5-O-tert-butyldimethylsilyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-N-(4-aminobenzyl)-D-ribitol | 1020107-43-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-O-tert-butyldimethylsilyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-N-(4-aminobenzyl)-D-ribitol
• 英文别名: 4-[[(3aR,4R,6aS)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-5-yl]methyl]aniline
• CAS: 1020107-43-0
• 化学式: C₂₁H₃₆N₂O₃Si
• 分子量: 392.614
• InChiKey: KRPOFCVTIUIMEA-CEXWTWQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  57
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-O-tert-butyldimethylsilyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-N-(4-aminobenzyl)-D-ribitol 、 1-[(tert-butyloxycarbonylamino)-(tert-butyloxycarbonylimino)-methyl]-1H-pyrazole 以 氯仿 为溶剂， 反应 48.0h， 以11%的产率得到tert-butyl N-[N'-[4-[[(3aR,4R,6aS)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-5-yl]methyl]phenyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamate
  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：

  5-O-tert-butyldimethylsilyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-N-(4-nitrobenzyl)-D-ribitol 在 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以18%的产率得到5-O-tert-butyldimethylsilyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-N-(4-aminobenzyl)-D-ribitol
  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.