dimethyl (1S,2S,4S,5S)-4-(((2R,3R,4S,5S,6S)-3,4,5-triacetoxy-6-(2-azidoethoxy)tetrahydro-2H-pyran-2-yl)methoxy)-5-(((2S,3S,4S,5R,6R)-3,4,5-tris(benzoyloxy)-6-((benzoyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)cyclohexane-1,2-dicarboxylate | 1207538-21-3

• 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: dimethyl (1S,2S,4S,5S)-4-(((2R,3R,4S,5S,6S)-3,4,5-triacetoxy-6-(2-azidoethoxy)tetrahydro-2H-pyran-2-yl)methoxy)-5-(((2S,3S,4S,5R,6R)-3,4,5-tris(benzoyloxy)-6-((benzoyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)cyclohexane-1,2-dicarboxylate
• CAS: 1207538-21-3
• 化学式: C₅₈H₆₁N₃O₂₃
• 分子量: 1168.13
• InChiKey: AAHJBBRQEUVBPK-ZVWBUZBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  84.0
• 可旋转键数：
  23.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  331.61
• 氢给体数：
  0.0
• 氢受体数：
  24.0

反应信息

• 作为反应物：
  描述：

  dimethyl (1S,2S,4S,5S)-4-(((2R,3R,4S,5S,6S)-3,4,5-triacetoxy-6-(2-azidoethoxy)tetrahydro-2H-pyran-2-yl)methoxy)-5-(((2S,3S,4S,5R,6R)-3,4,5-tris(benzoyloxy)-6-((benzoyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)cyclohexane-1,2-dicarboxylate 在 10% palladium on activated charcoal 甲醇 、 氢气 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.33h， 生成 dimethyl (1S,2S,4S,5S)-4-(((2R,3S,4S,5S,6S)-6-(2-aminoethoxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methoxy)-5-(((2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)cyclohexane-1,2-dicarboxylate
  参考文献：
  名称：

  Inhibitors of microbial infections

  摘要：

  本发明适用于医学领域，特别是涉及用于治疗和/或预防HIV，埃博拉，登革热，丙型肝炎，SARS或结核感染的新化合物。

  公开号：

  EP2289904A1
• 作为产物：
  描述：

  2-azidoethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 copper(II) bis(trifluoromethanesulfonate) 吡啶 、 甲醇 、 四丁基氟化铵 、 sodium methylate 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.66h， 生成 dimethyl (1S,2S,4S,5S)-4-(((2R,3R,4S,5S,6S)-3,4,5-triacetoxy-6-(2-azidoethoxy)tetrahydro-2H-pyran-2-yl)methoxy)-5-(((2S,3S,4S,5R,6R)-3,4,5-tris(benzoyloxy)-6-((benzoyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)cyclohexane-1,2-dicarboxylate
  参考文献：
  名称：

  Inhibitors of microbial infections

  摘要：

  本发明适用于医学领域，特别是涉及用于治疗和/或预防HIV，埃博拉，登革热，丙型肝炎，SARS或结核感染的新化合物。

  公开号：

  EP2289904A1

文献信息

• [EN] INHIBITORS OF MICROBIAL INFECTIONS<br/>[FR] INHIBITEURS D'INFECTIONS MICROBIENNES
  申请人：UNIV DEGLI STUDI MILANO

  公开号：WO2011000721A1

  公开（公告）日：2011-01-06

  The present invention finds application in the field of medicine and, in particular, it relates to new compounds for the treatment and/or prevention of HIV; Ebola, Dengue, Hepatitis C, SARS or tuberculosis infections.

  本发明适用于医学领域，特别是涉及用于治疗和/或预防HIV、埃博拉、登革热、丙型肝炎、SARS或结核感染的新化合物。
• Inhibition of DC-SIGN-Mediated HIV Infection by a Linear Trimannoside Mimic in a Tetravalent Presentation
  作者：Sara Sattin、Anna Daghetti、Michel Thépaut、Angela Berzi、Macarena Sánchez-Navarro、Georges Tabarani、Javier Rojo、Franck Fieschi、Mario Clerici、Anna Bernardi

  DOI：10.1021/cb900216e

  日期：2010.3.19

  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.