2,3,4,6-tetra-O-pentanoyl-β-D-glucopyranosyl azide | 1417909-32-0

• 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-pentanoyl-β-D-glucopyranosyl azide
• 英文别名: [(2R,3R,4S,5R,6R)-6-azido-3,4,5-tri(pentanoyloxy)oxan-2-yl]methyl pentanoate
• CAS: 1417909-32-0
• 化学式: C₂₆H₄₃N₃O₉
• 分子量: 541.642
• InChiKey: RZEACZPECKXFEQ-ABNLYDASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  38
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 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-pentanoyl-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 144.0h， 以57%的产率得到4-[4-(aminosulfonyl)phenyl]-1-(2,3,4,6-tetra-O-pentyryl-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-azido-1-deoxy-β-D-glucopyranoside tetraacetate 在 吡啶 、 甲醇 、 sodium methylate 作用下， 生成 2,3,4,6-tetra-O-pentanoyl-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