyme in the purine salvage pathway. The purine specificity of the IAG-NH from Trypanosoma vivax is at least in part due to cation-pi-stacking interactions. Guanidinium ions can be involved in cation-pi-stacking interactions, therefore a series of guanidino-alkyl-ribitol derivatives were synthesized in order to examine the binding affinity of these compounds towards the target enzyme. The compounds show moderate to good inhibiting activity towards the IAG-NH from T. vivax. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.03.027
• 作为产物：
  描述：

  1-amino-2,5-anhydro-3,4,6-tri-O-benzoyl-1-deoxy-D-allitol 、 1-[(tert-butyloxycarbonylamino)-(tert-butyloxycarbonylimino)-methyl]-1H-pyrazole 以 氯仿 为溶剂， 反应 24.0h， 以22%的产率得到N,N'-bis(tert-butoxycarbonyl)-1-guanidino-2,5-anhydro-3,4,6-tri-O-benzoyl-1-deoxy-D-allitol
  参考文献：
  名称：

  Synthesis and biochemical evaluation of guanidino-alkyl-ribitol derivatives as nucleoside hydrolase inhibitors

  摘要：

  Nucleoside hydrolase (NH) is a key enzyme in the purine salvage pathway. The purine specificity of the IAG-NH from Trypanosoma vivax is at least in part due to cation-pi-stacking interactions. Guanidinium ions can be involved in cation-pi-stacking interactions, therefore a series of guanidino-alkyl-ribitol derivatives were synthesized in order to examine the binding affinity of these compounds towards the target enzyme. The compounds show moderate to good inhibiting activity towards the IAG-NH from T. vivax. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.03.027

文献信息

• Synthesis and biochemical evaluation of guanidino-alkyl-ribitol derivatives as nucleoside hydrolase inhibitors
  作者：A. Goeminne、M. McNaughton、G. Bal、G. Surpateanu、P. Van Der Veken、S. De Prol、W. Versées、J. Steyaert、A. Haemers、K. Augustyns

  DOI：10.1016/j.ejmech.2007.03.027

  日期：2008.2

  Nucleoside hydrolase (NH) is a key enzyme in the purine salvage pathway. The purine specificity of the IAG-NH from Trypanosoma vivax is at least in part due to cation-pi-stacking interactions. Guanidinium ions can be involved in cation-pi-stacking interactions, therefore a series of guanidino-alkyl-ribitol derivatives were synthesized in order to examine the binding affinity of these compounds towards the target enzyme. The compounds show moderate to good inhibiting activity towards the IAG-NH from T. vivax. (c) 2007 Elsevier Masson SAS. All rights reserved.