phenyl 2,3-di-O-acetyl-6-O-benzoyl-1-thio-β-D-glucopyranoside | 257614-51-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3-di-O-acetyl-6-O-benzoyl-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-4,5-diacetyloxy-3-hydroxy-6-phenylsulfanyloxan-2-yl]methyl benzoate
• CAS: 257614-51-0
• 化学式: C₂₃H₂₄O₈S
• 分子量: 460.505
• InChiKey: MVPXTQQLJOABOB-VZWAGXQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  phenyl 2,3-di-O-acetyl-6-O-benzoyl-1-thio-β-D-glucopyranoside 在 三氯异氰尿酸 、 水 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 1.83h， 生成
  参考文献：
  名称：

  Synthesis, biological evaluation and structure-activity relationship studies of hederacolchiside E and its derivatives as potential anti-Alzheimer agents

  摘要：

  Inspired by the previously reported neuroprotective activity of hederacolchiside E (1), we synthesized hederacolchiside E for the first time along with eleven of its derivatives. The neuroprotective effects of these compounds were further evaluated against H2O2- and A beta(1-42)-induced injury using cell-based assays. The derivatives showed obvious differences in activity due to structural variations, and two of them exhibited better neuroprotective effects than 1 in the A beta(1-42)-induced injury model. Compound 7 was the most active derivative and had a relatively simple chemical structure. Moreover, 1 and 7 can significantly reduce the release of lactate dehydrogenase (LDH), level of intracellular reactive oxygen species (ROS) and extent of malondialdehyde (MDA) increase resulting from A beta(1-42) treatment, which demonstrated that these kinds of compounds show neuroprotective effects in Alzheimer's disease (AD) models via modulating oxidative stress. Compound 7 could be used as promising lead for the development of a new type of neuroprotective agent against AD. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.11.040
• 作为产物：
  描述：

  苯基-4,6-O-苯亚甲基-1-硫代-Β-D-吡喃葡萄糖苷 在 吡啶 、 溶剂黄146 作用下， 生成 phenyl 2,3-di-O-acetyl-6-O-benzoyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  First Synthesis of a Bidesmosidic Triterpene Saponin by a Highly Efficient Procedure

  摘要：

  DOI：

  10.1021/ja9926818