1-(3,5-dimethoxyphenyl)methyl 2-acetamido-2-deoxy-β-D-glucopyranoside | 1338496-28-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3,5-dimethoxyphenyl)methyl 2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: N-[(2R,3R,4R,5S,6R)-2-[(3,5-dimethoxyphenyl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 1338496-28-8
• 化学式: C₁₇H₂₅NO₈
• 分子量: 371.387
• InChiKey: WUDIIVAYBBCJFV-WRQOLXDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  127
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以95%的产率得到1-(3,5-dimethoxyphenyl)methyl 2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and protective effects of aralkyl alcoholic 2-acetamido-2-deoxy-β-d-pyranosides on hypoglycemia and serum limitation induced apoptosis in PC12 cell

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2011.07.031

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.