(2R,3R,4R,5S)-1-(6-(3-(3H-1,2,3-triazol-4-yl)phenoxy)hexyl)-2-(hydroxymethyl)piperidine-3,4,5-triol | 1017579-71-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (2R,3R,4R,5S)-1-(6-(3-(3H-1,2,3-triazol-4-yl)phenoxy)hexyl)-2-(hydroxymethyl)piperidine-3,4,5-triol
• 英文别名: (2R,3R,4R,5S)-2-(hydroxymethyl)-1-[6-[3-(2H-triazol-4-yl)phenoxy]hexyl]piperidine-3,4,5-triol
• CAS: 1017579-71-3
• 化学式: C₂₀H₃₀N₄O₅
• 分子量: 406.482
• InChiKey: RXTFDMXGUDWPDQ-IYWMVGAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  135
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N-(6-(3-ethynylphenoxy)hexyl)-2,3,4,6-tetra-O-acetyl-1,5-dideoxy-1,5-imino-D-glucitol 在 palladium on activated charcoal 苄基叠氮 、 sodium methylate 、 盐酸 、 氢气 作用下， 以 甲苯 、 甲醇 为溶剂， 反应 48.0h， 以100%的产率得到(2R,3R,4R,5S)-1-(6-(3-(3H-1,2,3-triazol-4-yl)phenoxy)hexyl)-2-(hydroxymethyl)piperidine-3,4,5-triol
  参考文献：
  名称：

  Hybrids of 1-deoxynojirimycin and aryl-1,2,3-triazoles and biological studies related to angiogenesis

  摘要：

  Hybrids of 1-deoxynojirimycin (DNJ) and aryl-1,2,3-triazole have been synthesized with a view to identifying an inhibitor of both alpha-glucosidase and methionine aminopeptidase 2 (MetAP2). One compound was a potent inhibitor of alpha-glucosidase at both the enzyme and cellular level, and this agent also inhibited bovine aortic endothelial cell (BAEC) growth and tube formation. The anti-proliferative activity of this hybrid is due to its ability to induce cell-cycle arrest in the G(1) phase. The novel agent caused a reduction in the expression of cyclin D1 but did not promote apoptosis or inhibit the phosphorylation of ERK1/ 2. These observations indicate that its mechanism of action is distinct from fumagillin and its analogues, which inhibit MetAP2. Stress-fibre assembly in BAECs was abolished by the novel agent indicating that the inhibition of BAEC tube formation observed is partially a result of a reduction in cell motility. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.012

文献信息

• Hybrid angiogenesis inhibitors: Synthesis and biological evaluation of bifunctional compounds based on 1-deoxynojirimycin and aryl-1,2,3-triazoles
  作者：Ying Zhou、Yunxue Zhao、Kathy M. O’ Boyle、Paul V. Murphy

  DOI：10.1016/j.bmcl.2007.12.034

  日期：2008.2

  Synthesis of hybrids of 1-deoxynojirimycin (DNJ) and 5-aryl-1,2,3-triazole as potential bifunctional inhibitors of angiogenesis is described. The DNJ component inhibits the biosynthesis of cell surface oligosaccharides necessary for angiogenesis, whereas the aryl-1,2,3-triazole inhibits methionine aminopeptidase II, a target in angiogenesis therapy. One bifunctional compound was a more potent inhibitor

  描述了作为潜在的双功能血管生成抑制剂的1-脱氧野oji霉素（DNJ）和5-芳基-1,2,3-三唑的杂化物的合成。DNJ成分抑制了血管生成所需的细胞表面寡糖的生物合成，而芳基1,2,3-三唑则抑制了蛋氨酸氨基肽酶II（血管生成治疗的靶标）。与单独使用DNJ或单独使用5-芳基-1,2,3-三唑相比，一种双功能化合物在体外是更有效的血管生成抑制剂。
• Hybrids of 1-deoxynojirimycin and aryl-1,2,3-triazoles and biological studies related to angiogenesis
  作者：Yunxue Zhao、Ying Zhou、Kathy M. O’Boyle、Paul V. Murphy

  DOI：10.1016/j.bmc.2008.05.012

  日期：2008.6

  Hybrids of 1-deoxynojirimycin (DNJ) and aryl-1,2,3-triazole have been synthesized with a view to identifying an inhibitor of both alpha-glucosidase and methionine aminopeptidase 2 (MetAP2). One compound was a potent inhibitor of alpha-glucosidase at both the enzyme and cellular level, and this agent also inhibited bovine aortic endothelial cell (BAEC) growth and tube formation. The anti-proliferative activity of this hybrid is due to its ability to induce cell-cycle arrest in the G(1) phase. The novel agent caused a reduction in the expression of cyclin D1 but did not promote apoptosis or inhibit the phosphorylation of ERK1/ 2. These observations indicate that its mechanism of action is distinct from fumagillin and its analogues, which inhibit MetAP2. Stress-fibre assembly in BAECs was abolished by the novel agent indicating that the inhibition of BAEC tube formation observed is partially a result of a reduction in cell motility. (c) 2008 Elsevier Ltd. All rights reserved.