2-(4-hydroxyphenyl)ethyl 2-acetamido-2-deoxy-β-D-glucopyranoside | 1338496-34-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-hydroxyphenyl)ethyl 2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: GlcNAc(b)-O-EtPh(4-OH)；N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[2-(4-hydroxyphenyl)ethoxy]oxan-3-yl]acetamide
• CAS: 1338496-34-6
• 化学式: C₁₆H₂₃NO₇
• 分子量: 341.361
• InChiKey: MGWKDXFWOJHSEJ-OXGONZEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  129
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(4-hydroxyphenyl)ethyl 2-acetamido-2-deoxy-β-D-glucopyranoside 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以88%的产率得到(2R,3S,4R,5R,6R)-5-amino-2-(hydroxymethyl)-6-[2-(4-hydroxyphenyl)ethoxy]oxane-3,4-diol
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Two Salidroside Analogues in the PC12 Cell Model Exposed to Hypoglycemia and Serum Limitation

  摘要：

  Salidroside 是一种从红景天（Rhodiola rosea L.）中分离得到的苯丙烷糖苷，这是一种传统的中药植物，显示了广泛的药理特性。本文中制备了两种类似物，使用氨基葡萄糖和N-乙酰氨基葡萄糖作为糖基供体，2-(4-羟基苯基)乙醇作为糖基受体。通过3-(4,5-二甲基噻唑-2-基)-2,5-二苯基四唑溴化物（MTT）实验、流式细胞术和西方 blot 分析评估了它们对暴露于缺糖和血清限制的PC12细胞模型的影响。

  DOI：

  10.1248/cpb.59.1045
• 作为产物：
  描述：

  2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranosyl chloride 在 5%-palladium/activated carbon 、 4,4'-双甲氧基三苯甲基氯 、 甲酸铵 、 sodium methylate 、 zinc(II) chloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 2-(4-hydroxyphenyl)ethyl 2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Two Salidroside Analogues in the PC12 Cell Model Exposed to Hypoglycemia and Serum Limitation

  摘要：

  Salidroside 是一种从红景天（Rhodiola rosea L.）中分离得到的苯丙烷糖苷，这是一种传统的中药植物，显示了广泛的药理特性。本文中制备了两种类似物，使用氨基葡萄糖和N-乙酰氨基葡萄糖作为糖基供体，2-(4-羟基苯基)乙醇作为糖基受体。通过3-(4,5-二甲基噻唑-2-基)-2,5-二苯基四唑溴化物（MTT）实验、流式细胞术和西方 blot 分析评估了它们对暴露于缺糖和血清限制的PC12细胞模型的影响。

  DOI：

  10.1248/cpb.59.1045

文献信息

• Synthesis and protective effects of aralkyl alcoholic 2-acetamido-2-deoxy-β-d-pyranosides on hypoglycemia and serum limitation induced apoptosis in PC12 cell
  作者：Ying Meng、Yibing Guo、Yong Ling、Yahong Zhao、Qi Zhang、Xinyang Zhou、Fei Ding、Yumin Yang

  DOI：10.1016/j.bmc.2011.07.031

  日期：2011.9

  Neuroprotective agents have been in the focus of attention in the treatment of ischemic stroke. Salidroside, a phenylpropanoid glycoside isolated from Rhodiola rosea L., possessed a wide range of biological activities, especially neuroprotection. In an attempt to improve neuroprotective effects of new salidroside analogs for ischemic stroke, a series of novel aralkyl alcoholic 2-acetamido-2-deoxy-beta-D-pyranosides were synthesized and their protective activities against the hypoglycemia and serum limitation induced cell death in rat pheochromocytoma cells (PC12 cells) were studied. Most compounds showed strong neuroprotective effects, especially for 4g and 4h, which exhibited a great potency superior to salidroside. MTT assay, Hoechst 33342 staining, and flow cytometry with annexin V/PI staining collectively showed that pretreatment with 4g and 4h attenuated cell viability loss and apoptotic cell death in cultured PC12 cells. Caspase-3 colorimetric assay and Rhodamine 123 staining revealed the changes in expression levels of caspase-3 and mitochondrial membrane potential in PC12 cells on exposure to hypoglycemia and serum limitation with and without 4g and 4h pretreatment, respectively. All the results suggested that 4g and 4h protects the PC12 cells against hypoglycemia and serum limitation induced apoptosis possibly by modulation of apoptosis-related gene expression and restoration of the mitochondrial membrane potential. Therefore, these novel findings may provided a new framework for the design of new aralkyl alcoholic 2-acetamido-2-deoxy-beta-D-pyranosides as neuroprotective agents for treating cerebral ischemic stroke and neurodegenerative diseases. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and Biological Evaluation of Two Salidroside Analogues in the PC12 Cell Model Exposed to Hypoglycemia and Serum Limitation
  作者：Yibing Guo、Xiaohong Li、Yahong Zhao、Yongxing Si、Hui Zhu、Yumin Yang

  DOI：10.1248/cpb.59.1045

  日期：——

  Salidroside is a phenylpropanoid glycoside isolated from Rhodiola rosea L., a traditional Chinese medicinal plant, and has displayed a broad spectrum of pharmacological properties. In this paper, two analogues were prepared with the glucosamine and N-acetylglucosamine as glycosyl donor, 2-(4-hydroxyphenyl)ethanol as glycosyl acceptor. The effects of them over PC12 cell model exposed to hypoglycemia and serum limitation were assessed with 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay, Flow Cytometry and Western blot analysis.

  Salidroside 是一种从红景天（Rhodiola rosea L.）中分离得到的苯丙烷糖苷，这是一种传统的中药植物，显示了广泛的药理特性。本文中制备了两种类似物，使用氨基葡萄糖和N-乙酰氨基葡萄糖作为糖基供体，2-(4-羟基苯基)乙醇作为糖基受体。通过3-(4,5-二甲基噻唑-2-基)-2,5-二苯基四唑溴化物（MTT）实验、流式细胞术和西方 blot 分析评估了它们对暴露于缺糖和血清限制的PC12细胞模型的影响。