5-acetamido-2,6-anhydro-3,5-dideoxy-4-[2-p-tolyl-N'-(methylsulfonyl)acetimidamido]-D-glycero-D-galacto-non-2-enonic acid | 1304780-18-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-acetamido-2,6-anhydro-3,5-dideoxy-4-[2-p-tolyl-N'-(methylsulfonyl)acetimidamido]-D-glycero-D-galacto-non-2-enonic acid
• 英文别名: (2R,3R,4S)-3-acetamido-4-[[2-(4-fluorophenyl)-1-(methanesulfonamido)ethylidene]amino]-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
• CAS: 1304780-18-4
• 化学式: C₂₀H₂₆FN₃O₉S
• 分子量: 503.506
• InChiKey: XPJCJXNZQLNTMG-RMIBSVFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  203
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  N-acetyl neuraminic acid 在 吡啶 、 甲醇 、 copper(l) iodide 、 三氟甲磺酸三甲基硅酯 、 叠氮基三甲基硅烷 、 氢气 、 sodium methylate 、 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 氯仿 、 水 、 乙酸乙酯 、 叔丁醇 为溶剂， 反应 23.5h， 生成 5-acetamido-2,6-anhydro-3,5-dideoxy-4-[2-p-tolyl-N'-(methylsulfonyl)acetimidamido]-D-glycero-D-galacto-non-2-enonic acid
  参考文献：
  名称：

  Syntheses of 2-deoxy-2,3-didehydro-N-acetylneuraminic acid analogues modified by N-sulfonylamidino groups at the C-4 position and biological evaluation as inhibitors of human parainfluenza virus type 1

  摘要：

  Eleven novel sialidase inhibitors 9 and 10 with an N-sulfonylamidino group at the C-4 position of Neu 5Ac2en 1 against human parainfluenza virus type 1 (hPIV-1) were synthesized using copper-catalyzed three-component coupling reactions, and their inhibitory activities against hPIV-1 sialidase were studied. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.010

文献信息

• Syntheses of 2-deoxy-2,3-didehydro-N-acetylneuraminic acid analogues modified by N-sulfonylamidino groups at the C-4 position and biological evaluation as inhibitors of human parainfluenza virus type 1
  作者：Reiko Nishino、Kiyoshi Ikeda、Takuya Hayakawa、Tadanobu Takahashi、Takashi Suzuki、Masayuki Sato

  DOI：10.1016/j.bmc.2011.02.010

  日期：2011.4

  Eleven novel sialidase inhibitors 9 and 10 with an N-sulfonylamidino group at the C-4 position of Neu 5Ac2en 1 against human parainfluenza virus type 1 (hPIV-1) were synthesized using copper-catalyzed three-component coupling reactions, and their inhibitory activities against hPIV-1 sialidase were studied. (C) 2011 Elsevier Ltd. All rights reserved.