3-[2-(3,4-dimethoxyphenyl)ethyl]-3,4-dihydro-1-(3-hydroxy-4-methoxyphenyl)-8-methoxy-4-oxo-[1]benzopyrano[3,4-b]pyrrol-7-yl 2,2,2-trichloroethyl sulfate | 1352336-49-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-[2-(3,4-dimethoxyphenyl)ethyl]-3,4-dihydro-1-(3-hydroxy-4-methoxyphenyl)-8-methoxy-4-oxo-[1]benzopyrano[3,4-b]pyrrol-7-yl 2,2,2-trichloroethyl sulfate
• CAS: 1352336-49-2
• 化学式: C₃₁H₂₈Cl₃NO₁₁S
• 分子量: 728.988
• InChiKey: ZTVZGZBLNLTXCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.41
• 重原子数：
  47.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  144.89
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  3-[2-(3,4-dimethoxyphenyl)ethyl]-3,4-dihydro-1-(3-hydroxy-4-methoxyphenyl)-8-methoxy-4-oxo-[1]benzopyrano[3,4-b]pyrrol-7-yl 2,2,2-trichloroethyl sulfate 在 甲酸铵 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 15.0h， 以90%的产率得到sodium 3-[2-(3,4-dimethoxyphenyl)ethyl]-3,4-dihydro-1-(3-hydroxy-4-methoxyphenyl)-8-methoxy-4-oxo-[1]benzopyrano[3,4-b]pyrrol-7-yl sulfate
  参考文献：
  名称：

  Synthesis, structure–activity relationships, and mechanism of action of anti-HIV-1 lamellarin α 20-sulfate analogues

  摘要：

  Lamellarin a and six different types of lamellarin alpha 20-sulfate analogues were synthesized and their structure-activity relationships were investigated using a single round HIV-1 vector infection assay. All lamellarin sulfates having pentacyclic lamellarin core exhibited anti-HIV-1 activity at a 10 mu M concentration range regardless of the number and position of the sulfate group. On the other hand, non-sulfated lamellarin alpha and ring-opened lamellarin sulfate analogues did not affect HIV-1 vector infection in similar concentrations. The lamellarin sulfates utilized in this study did not exhibit unfavorable cytotoxic effect under the concentrations tested (IC50 > 100 mu M). Confocal laser scanning microscopic analysis indicated that hydrophilic lamellarin sulfates were hardly incorporated in the cell. HIV-1 Env-mediated cell-cell fusion was suppressed by lamellarin sulfates. These results suggested that lamellarin sulfates have a novel anti-HIV-1 activity besides the previously reported integrase activity inhibition, possibly at a viral entry step of HIV-1 replication. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.030
• 作为产物：
  描述：

  在 喹啉 、 盐酸 、 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氢气 、 4-甲基苯磺酸吡啶 、 三乙胺 、 copper(II) oxide 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 49.17h， 生成 3-[2-(3,4-dimethoxyphenyl)ethyl]-3,4-dihydro-1-(3-hydroxy-4-methoxyphenyl)-8-methoxy-4-oxo-[1]benzopyrano[3,4-b]pyrrol-7-yl 2,2,2-trichloroethyl sulfate
  参考文献：
  名称：

  Synthesis, structure–activity relationships, and mechanism of action of anti-HIV-1 lamellarin α 20-sulfate analogues

  摘要：

  Lamellarin a and six different types of lamellarin alpha 20-sulfate analogues were synthesized and their structure-activity relationships were investigated using a single round HIV-1 vector infection assay. All lamellarin sulfates having pentacyclic lamellarin core exhibited anti-HIV-1 activity at a 10 mu M concentration range regardless of the number and position of the sulfate group. On the other hand, non-sulfated lamellarin alpha and ring-opened lamellarin sulfate analogues did not affect HIV-1 vector infection in similar concentrations. The lamellarin sulfates utilized in this study did not exhibit unfavorable cytotoxic effect under the concentrations tested (IC50 > 100 mu M). Confocal laser scanning microscopic analysis indicated that hydrophilic lamellarin sulfates were hardly incorporated in the cell. HIV-1 Env-mediated cell-cell fusion was suppressed by lamellarin sulfates. These results suggested that lamellarin sulfates have a novel anti-HIV-1 activity besides the previously reported integrase activity inhibition, possibly at a viral entry step of HIV-1 replication. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.030