bis[[1-[[(2R,3S,4R,5S,6S)-3,4,5-triacetyloxy-6-(1,4-dimethoxynaphthalen-2-yl)oxan-2-yl]methyl]triazol-4-yl]methyl] benzene-1,3-dicarboxylate | 1093850-51-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: bis[[1-[[(2R,3S,4R,5S,6S)-3,4,5-triacetyloxy-6-(1,4-dimethoxynaphthalen-2-yl)oxan-2-yl]methyl]triazol-4-yl]methyl] benzene-1,3-dicarboxylate
• CAS: 1093850-51-1
• 化学式: C₆₂H₆₄N₆O₂₂
• 分子量: 1245.22
• InChiKey: HDFKZDVFTCSHGB-RODKSOJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.79
• 重原子数：
  90.0
• 可旋转键数：
  22.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  327.2
• 氢给体数：
  0.0
• 氢受体数：
  28.0

反应信息

• 作为反应物：
  描述：

  bis[[1-[[(2R,3S,4R,5S,6S)-3,4,5-triacetyloxy-6-(1,4-dimethoxynaphthalen-2-yl)oxan-2-yl]methyl]triazol-4-yl]methyl] benzene-1,3-dicarboxylate 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以56%的产率得到bis[[1-[[(2R,3S,4R,5S,6S)-3,4,5-triacetyloxy-6-(1,4-dioxonaphthalen-2-yl)oxan-2-yl]methyl]triazol-4-yl]methyl] benzene-1,3-dicarboxylate
  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-acetyl-6'-azido-6'-deoxy-β-D-galactopyranosyl)-1,4-dimethoxynaphthalene 、 Isophthalsaeure-dipropargylester 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 为溶剂， 以95%的产率得到bis[[1-[[(2R,3S,4R,5S,6S)-3,4,5-triacetyloxy-6-(1,4-dimethoxynaphthalen-2-yl)oxan-2-yl]methyl]triazol-4-yl]methyl] benzene-1,3-dicarboxylate
  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