methyl (1-(pent-3-yl) 2-acetamido-3-O-acetyl-2,4-dideoxy-α-L-threo-hex-4-enopyranosid)uronate | 223423-12-9

• 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 (1-(pent-3-yl) 2-acetamido-3-O-acetyl-2,4-dideoxy-α-L-threo-hex-4-enopyranosid)uronate
• 英文别名: methyl (2R,3R,4S)-3-acetamido-4-acetyloxy-2-pentan-3-yloxy-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 223423-12-9
• 化学式: C₁₆H₂₅NO₇
• 分子量: 343.377
• InChiKey: VGGHXWILQUFFLF-JGGQBBKZSA-N

物化性质

• 沸点：
  480.5±45.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (1-(pent-3-yl) 2-acetamido-3-O-acetyl-2,4-dideoxy-α-L-threo-hex-4-enopyranosid)uronate 在 甲醇 、 sodium methylate 、 四丁基碘化铵 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 24.5h， 生成 methyl (1-(pent-3-yl) 2-acetamido-2,4-dideoxy-3-O-methyl-α-L-threo-hex-4-enopyranosid)uronate
  参考文献：
  名称：

  Exploring the Interactions of Unsaturated Glucuronides with Influenza Virus Sialidase

  摘要：

  A series of C3 O-functionalized 2-acetamido-2-deoxy-Delta(4)-beta-D-glucuronides were synthesized to explore noncharge interactions in subsite 2 of the influenza virus sialidase active site. In complex with A/N8 sialidase, the parent compound (C3 OH) inverts its solution conformation to bind with all substituents well positioned in the active site. The parent compound inhibits influenza virus sialidase at a sub-mu M level; the introduction of small alkyl substituents or an acetyl group at C3 is also tolerated.

  DOI：

  10.1021/jm301145k
• 作为产物：
  描述：

  在 4-二甲氨基吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 生成 methyl (1-(pent-3-yl) 2-acetamido-3-O-acetyl-2,4-dideoxy-α-L-threo-hex-4-enopyranosid)uronate
  参考文献：
  名称：

  Exploring the Interactions of Unsaturated Glucuronides with Influenza Virus Sialidase

  摘要：

  A series of C3 O-functionalized 2-acetamido-2-deoxy-Delta(4)-beta-D-glucuronides were synthesized to explore noncharge interactions in subsite 2 of the influenza virus sialidase active site. In complex with A/N8 sialidase, the parent compound (C3 OH) inverts its solution conformation to bind with all substituents well positioned in the active site. The parent compound inhibits influenza virus sialidase at a sub-mu M level; the introduction of small alkyl substituents or an acetyl group at C3 is also tolerated.

  DOI：

  10.1021/jm301145k

文献信息

• Sialidase inhibitors related to zanamivir: Synthesis and biological evaluation of 4H-pyran 6-ether and ketone
  作者：Paul W. Smith、J.Ed Robinson、Derek N. Evans、Steven L. Sollis、Peter D. Howes、Naimisha Trivedi、Richard C. Bethell

  DOI：10.1016/s0960-894x(99)00031-1

  日期：1999.2

  Synthesis of 5R-Acetamido-4S-amino-4H-pyran-6R-O-( -ethyl)propyl and 6R-(1-oxo-2-ethyl)butyl 2-carboxylic acids (4 and 5) and their evaluation as inhibitors of influenza virus sialidase is described. Both compounds showed good inhibitory activity with marked selectivity for influenza A sialidase.

  5R-乙酰氨基-4S-氨基-4H-吡喃-6R-O-（-乙基）丙基和6R-（1-氧代-2-乙基）丁基2-羧酸（4和5）的合成及其作为抑制剂的评估描述了流感病毒唾液酸酶的分离。两种化合物均显示出良好的抑制活性，并对甲型流感病毒唾液酸酶具有明显的选择性。