N,N'-(tert-butoxycarbonyl)-1-guanidino-4,7-anhydro-1,2,3-trideoxy-5,6-O-isopropylidene-8-O-trityl-D-allo-octitol | 1020107-21-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N,N'-(tert-butoxycarbonyl)-1-guanidino-4,7-anhydro-1,2,3-trideoxy-5,6-O-isopropylidene-8-O-trityl-D-allo-octitol
• 英文别名: tert-butyl N-[N'-[1-[(3aR,4R,6S,6aS)-2,2-dimethyl-4-(trityloxymethyl)-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]propan-2-yl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamate
• CAS: 1020107-21-4
• 化学式: C₄₁H₅₃N₃O₈
• 分子量: 715.887
• InChiKey: CFMSHRLEYKGEOH-PLWWYYEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  52
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N,N'-(tert-butoxycarbonyl)-1-guanidino-4,7-anhydro-1,2,3-trideoxy-5,6-O-isopropylidene-8-O-trityl-D-allo-octitol 、 三氟乙酸 在 水 作用下， 反应 18.0h， 以44%的产率得到1-guanidino-4,7-anhydro-1,2,3-trideoxy-D-allo-octitol 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：

  4,7-anhydro-2-amino-1,2,3-trideoxy-5,6-O-isopropylidene-8-O-trityl-D-allo-octitol 、 1-[(tert-butyloxycarbonylamino)-(tert-butyloxycarbonylimino)-methyl]-1H-pyrazole 以 氯仿 为溶剂， 反应 24.0h， 以20%的产率得到N,N'-(tert-butoxycarbonyl)-1-guanidino-4,7-anhydro-1,2,3-trideoxy-5,6-O-isopropylidene-8-O-trityl-D-allo-octitol
  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.