4-甲基伞形酮-Α-N-乙酰基神经氨酸苷钠盐 | 76204-02-9

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 4-甲基伞形酮-Α-N-乙酰基神经氨酸苷钠盐
• 中文别名: 4-甲基香豆素基-Α-D-唾液酸钠盐；N-乙酰基-2-O-(4-甲基-2-氧代-2H-1-苯并吡喃-7-基)-ALPHA-神经氨酸一钠盐；N-乙酰基-2-O-(4-甲基-2-氧代-2H-1-苯并吡喃-7-基)-alpha-神经氨酸一钠盐
• 英文名称: 4-MUNANA
• 英文别名: 2'-(4-methylumbelliferyl)-α-D-N-acetylneuraminic acid sodium salt；MUNANA；Sodium 4-methyl-2-oxo-2H-1-benzopyran-7-yl 3,5-dideoxy-5-[(1-oxidanidylethylidene)amino]non-2-ulopyranosidonic acid；sodium;N-[(2R,3R,4S,6S)-6-carboxy-4-hydroxy-6-(4-methyl-2-oxochromen-7-yl)oxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-3-yl]ethanimidate
• CAS: 76204-02-9
• 化学式: C₂₁H₂₄NO₁₁*Na
• 分子量: 489.411
• InChiKey: NNNXBDLJYKMDAI-NLSRWXBQSA-M

物化性质

• 熔点：
  171°C dec.
• 溶解度：
  H2O：50 mg/mL，清澈，淡黄色

计算性质

• 辛醇/水分配系数(LogP)：
  -5.7
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  195
• 氢给体数：
  5
• 氢受体数：
  11

安全信息

• 安全说明：
  S24/25
• WGK Germany：
  3
• 海关编码：
  29322090

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6R)-2-(4-benzyl-1H-1,2,3-triazol-1-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 、 4-甲基伞形酮-Α-N-乙酰基神经氨酸苷钠盐 在 crude cleared bacterial cell lysate containing Trypanosoma cruzi trans-sialidase 作用下， 以 水 为溶剂， 反应 4.0h， 生成
  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：

  (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester 在 sodium hydroxide 、 水 作用下， 以99%的产率得到4-甲基伞形酮-Α-N-乙酰基神经氨酸苷钠盐
  参考文献：
  名称：

  A Facile Access to Aryl α-Sialosides: the Combination of a Volatile Amine Base and Acetonitrile in Glycosidation of Sialosyl Chlorides

  摘要：

  我们已经成功实现了对4-硝基苯基和4-甲基伞形酮-α-唾液酸苷的简易获取。对于完全被乙酰基保护的唾液酸氯化物作为糖基供体，在乙腈中使用二异丙基乙胺作用下的酚类物质带来了高产率以及简易的产品分离。

  DOI：

  10.1055/s-1998-1717

文献信息

• Anomeric 1,2,3-triazole-linked sialic acid derivatives show selective inhibition towards a bacterial neuraminidase over a trypanosome <i>trans</i>-sialidase
  作者：Peterson de Andrade、Sanaz Ahmadipour、Robert A Field

  DOI：10.3762/bjoc.18.24

  日期：——

  the compounds showed practically no TcTS inhibition, whereas ca. 70% inhibition was observed for neuraminidase in relation to the analogues bearing hydrophobic substituents and ca. 5% for more polar substituents. These results suggest that polarity changes are less tolerated by neuraminidase due to the big difference in impact of hydrophobicity upon inhibition, thus indicating a simple approach to differentiate

  唾液酸是唾液酸酶的天然底物，其化学修饰是产生有效和选择性抑制剂的有用方法。为了推进选择性克氏锥虫反式唾液酸酶 (TcTS) 抑制剂的发现，我们通过铜催化的叠氮炔合成了一系列异头 1,2,3-三唑连接的唾液酸衍生物，收率高、纯度高环加成反应（CuAAC，点击化学）并评估了它们对 TcTS 和神经氨酸酶的活性。令人惊讶的是，这些化合物几乎没有表现出 TcTS 抑制作用，而约。与带有疏水取代基的类似物相比，观察到神经氨酸酶有 70% 的抑制作用。极性较大的取代基为 5%。这些结果表明，由于疏水性对抑制的影响存在巨大差异，神经氨酸酶对极性变化的耐受性较差，因此表明了区分这两种酶的简单方法。此外，这种选择性可能是基于位于 TcTS 活性位点上方的庞大疏水环引起的可能空间位阻，并可能阻止疏水抑制剂结合。本研究在利用唾液酸酶的细微结构差异方面向前迈出了一步，需要解决这些差异以实现选择性抑制。