2-(2',3',4'-tri-O-benzoyl-β-D-glucopyranosyl)-1,4-dimethoxybenzene | 1093850-30-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2',3',4'-tri-O-benzoyl-β-D-glucopyranosyl)-1,4-dimethoxybenzene
• 英文别名: [(2R,3R,4R,5S,6S)-4,5-dibenzoyloxy-6-(2,5-dimethoxyphenyl)-2-(hydroxymethyl)oxan-3-yl] benzoate
• CAS: 1093850-30-6
• 化学式: C₃₅H₃₂O₁₀
• 分子量: 612.633
• InChiKey: GJALMVYOJCKLAV-OXFURMMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  45
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-(2',3',4'-tri-O-benzoyl-β-D-glucopyranosyl)-1,4-dimethoxybenzene 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of triazole-linked β-C-glycosyl dimers as inhibitors of PTP1B

  摘要：

  Protein tyrosine phosphatase 1B (PTP1B) has emerged as a promising target for type 2 diabetes. We have successfully synthesized dimeric acetylated and benzoylated beta-C-D-glucosyl and beta-C-D-galactosyl 1,4-dimethoxy benzenes or naphthalenes by click chemistry. These compounds were further transformed into the corresponding beta-C-D-glycosyl-1,4-quinone derivatives by CAN oxidation. The in vitro inhibition test showed that dimeric benzoylated beta-C-D-glycosyl 1,4-dimethoxybenzenes or 1,4-benzoquinones were good inhibitors of PTP1B (IC50: 0.62-0.88 mu M), with no significant difference between gluco and galacto derivatives. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.066
• 作为产物：
  描述：

  2-(2',3',4'-tri-O-benzoyl-6'-O-triphenylmethyl-β-D-glucopyranosyl)-1,4-dimethoxybenzene 在 水 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以79%的产率得到2-(2',3',4'-tri-O-benzoyl-β-D-glucopyranosyl)-1,4-dimethoxybenzene
  参考文献：
  名称：

  Synthesis of triazole-linked β-C-glycosyl dimers as inhibitors of PTP1B

  摘要：

  Protein tyrosine phosphatase 1B (PTP1B) has emerged as a promising target for type 2 diabetes. We have successfully synthesized dimeric acetylated and benzoylated beta-C-D-glucosyl and beta-C-D-galactosyl 1,4-dimethoxy benzenes or naphthalenes by click chemistry. These compounds were further transformed into the corresponding beta-C-D-glycosyl-1,4-quinone derivatives by CAN oxidation. The in vitro inhibition test showed that dimeric benzoylated beta-C-D-glycosyl 1,4-dimethoxybenzenes or 1,4-benzoquinones were good inhibitors of PTP1B (IC50: 0.62-0.88 mu M), with no significant difference between gluco and galacto derivatives. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.066

文献信息

• β-C-Glycosiduronic acids and β-C-glycosyl compounds: New PTP1B inhibitors
  作者：Li Lin、Qiang Shen、Guo-Rong Chen、Juan Xie

  DOI：10.1016/j.bmcl.2008.10.091

  日期：2008.12

  beta-C-Glycosiduronic acid quinones and beta-C-glycosyl compounds have been synthesized as sugar-based PTP1B inhibitors. Benzoyl protected quinone derivatives (14 and 35) as well as aryl beta-C-glycosyl compounds (18, 22, 23 and 34) showed IC50 values of 0.77-5.27 mu M against PTP1B, with compounds 18 and 23 bearing an acidic function being the most potent. (C) 2008 Elsevier Ltd. All rights reserved.