methyl 2-[3-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris[3-(2-methoxy-2-oxoethyl)sulfanylpropoxy]oxan-2-yl]methoxy]propylsulfanyl]acetate | 185564-71-0

• 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 2-[3-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris[3-(2-methoxy-2-oxoethyl)sulfanylpropoxy]oxan-2-yl]methoxy]propylsulfanyl]acetate
• CAS: 185564-71-0
• 化学式: C₃₁H₅₄O₁₄S₄
• 分子量: 779.025
• InChiKey: HKVYCCUPXPLIDX-DFYRYSMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  49
• 可旋转键数：
  34
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  262
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  methyl 2-[3-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris[3-(2-methoxy-2-oxoethyl)sulfanylpropoxy]oxan-2-yl]methoxy]propylsulfanyl]acetate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 以73%的产率得到methyl 2,3,4,6-tetra-O-(3-{[(sodium oxycarbonyl)methyl]thio}propyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Polyanion Inhibitors of Human Immunodeficiency Virus and Other Viruses. 6. Micelle-like Anti-HIV Polyanionic Compounds Based on a Carbohydrate Core

  摘要：

  A new class of polyanionic compounds, inhibitors of human immunodeficiency virus, was obtained from radical addition of mercapto acid or mercapto ester on a perallylated carbohydrate under UV irradiation with a catalytic amount of AIBN. Unlike the polyanions that we have previously prepared by polymerization reactions, the compounds are structurally well defined. Polyanions bearing 16 carboxylate groups showed a 50% inhibitory concentration (IC50) of 0.1-4.1 mu g/mL against HIV-1 in MT-4 cells while not being toxic to the host cells at concentrations up to 125 mu g/mL. The most potent polyanions also proved active against human cytomegalovirus at concentrations of 1-14 mu g/mL. No activity was observed against any of the other viruses tested (i.e., herpes simplex virus, vesicular stomatitis virus, Sindbis, Semliki forest, parainfluenza-3, Junin, Tacaribe, Coxsackie B4, polio-1, reo-1, or vaccinia virus).

  DOI：

  10.1021/jm960348y
• 作为产物：
  描述：

  alpha-甲基葡萄糖甙 在 偶氮二异丁腈 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 methyl 2-[3-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris[3-(2-methoxy-2-oxoethyl)sulfanylpropoxy]oxan-2-yl]methoxy]propylsulfanyl]acetate
  参考文献：
  名称：

  Polyanion Inhibitors of Human Immunodeficiency Virus and Other Viruses. 6. Micelle-like Anti-HIV Polyanionic Compounds Based on a Carbohydrate Core

  摘要：

  A new class of polyanionic compounds, inhibitors of human immunodeficiency virus, was obtained from radical addition of mercapto acid or mercapto ester on a perallylated carbohydrate under UV irradiation with a catalytic amount of AIBN. Unlike the polyanions that we have previously prepared by polymerization reactions, the compounds are structurally well defined. Polyanions bearing 16 carboxylate groups showed a 50% inhibitory concentration (IC50) of 0.1-4.1 mu g/mL against HIV-1 in MT-4 cells while not being toxic to the host cells at concentrations up to 125 mu g/mL. The most potent polyanions also proved active against human cytomegalovirus at concentrations of 1-14 mu g/mL. No activity was observed against any of the other viruses tested (i.e., herpes simplex virus, vesicular stomatitis virus, Sindbis, Semliki forest, parainfluenza-3, Junin, Tacaribe, Coxsackie B4, polio-1, reo-1, or vaccinia virus).

  DOI：

  10.1021/jm960348y

文献信息

• Polyanion Inhibitors of Human Immunodeficiency Virus and Other Viruses. 6. Micelle-like Anti-HIV Polyanionic Compounds Based on a Carbohydrate Core
  作者：Alain Leydet、Christine Jeantet-Segonds、Corinne Bouchitté、Céline Moullet、Bernard Boyer、Jean Pierre Roque、Myriam Witvrouw、José Este、Robert Snoeck、Graciela Andrei、Erik De Clercq

  DOI：10.1021/jm960348y

  日期：1997.1.1

  A new class of polyanionic compounds, inhibitors of human immunodeficiency virus, was obtained from radical addition of mercapto acid or mercapto ester on a perallylated carbohydrate under UV irradiation with a catalytic amount of AIBN. Unlike the polyanions that we have previously prepared by polymerization reactions, the compounds are structurally well defined. Polyanions bearing 16 carboxylate groups showed a 50% inhibitory concentration (IC50) of 0.1-4.1 mu g/mL against HIV-1 in MT-4 cells while not being toxic to the host cells at concentrations up to 125 mu g/mL. The most potent polyanions also proved active against human cytomegalovirus at concentrations of 1-14 mu g/mL. No activity was observed against any of the other viruses tested (i.e., herpes simplex virus, vesicular stomatitis virus, Sindbis, Semliki forest, parainfluenza-3, Junin, Tacaribe, Coxsackie B4, polio-1, reo-1, or vaccinia virus).