14-[(2-Azidoethoxy)carbonyl]-1-(alpha-D-mannopyranosyloxy)-10,18-bis{[(4-{[2-(alpha-D-mannopyranosyloxy)ethyl]amino}-4-oxobutanoyl)oxy]methyl}-10,14,18-trimethyl-4,7,11,17-tetraoxo-8,12,16-trioxa-3-azanonadecan-19-yl 4-{[2-(alpha-D-mannopyranosyloxy)ethyl]amino}-4-oxobutanoate | 1207538-27-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 14-[(2-Azidoethoxy)carbonyl]-1-(alpha-D-mannopyranosyloxy)-10,18-bis{[(4-{[2-(alpha-D-mannopyranosyloxy)ethyl]amino}-4-oxobutanoyl)oxy]methyl}-10,14,18-trimethyl-4,7,11,17-tetraoxo-8,12,16-trioxa-3-azanonadecan-19-yl 4-{[2-(alpha-D-mannopyranosyloxy)ethyl]amino}-4-oxobutanoate
• 英文别名: [3-(2-azidoethoxy)-2-methyl-2-[[2-methyl-3-[4-oxo-4-[2-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethylamino]butanoyl]oxy-2-[[4-oxo-4-[2-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethylamino]butanoyl]oxymethyl]propanoyl]oxymethyl]-3-oxopropyl] 2-methyl-3-[4-oxo-4-[2-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethylamino]butanoyl]oxy-2-[[4-oxo-4-[2-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethylamino]butanoyl]oxymethyl]propanoate
• CAS: 1207538-27-9
• 化学式: C₆₅H₁₀₅N₇O₄₂
• 分子量: 1656.57
• InChiKey: WBVTXMCRHQSTAT-KFHXECOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -11
• 重原子数：
  114
• 可旋转键数：
  57
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  712
• 氢给体数：
  20
• 氢受体数：
  44

反应信息

• 作为产物：
  描述：

  、 2-aminoethyl α-D-mannopyranoside 在 N-[(dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylidene]-N-methylmethanaminium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 生成 14-[(2-Azidoethoxy)carbonyl]-1-(alpha-D-mannopyranosyloxy)-10,18-bis{[(4-{[2-(alpha-D-mannopyranosyloxy)ethyl]amino}-4-oxobutanoyl)oxy]methyl}-10,14,18-trimethyl-4,7,11,17-tetraoxo-8,12,16-trioxa-3-azanonadecan-19-yl 4-{[2-(alpha-D-mannopyranosyloxy)ethyl]amino}-4-oxobutanoate
  参考文献：
  名称：

  Inhibition of DC-SIGN-Mediated HIV Infection by a Linear Trimannoside Mimic in a Tetravalent Presentation

  摘要：

  HIV infection is pandemic in humans and is responsible for millions of deaths every year. The discovery of new cellular targets that can be used to prevent the infection process represents a new opportunity for developing more effective antiviral drugs. In this context, dendritic cell-specific ICAM-3 grabbing nonintegrin (DC-SIGN), a lectin expressed at the surface of immature dendritic cells and involved in the initial stages of HIV infection, is a promising therapeutic target. Herein we show the ability of a new tetravalent dendron containing four copies of a linear trimannoside mimic to inhibit the trans HIV infection process of CD4+ T lymphocytes at low micromolar range. This compound presents a high solubility in physiological media, a neglectable cytotoxicity, and a long-lasting effect and is based on carbohydrate-mimic units. Notably, the HIV antiviral activity is independent of viral tropism (X4 or R5). The formulation of this compound as a gel could allow its use as topical microbicide.

  DOI：

  10.1021/cb900216e