(4S,4aR,5S,5aR,6R,12aS)-4-(dimethylamino)-9-(N-methoxyglycyl)amino-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 四环素类
• 英文名称: (4S,4aR,5S,5aR,6R,12aS)-4-(dimethylamino)-9-(N-methoxyglycyl)amino-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
• 化学式: C₂₅H₃₀N₄O₁₀
• 分子量: 546.534
• InChiKey: BJYZLQVUQXVZRN-XPEKFKQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.26
• 重原子数：
  39.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  231.98
• 氢给体数：
  8.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (4S,4aR,5S,5aR,6R,12aS)-4-(dimethylamino)-9-(N-methoxyglycyl)amino-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide 在 Pd/CaSO₄ 、 氢气 、 三氟乙酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 (4S,4aR,5S,5aR,6R,12aS)-4-(dimethylamino)-9-(N-methoxy-N-6'-deoxy-6'-amino-β-D-glucopyranosylglycyl)amino-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of Doxycycline Neoglycosides

  摘要：

  A set of 37 doxycycline neoglycosides were prepared, mediated via a C-9 alkoxyamino-glycyl-based spacer reminiscent of that of tigecycline. Subsequent in vitro antibacterial assays against representative drug-resistant Gram negative and Gram positive strains revealed a sugar-dependent activity profile and one doxycycline neoglycoside, the 2'-amino-alpha-D-glucoside conjugate, to rival that of the parent pharmacophore. In contrast, the representative tetracycline-susceptible strain E. coli 25922 was found to be relatively responsive to a range of doxycycline neoglycosides. This study also extends the use of aminosugars in the context of neoglycosylation via a simple two-step strategy anticipated to be broadly applicable for neoglycorandomization.

  DOI：

  10.1021/np4003096
• 作为产物：
  描述：

  <4S-(4α,12aα)>-4-(dimethylamino)-9-nitro-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide 在 吡啶 、 盐酸 、 Pd/CaSO₄ 、 氢气 、 trimethylamine borane 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 (4S,4aR,5S,5aR,6R,12aS)-4-(dimethylamino)-9-(N-methoxyglycyl)amino-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of Doxycycline Neoglycosides

  摘要：

  A set of 37 doxycycline neoglycosides were prepared, mediated via a C-9 alkoxyamino-glycyl-based spacer reminiscent of that of tigecycline. Subsequent in vitro antibacterial assays against representative drug-resistant Gram negative and Gram positive strains revealed a sugar-dependent activity profile and one doxycycline neoglycoside, the 2'-amino-alpha-D-glucoside conjugate, to rival that of the parent pharmacophore. In contrast, the representative tetracycline-susceptible strain E. coli 25922 was found to be relatively responsive to a range of doxycycline neoglycosides. This study also extends the use of aminosugars in the context of neoglycosylation via a simple two-step strategy anticipated to be broadly applicable for neoglycorandomization.

  DOI：

  10.1021/np4003096

文献信息

• Synthesis and Antibacterial Activity of Doxycycline Neoglycosides
  作者：Jianjun Zhang、Larissa V. Ponomareva、Karen Marchillo、Maoquan Zhou、David R. Andes、Jon S. Thorson

  DOI：10.1021/np4003096

  日期：2013.9.27

  A set of 37 doxycycline neoglycosides were prepared, mediated via a C-9 alkoxyamino-glycyl-based spacer reminiscent of that of tigecycline. Subsequent in vitro antibacterial assays against representative drug-resistant Gram negative and Gram positive strains revealed a sugar-dependent activity profile and one doxycycline neoglycoside, the 2'-amino-alpha-D-glucoside conjugate, to rival that of the parent pharmacophore. In contrast, the representative tetracycline-susceptible strain E. coli 25922 was found to be relatively responsive to a range of doxycycline neoglycosides. This study also extends the use of aminosugars in the context of neoglycosylation via a simple two-step strategy anticipated to be broadly applicable for neoglycorandomization.