(2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(4-(4-aminophenyl)-1H-1,2,3-triazol-1-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate | 1233043-65-6

• 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: (2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(4-(4-aminophenyl)-1H-1,2,3-triazol-1-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• 英文别名: 1-(4-(4-aminophenyl)-[1,2,3]-triazol-1-yl)-2,3,4,6-tetra-O-acetyl-1-deoxy-β-D-galactopyranoside
• CAS: 1233043-65-6
• 化学式: C₂₂H₂₆N₄O₉
• 分子量: 490.47
• InChiKey: PSNRDRZJEBODQH-CDJZJNNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.78
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  171.16
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(4-(4-aminophenyl)-1H-1,2,3-triazol-1-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 甲醇 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 4-[1-(β-D-galactopyranosyl)-1H-1,2,3-triazol-4-yl]-aniline
  参考文献：
  名称：

  ‘Click chemistry’ synthesis of a library of 1,2,3-triazole-substituted galactose derivatives and their evaluation against Trypanosoma cruzi and its cell surface trans-sialidase

  摘要：

  Trypanosoma cruzi trans-sialidase (TcTS) plays a key role in the recognition and invasion of host cells and in enabling the parasite to escape the human immune response. To explore this potential drug target, we have synthesized a small library of substrate analogues based on 1,4-disubstituted 1,2,3-triazole derivatives of galactose modified at either the C-1 or C-6 positions. This was achieved by coupling the appropriate azido-sugars with a panel of 23 structurally diverse terminal alkynes by using the copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) reaction, giving a library of 46 derivatives in good to excellent yield and with complete regioselectivity. The sugar triazoles showed weak inhibition towards TcTS-catalyzed hydrolysis of 2'-(4-methylumbelliferyl)-alpha-D-N-acetylneuraminic acid in vitro (<40% inhibition at 1 mM concentration); many of the compounds assessed proved to be acceptor substrates for the enzyme. Despite this modest inhibitory activity, in vitro trypanocidal activity assays against the trypomastigote form of T. cruzi Y strain revealed several compounds active in the low 100s of mu M range. Further assessment of these compounds against cultured mouse spleen cells suggests a specific mode of anti-parasite action rather than a generic cytotoxic effect. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.02.053
• 作为产物：
  描述：

  1-(4-(4-nitrophenyl)-[1,2,3]-triazol-1-yl)-2,3,4,6-tetra-O-acetyl-1-deoxy-β-D-galactopyranoside 在 溶剂黄146 、 锌 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以91%的产率得到(2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(4-(4-aminophenyl)-1H-1,2,3-triazol-1-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  聚脯氨酸肽支架上支持的二价半乳糖苷开发铜绿假单胞菌凝集素LecA抑制剂

  摘要：

  LecA是一种来自铜绿假单胞菌的半乳糖结合四聚体凝集素，参与感染和生物膜形成。铜绿假单胞菌的紧急耐药性LecA已成为治疗此类感染的有希望的药物靶标。为了开发LecA抑制剂，我们利用了聚脯氨酸肽的独特螺旋结构来创建一个支架，该支架控制半乳糖苷的位置以适合其在LecA上的结合位点。通过模块化支架设计，可以方便地更改半乳糖苷配体和配体间的距离。我们准备了间距为9、18、27和36的支架进行配体缀合，发现具有半乳糖苷配体的糖肽相距三个螺旋圈（27Å）最适合LecA。此外，我们在所选支架（27Å）上测试了不同的半乳糖衍生物，以改善与LecA的结合亲和力。结果验证了新的多价支架设计，并为LecA抑制剂的开发提供了有用的信息。

  DOI：

  10.1002/asia.201701724