3,6-anhydro-1-azido-1,2-dideoxy-4,5-O-isopropylidene-7-O-trityl-D-allo-heptitol | 937251-03-1

• 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: 3,6-anhydro-1-azido-1,2-dideoxy-4,5-O-isopropylidene-7-O-trityl-D-allo-heptitol
• 英文别名: (3aR,4R,6S,6aS)-6-(2-azidoethyl)-2,2-dimethyl-4-(trityloxymethyl)-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole
• CAS: 937251-03-1
• 化学式: C₂₉H₃₁N₃O₄
• 分子量: 485.583
• InChiKey: VQXZUAFJYHSHKS-YYGZZXRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  51.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,6-anhydro-1-azido-1,2-dideoxy-4,5-O-isopropylidene-7-O-trityl-D-allo-heptitol 在 三氟乙酸 作用下， 以 水 、 甲苯 为溶剂， 反应 24.0h， 生成 (2R,3S,4R,5S)-2-(hydroxymethyl)-5-[2-(4-phenyltriazol-1-yl)ethyl]oxolane-3,4-diol
  参考文献：
  名称：

  1,2,3-Triazolylalkylribitol derivatives as nucleoside hydrolase inhibitors

  摘要：

  A range of novel 1,2,3-triazolylalkyiribitol derivatives were synthesized and evaluated as nucleoside hydrolase inhibitors. The most active compound (11a) has low micromolar potency and is structurally diverse from previously reported nucleoside hydrolase inhibitors, which, along with the simplicity of the chemistry involved in its synthesis, makes it a good lead for the further development of novel nucleoside hydrolase inhibitors. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.017
• 作为产物：
  描述：

  3,6-anhydro-2-deoxy-4,5-O-isopropylidene-1-O-(methylsulfonyl)-7-O-trityl-D-allo-heptitol 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以83%的产率得到3,6-anhydro-1-azido-1,2-dideoxy-4,5-O-isopropylidene-7-O-trityl-D-allo-heptitol
  参考文献：
  名称：

  1,2,3-Triazolylalkylribitol derivatives as nucleoside hydrolase inhibitors

  摘要：

  A range of novel 1,2,3-triazolylalkyiribitol derivatives were synthesized and evaluated as nucleoside hydrolase inhibitors. The most active compound (11a) has low micromolar potency and is structurally diverse from previously reported nucleoside hydrolase inhibitors, which, along with the simplicity of the chemistry involved in its synthesis, makes it a good lead for the further development of novel nucleoside hydrolase inhibitors. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.017

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.
• 1,2,3-Triazolylalkylribitol 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、S. Apers、A. Haemers、K. Augustyns

  DOI：10.1016/j.bmcl.2007.02.017

  日期：2007.5

  A range of novel 1,2,3-triazolylalkyiribitol derivatives were synthesized and evaluated as nucleoside hydrolase inhibitors. The most active compound (11a) has low micromolar potency and is structurally diverse from previously reported nucleoside hydrolase inhibitors, which, along with the simplicity of the chemistry involved in its synthesis, makes it a good lead for the further development of novel nucleoside hydrolase inhibitors. (C) 2007 Elsevier Ltd. All rights reserved.