2-(β-D-glucopyranosyl)-1,4-dimethoxynaphthalene | 915716-23-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(β-D-glucopyranosyl)-1,4-dimethoxynaphthalene
• 英文别名: (2S,3R,4R,5S,6R)-2-(1,4-dimethoxynaphthalen-2-yl)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 915716-23-3
• 化学式: C₁₈H₂₂O₇
• 分子量: 350.368
• InChiKey: KMSZJMGSIMXJRE-QFXBJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  109
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(β-D-glucopyranosyl)-1,4-dimethoxynaphthalene 在 4-二甲氨基吡啶 、 copper(ll) sulfate pentahydrate 、 sodium hydride 、 sodium ascorbate 、 乙酰氯 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 3,4-di-O-{1-[1(S)-methoxycarbonyl-2-phenylethyl]-4-methyl-1H-1,2,3-triazol-4-yl}-β-D-glucopyranosyl 1,4-dimethoxynaphthalene
  参考文献：
  名称：

  Discovery of a sensitive Cu(ii)-cyanide “off–on” sensor based on new C-glycosyl triazolyl bis-amino acid scaffold

  摘要：

  通过点击化学，我们很容易合成了一种新的功能性糖基肽模拟物，其特点是在相邻的 C3、4 位上以 C-葡萄糖基 1,4-二甲氧基萘为骨架与两个三唑基苯丙氨酸共轭。初级光学测量结果表明，这种探针的酯形式（4）的荧光可被 Pb2+ 选择性地淬灭。相比之下，其类似物 5 带有释放的羧基，其荧光强度被 Cu2+ 独特地减弱，灵敏度和选择性显著提高。此外，在生成的 Cu2+-5 复合物的甲醇溶液中随后加入氰化物，可诱导其荧光恢复，检测限为纳摩尔，比饮用水中 CNâ 的规定浓度限小两个数量级。这表明，C-糖基双三唑基氨基酸支架在未来设计和探索灵敏的氰化铜（II）化学传感器方面具有广阔的应用前景。

  DOI：

  10.1039/c1ob06242e
• 作为产物：
  描述：

  2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,4-dimethoxynaphthalene 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以97%的产率得到2-(β-D-glucopyranosyl)-1,4-dimethoxynaphthalene
  参考文献：
  名称：

  Synthesis of β-C-glycopyranosyl-1,4-naphthoquinone derivatives and their cytotoxic activity

  摘要：

  beta-C-Glucosyl and beta-C-galactosyl-1,4-dimethoxynaphthalenes have been synthesized using a F3CCO2Ag/SnCl4 promoted Friedel-Crafts electrophilic substitution reaction. Both glycosyl acetates and methyl glycosides can be used as glycosyl donors. Further oxidation afforded the corresponding beta-C-glycosyl-1,4-naphthoquinones. The in vitro cytotoxic activity of these compounds was evaluated against the A375 cell line. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.12.017

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.
• 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.