N-[2-(2-hydroxyethoxy)ethyl]-9-oxofluorene-2-carboxamide | 1105063-60-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-[2-(2-hydroxyethoxy)ethyl]-9-oxofluorene-2-carboxamide
• CAS: 1105063-60-2
• 化学式: C₁₈H₁₇NO₄
• 分子量: 311.337
• InChiKey: WMQWWJIZTHPBRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[2-(2-hydroxyethoxy)ethyl]-9-oxofluorene-2-carboxamide 、 4-硝基苯-Β-D-吡喃葡萄糖苷 在 Aplysia fasciata β-glucosidase 作用下， 以 phosphate buffer 、 二甲基亚砜 为溶剂， 反应 2.5h， 以2.3%的产率得到9-oxo-N-[2-[2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethoxy]ethyl]fluorene-2-carboxamide
  参考文献：
  名称：

  2/4-Substituted-9-fluorenones and their O-glucosides as potential immunomodulators and anti-herpes simplex virus-2 agents. Part 5

  摘要：

  In pursuing a research on the antiviral and immunomodulatory activity of tilorone congeners, two new series of compounds were prepared and pharmacologically explored: 9-fluorenone carboxyhydroxyesters, indicated as AG, and 9-fluorenone carboxyhydroxamides, indicated as MG. Two of them, AG17 and MG3, were used as sugar acceptors in the transglycosylation reactions performed by alpha- and beta-glucosidases extracted from the marine mollusc Aplysia fasciata providing different alpha- and beta-, mono- and oligosaccharides. Then aglycons and saccharides were assayed for cytotoxicity, for anti-herpes virus-2 properties on peripheral blood monorruclear cells (PBMC) and for their capability to trigger human cells to produce antiviral cytokines such as IFN alpha and TNF alpha. Some promising compounds were individuated whereas the utility of the biocatalytic procedures in the preparation of pure anomeric material was further focused. (C) 2008 Elsevier Masson SAS. All fights reserved.

  DOI：

  10.1016/j.ejmech.2008.01.045
• 作为产物：
  描述：

  2-fluorenone-2-carbonyl chloride 、 二甘醇胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以48%的产率得到N-[2-(2-hydroxyethoxy)ethyl]-9-oxofluorene-2-carboxamide
  参考文献：
  名称：

  2/4-Substituted-9-fluorenones and their O-glucosides as potential immunomodulators and anti-herpes simplex virus-2 agents. Part 5

  摘要：

  In pursuing a research on the antiviral and immunomodulatory activity of tilorone congeners, two new series of compounds were prepared and pharmacologically explored: 9-fluorenone carboxyhydroxyesters, indicated as AG, and 9-fluorenone carboxyhydroxamides, indicated as MG. Two of them, AG17 and MG3, were used as sugar acceptors in the transglycosylation reactions performed by alpha- and beta-glucosidases extracted from the marine mollusc Aplysia fasciata providing different alpha- and beta-, mono- and oligosaccharides. Then aglycons and saccharides were assayed for cytotoxicity, for anti-herpes virus-2 properties on peripheral blood monorruclear cells (PBMC) and for their capability to trigger human cells to produce antiviral cytokines such as IFN alpha and TNF alpha. Some promising compounds were individuated whereas the utility of the biocatalytic procedures in the preparation of pure anomeric material was further focused. (C) 2008 Elsevier Masson SAS. All fights reserved.

  DOI：

  10.1016/j.ejmech.2008.01.045

文献信息

• 2/4-Substituted-9-fluorenones and their O-glucosides as potential immunomodulators and anti-herpes simplex virus-2 agents. Part 5
  作者：Adriana Arena、Nicoletta Arena、Rosella Ciurleo、Ambra de Gregorio、Rosanna Maccari、Rosaria Ottana'、Bernadette Pavone、Annabella Tramice、Antonio Trincone、Maria Gabriella Vigorita

  DOI：10.1016/j.ejmech.2008.01.045

  日期：2008.12

  In pursuing a research on the antiviral and immunomodulatory activity of tilorone congeners, two new series of compounds were prepared and pharmacologically explored: 9-fluorenone carboxyhydroxyesters, indicated as AG, and 9-fluorenone carboxyhydroxamides, indicated as MG. Two of them, AG17 and MG3, were used as sugar acceptors in the transglycosylation reactions performed by alpha- and beta-glucosidases extracted from the marine mollusc Aplysia fasciata providing different alpha- and beta-, mono- and oligosaccharides. Then aglycons and saccharides were assayed for cytotoxicity, for anti-herpes virus-2 properties on peripheral blood monorruclear cells (PBMC) and for their capability to trigger human cells to produce antiviral cytokines such as IFN alpha and TNF alpha. Some promising compounds were individuated whereas the utility of the biocatalytic procedures in the preparation of pure anomeric material was further focused. (C) 2008 Elsevier Masson SAS. All fights reserved.