methyl 5-acetamido-2,6-anhydro-4-azido-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-galacto-non-2-enonate | 1449035-93-1

• 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: methyl 5-acetamido-2,6-anhydro-4-azido-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-galacto-non-2-enonate
• CAS: 1449035-93-1
• 化学式: C₂₂H₂₈N₄O₇
• 分子量: 460.487
• InChiKey: YJMCYXHCGNDVFD-TWHPPBISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.12
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  174.08
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 5-acetamido-2,6-anhydro-4-azido-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-galacto-non-2-enonate 在 硫化氢 作用下， 以 吡啶 为溶剂， 反应 16.0h， 以80%的产率得到methyl 5-acetamido-2,6-anhydro-4-amino-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-galacto-non-2-enonate
  参考文献：
  名称：

  Novel 3,4-disubstituted-Neu5Ac2en derivatives as probes to investigate flexibility of the influenza virus sialidase 150-loop

  摘要：

  Novel 3,4-disubstituted-Neu5Ac2en derivatives have been synthesised to probe the open 150-loop conformation of influenza virus sialidases. Both equatorially and axially (epi) substituted C4 amino and guanidino 3-(p-tolyl)allyl-Neu5Ac2en derivatives were prepared, via the 4-epi-hydroxy derivative. The equatorially-substituted 4-amino derivative showed low micromolar inhibition of both group-1 (pdm09 H1N1) and group-2 (pdm57 H2N2) sialidases, and provides the first in vitro evidence that a group-2 sialidase may exhibit 150-loop flexibility. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.054
• 作为产物：
  描述：

  3-(p-tolyl)allyl-Neu5Ac2en 4,5-oxazoline 在 二苯基膦叠氮化物 、 水 、 sodium methylate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 甲醇 、 乙酸乙酯 、 苯 为溶剂， 反应 24.25h， 生成 methyl 5-acetamido-2,6-anhydro-4-azido-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-galacto-non-2-enonate
  参考文献：
  名称：

  Novel 3,4-disubstituted-Neu5Ac2en derivatives as probes to investigate flexibility of the influenza virus sialidase 150-loop

  摘要：

  Novel 3,4-disubstituted-Neu5Ac2en derivatives have been synthesised to probe the open 150-loop conformation of influenza virus sialidases. Both equatorially and axially (epi) substituted C4 amino and guanidino 3-(p-tolyl)allyl-Neu5Ac2en derivatives were prepared, via the 4-epi-hydroxy derivative. The equatorially-substituted 4-amino derivative showed low micromolar inhibition of both group-1 (pdm09 H1N1) and group-2 (pdm57 H2N2) sialidases, and provides the first in vitro evidence that a group-2 sialidase may exhibit 150-loop flexibility. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.054