5-acetamido-2,6-anhydro-4-(morpholin-4-yl)-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enoic acid | 1171908-91-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 5-acetamido-2,6-anhydro-4-(morpholin-4-yl)-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enoic acid
• 英文别名: 5-acetamido-2,6-anhydro-3,4,5-trideoxy-4-morpholino-D-glycero-D-galacto-non-2-enoate；5-acetamido-4-morpholin-4-yl-6-(1,2,3-trihydroxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid；(2R,3R,4S)-3-acetamido-4-morpholin-4-yl-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
• CAS: 1171908-91-0
• 化学式: C₁₅H₂₄N₂O₈
• 分子量: 360.364
• InChiKey: JPYOCDCYNVIACS-NRFQWKTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  149
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate 在 吡啶 、 水 、 potassium carbonate 、 三氟乙酸酐 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 12.5h， 生成 5-acetamido-2,6-anhydro-4-(morpholin-4-yl)-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enoic acid
  参考文献：
  名称：

  简单合成神经氨酸的N-全氟酰化和N-酰化的糖基，在4α位带有环状氨基取代基，可能是唾液酸酶的抑制剂†

  摘要：

  一种简单的合成N-全氟酰化和N-酰化糖基的方法神经氨酸，与仲环胺（吗啉 或者 哌啶）在4α位置已建立，从过乙酰化的N-乙酰神经氨酸甲酯开始，依次经历其直接N-酰化反应，然后进行C-4胺化，β消除和对N的选择性水解酯功能，而不会影响敏感的全氟酰胺。

  DOI：

  10.1039/c2ob07015d

文献信息

• Regio- and Stereocontrolled Palladium-Catalyzed Allylic Substitution on N-Acetylneuraminic Acid Derivatives
  作者：Chih-Wei Chang、Stéphanie Norsikian、Regis Guillot、Jean-Marie Beau

  DOI：10.1002/ejoc.200901452

  日期：2010.4

  stoichiometric preparation and study of the highly probable complexes involved in the catalytic reaction. Reactions of this type were also applied to other nucleophiles for the construction of C-C, C-N, and C-O bonds, leading to the major formation of the C-4 regioisomers. The selective transformation of some of the substitution products provided easy access to a variety of modified sialic acid derivatives

  已开发出一种高效的区域选择性和立体选择性钯催化烯丙基取代 N-乙酰神经氨酸 (Neu5Ac2en) 的 2,3-不饱和衍生物的方法。我们表明烯丙基化反应的效率取决于起始材料上合适的保护基团，并且丙二酸钠阴离子作为亲核试剂，区域选择性可以通过与钯配合物相关的配体的性质进行微调。这些结果可以通过化学计量制备和催化反应中涉及的极可能配合物的研究来解释。这种类型的反应也应用于其他亲核试剂以构建 CC、CN 和 CO 键，导致 C-4 区域异构体的主要形成。
• A simple synthesis of N-perfluoroacylated and N-acylated glycals of neuraminic acid with a cyclic aminic substituent at the 4α position as possible inhibitors of sialidases
  作者：Paola Rota、Pietro Allevi、Irene S. Agnolin、Roberto Mattina、Nadia Papini、Mario Anastasia

  DOI：10.1039/c2ob07015d

  日期：——

  (morpholine or piperidine) at the 4α position, has been set-up, starting from peracetylated N-acetylneuraminic acid methyl ester that undergoes, sequentially to its direct N-transacylation followed by a C-4 amination, a β-elimination, and a selective hydrolysis of the ester functions, without affecting the sensitive perfluorinated amide.

  一种简单的合成N-全氟酰化和N-酰化糖基的方法神经氨酸，与仲环胺（吗啉 或者 哌啶）在4α位置已建立，从过乙酰化的N-乙酰神经氨酸甲酯开始，依次经历其直接N-酰化反应，然后进行C-4胺化，β消除和对N的选择性水解酯功能，而不会影响敏感的全氟酰胺。
• Synthesis of C-4-modified zanamivir analogs as neuraminidase inhibitors and their anti-AIV activities
  作者：Deju Ye、Woo-Jin Shin、Ning Li、Wei Tang、Enguang Feng、Jian Li、Pei-Lan He、Jian-Ping Zuo、Hanjo Kim、Ky-Youb Nam、Weiliang Zhu、Baik-Lin Seong、Kyoung Tai No、Hualiang Jiang、Hong Liu

  DOI：10.1016/j.ejmech.2012.06.033

  日期：2012.8

  With the introduction of bioisosteres of the guanidinium group together with scaffold hopping, 35 zanamivir analogs with C-4-modification were synthesized, and their inhibitory activities against both group-1 and group-2 neuraminidase (H5N1 and H3N2) were determined. Compound 026 exerts the most potency, with IC50 values of 0.58 and 2.72 mu M against N2 and N1, respectively. Further preliminary anti-avian influenza virus (AIV, H5N1) activities against infected MDCK cells were evaluated, and D5 exerts similar to 58% protective against AIV infection, which was comparable to zanamivir (similar to 67%). In a rat pharmacokinetic study, compound D5 showed an increased plasma half-life (t(1/2)) compared to zanamivir following either intravenous or oral administration. This study may represent a new start point for the future development of improved anti-AIV agents. (C) 2012 Elsevier Masson SAS. All rights reserved.