bis((1-(((2R,3R,4R,5S,6S)-3,4,5-tris(benzoyloxy)-6-(2,5-dimethoxyphenyl)-tetrahydro-2H-pyran-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl) isophthalate | 1093850-46-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: bis((1-(((2R,3R,4R,5S,6S)-3,4,5-tris(benzoyloxy)-6-(2,5-dimethoxyphenyl)-tetrahydro-2H-pyran-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl) isophthalate
• 英文别名: bis[[1-[[(2R,3R,4R,5S,6S)-3,4,5-tribenzoyloxy-6-(2,5-dimethoxyphenyl)oxan-2-yl]methyl]triazol-4-yl]methyl] benzene-1,3-dicarboxylate
• CAS: 1093850-46-4
• 化学式: C₈₄H₇₂N₆O₂₂
• 分子量: 1517.52
• InChiKey: FZOZCEQDTORGJJ-OXVJGABRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.1
• 重原子数：
  112
• 可旋转键数：
  36
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  327
• 氢给体数：
  0
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  bis((1-(((2R,3R,4R,5S,6S)-3,4,5-tris(benzoyloxy)-6-(2,5-dimethoxyphenyl)-tetrahydro-2H-pyran-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl) isophthalate 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以95%的产率得到bis((1-(((2R,3R,4R,5S,6S)-3,4,5-tris(benzoyloxy)-6-(3,6-dioxocyclohexa-1,4-dienyl)-tetrahydro-2H-pyran-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl) isophthalate
  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-(6'-azido-2',3',4'-tri-O-benzoyl-6'-deoxy-β-D-glucopyranosyl)-1,4-dimethoxybenzene 、 Isophthalsaeure-dipropargylester 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 为溶剂， 以94%的产率得到bis((1-(((2R,3R,4R,5S,6S)-3,4,5-tris(benzoyloxy)-6-(2,5-dimethoxyphenyl)-tetrahydro-2H-pyran-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl) isophthalate
  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

• Synthesis of triazole-linked β-C-glycosyl dimers as inhibitors of PTP1B
  作者：Li Lin、Qiang Shen、Guo-Rong Chen、Juan Xie

  DOI：10.1016/j.bmc.2008.09.066

  日期：2008.11

  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.