2,3,4,6-tetra-O-propionyl-β-D-glucopyranosyl azide | 1417909-30-8

• 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: 2,3,4,6-tetra-O-propionyl-β-D-glucopyranosyl azide
• 英文别名: [(2R,3R,4S,5R,6R)-6-azido-3,4,5-tri(propanoyloxy)oxan-2-yl]methyl propanoate
• CAS: 1417909-30-8
• 化学式: C₁₈H₂₇N₃O₉
• 分子量: 429.427
• InChiKey: FPIUYLSTLASWBR-LUAGPVBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-propionyl-β-D-glucopyranosyl azide 、 4-乙炔基苯磺酰胺 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 乙醇 、 水 为溶剂， 反应 3.5h， 以76%的产率得到4-[4-(aminosulfonyl)phenyl]-1-(2,3,4,6-tetra-O-propionyl-β-D-glucopyranosyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  A Prodrug Approach Toward Cancer-Related Carbonic Anhydrase Inhibition

  摘要：

  The selective inhibition of cancer-associated human carbonic anhydrase (CA) enzymes, specifically CA IX and XII, has been validated as a mechanistically novel approach toward personalized cancer management. Herein we report the design and synthesis of a panel of 24 novel glycoconjugate primary sulfonamides that bind to the extracellular catalytic domain of CA IX and XII. These compounds were synthesized from variably acylated glycopyranosyl azides and either 3- or 4-ethynyl benzene sulfonamide using Cu(I)-catalyzed azide alkyne cycloaddition (CuAAC). The CA enzyme inhibition profile for all compounds was determined, while in vitro metabolic stability, plasma stability, and plasma protein binding for a representative set of compounds was measured. Our findings demonstrate the influence of the differing acyl groups on these key biopharmaceutical properties, confirming that acyl group protected carbohydrate-based sulfonamides have potential as prodrugs for selectively targeting the extracellular cancer-associated CA enzymes.

  DOI：

  10.1021/jm401163e
• 作为产物：
  描述：

  1,2,3,4,6-penta-O-propionyl-D-glucopyranose 在 叠氮基三甲基硅烷 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 2,3,4,6-tetra-O-propionyl-β-D-glucopyranosyl azide
  参考文献：
  名称：

  Synthesis of acylated glycoconjugates as templates to investigate in vitro biopharmaceutical properties

  摘要：

  A series of novel glycopyranosyl azides were synthesised wherein the carbohydrate moiety was peracylated with four acetyl, propionyl, butanoyl, pentanoyl (valeryl) or 3-methylbutanoyl (isovaleryl) ester linked groups. A panel of glycoconjugates was synthesised from these glycopyranosyl azides using copper-catalysed azide-alkyne cycloaddition. The in vitro metabolic stability, plasma stability and plasma protein binding was then measured to establish the impact of the different acyl group when presented on a common scaffold. The acetyl, propionyl and butanoyl esters exhibited metabolism consistent with esterase processing, and various mono-, di- and tri-acylated hydrolysis products as well as the fully hydrolysed compound were detected. In contrast, the pentanoyl and 3-methylbutanoyl esters were stable. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.056

文献信息

• Ruthenium tetrazene complexes bearing glucose moieties on their periphery: Synthesis, characterization, and <i>in vitro</i> cytotoxicity
  作者：Vojtěch Hamala、Andrea Martišová、Lucie Červenková Šťastná、Jindřich Karban、Andrej Dančo、Adam Šimarek、Martin Lamač、Michal Horáček、Tamara Kolářová、Roman Hrstka、Róbert Gyepes、Jiří Pinkas

  DOI：10.1002/aoc.5896

  日期：2020.11

  ed (5a), and O‐acetylated (5b), were synthesized and characterized using nuclear magnetic resonance and electrospray ionization–mass spectrometry. In addition, the molecular structure of 3b was determined using X‐ray crystallography. The cytotoxicity of complexes against ovarian (A2780, SK‐OV‐3) and breast (MDA‐MB‐231) cancer cell lines and noncancerous cell line HEK‐293 was evaluated and compared

  钌配合物四氮烯与通式的[CP *的RuCl（1,4-R 2 Ñ 4）]（CP * =η 5 -C 5我5），其中R =苄基（1），2-氟苄基（2），β - d吡喃葡萄糖基未保护的（图3a）和酰基保护的（图3b - d），2-乙酰氨基β - d吡喃葡萄糖基未保护的（图4a）和酰基保护的（4B - d），丙基- β - d吡喃葡萄糖苷不受保护（5a），以及使用核磁共振和电喷雾电离质谱对O-乙酰化（5b）进行了合成和表征。此外，使用X射线晶体学测定了3b的分子结构。评估了复合物对卵巢癌（A2780，SK‐OV‐3）和乳腺癌（MDA‐MB‐231）和非癌细胞系HEK‐293的细胞毒性并将其与顺铂活性进行了比较。碳水化合物改性的复合轴承酰基保护基团表现出比未保护的，其中最活跃的更高的效力（在低摩尔范围）4D在所有研究的癌细胞系中，它比顺铂高出五倍；但是，没有达到明显的选择性。该复合物在低微摩尔浓度下