(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 | 1261081-43-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (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
• 英文别名: (2R,3R,4S)-4-hydroxy-3-[[2-[4-(phenoxymethyl)triazol-1-yl]acetyl]amino]-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
• CAS: 1261081-43-9
• 化学式: C₂₀H₂₄N₄O₉
• 分子量: 464.432
• InChiKey: WZTJFGOYDVBWTQ-RMIBSVFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  197
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  (2R,3R,4S)-3-[(tert-Butoxycarbonyl)amino]-4-hydroxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid 在 吡啶 、 甲醇 、 sodium methylate 、 copper(II) sulfate 、 sodium ascorbate 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 正丁醇 为溶剂， 反应 17.5h， 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

文献信息

• Inhibition of human neuraminidase 3 (NEU3) by C9-triazole derivatives of 2,3-didehydro-N-acetyl-neuraminic acid
  作者：Yao Zou、Amgad Albohy、Mahendra Sandbhor、Christopher W. Cairo

  DOI：10.1016/j.bmcl.2010.09.111

  日期：2010.12

  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.