methyl (2R,3R,4S)-3-(2-azidoacetamido)-4-hydroxy-2-((1R,2R)-1,2,3-trihydroxypropyl)-3,4-dihydro-2H-pyran-6-carboxylate | 1261081-34-8

• 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: methyl (2R,3R,4S)-3-(2-azidoacetamido)-4-hydroxy-2-((1R,2R)-1,2,3-trihydroxypropyl)-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 1261081-34-8
• 化学式: C₁₂H₁₈N₄O₈
• 分子量: 346.297
• InChiKey: IIGSQISSFVBVQL-FAMUSVHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.69
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  194.31
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  苯基炔丙基醚 、 methyl (2R,3R,4S)-3-(2-azidoacetamido)-4-hydroxy-2-((1R,2R)-1,2,3-trihydroxypropyl)-3,4-dihydro-2H-pyran-6-carboxylate 在 copper(II) sulfate 、 sodium ascorbate 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 、 正丁醇 为溶剂， 生成 (2R,3R,4S)-4-hydroxy-3-(2-(4-(phenoxymethyl)-1H-1,2,3-triazol-1-yl)acetamido)-2-((1R,2R)-1,2,3-trihydroxypropyl)-3,4-dihydro-2H-pyran-6-carboxylate
  参考文献：
  名称：

  Inhibition of human neuraminidase 3 (NEU3) by C9-triazole derivatives of 2,3-didehydro-N-acetyl-neuraminic acid

  摘要：

  We report the synthesis of a series of C9 and N5Ac modified analogs of 2,3-didehydro-N-acetyl-neuraminic acid (DANA) and their inhibitory potency for the human neuraminidase 3 (NEU3) enzyme. We were able to generate a small library of compounds through the synthesis of azide derivatives of DANA, followed by Cu-catalyzed azide-alkyne cycloaddition (CuAAC) to generate triazole-containing inhibitors. Our results suggest that NEU3 can tolerate large hydrophobic groups at the C9 position; however, none of the derivatives made at the N5Ac side-chain were active. We identify three new inhibitors that have comparable potency to the best reported inhibitors of the enzyme. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.111
• 作为产物：
  描述：

  (1S,2R)-1-((2R,3R,4S)-4-acetoxy-3-(2-azidoacetamido)-6-(methoxycarbonyl)-3,4-dihydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate 在 甲醇 、 sodium methylate 作用下， 反应 1.0h， 以52%的产率得到methyl (2R,3R,4S)-3-(2-azidoacetamido)-4-hydroxy-2-((1R,2R)-1,2,3-trihydroxypropyl)-3,4-dihydro-2H-pyran-6-carboxylate
  参考文献：
  名称：

  Inhibition of human neuraminidase 3 (NEU3) by C9-triazole derivatives of 2,3-didehydro-N-acetyl-neuraminic acid

  摘要：

  We report the synthesis of a series of C9 and N5Ac modified analogs of 2,3-didehydro-N-acetyl-neuraminic acid (DANA) and their inhibitory potency for the human neuraminidase 3 (NEU3) enzyme. We were able to generate a small library of compounds through the synthesis of azide derivatives of DANA, followed by Cu-catalyzed azide-alkyne cycloaddition (CuAAC) to generate triazole-containing inhibitors. Our results suggest that NEU3 can tolerate large hydrophobic groups at the C9 position; however, none of the derivatives made at the N5Ac side-chain were active. We identify three new inhibitors that have comparable potency to the best reported inhibitors of the enzyme. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.111