β-[3-(9-oxo-9H-fluorenecarbonyloxy)propyl] glucoside

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: β-[3-(9-oxo-9H-fluorenecarbonyloxy)propyl] glucoside
• 英文别名: 3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl 9-oxofluorene-2-carboxylate
• 化学式: C₂₃H₂₄O₉
• 分子量: 444.438
• InChiKey: WMCNYBAMCPVZFR-OXUVVOBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  143
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  9-芴酮-2-羧酸 在 acetate buffer 、 Sulfolobus solfataricus β-glycosidase 、 硫酸 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 β-[3-(9-oxo-9H-fluorenecarbonyloxy)propyl] glucoside
  参考文献：
  名称：

  Biocatalysed synthesis of β-O-glucosides from 9-fluorenon-2-carbohydroxyesters. Part 3: IFN-inducing and anti-HSV-2 properties

  摘要：

  In pursuing research on the antiviral, interferon (IFN)-inducing tilorone congeners, a new series of fluoren-carboxyhydroxyesters has been prepared and biologically explored. These esters have subsequently been used as sugar acceptors in the enzymatic transglycosylation reaction using the 'retaining' P-glycosidase from the archaeon Sulfolobus solfataricus (Ss beta-Gly).Both aglycones (1-6) and corresponding beta-glucosides (beta-glu 1-beta-glu 6) have been screened for cytotoxicity, interferon-stimulating and antiviral properties against HSV-2.It was found that the addition of compounds beta-glu 5, beta-glu 6 and beta-glu 4 to HSV-2 infected U937 cells downregulates viral replication and triggers cells to release IFN-alpha/beta. Taken together, the results showed improved pharmacological profiles as a consequence of glycosylation. A molecular modelling study carried out on this series of compounds completed the structural characterisation of the novel compounds. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.016

文献信息

• Biocatalysed synthesis of β-O-glucosides from 9-fluorenon-2-carbohydroxyesters. Part 3: IFN-inducing and anti-HSV-2 properties
  作者：Stefano Alcaro、Adriana Arena、Rosaria Di Bella、Simonetta Neri、Rosaria Ottanà、Francesco Ortuso、Bernadette Pavone、Antonio Trincone、Maria Gabriella Vigorita

  DOI：10.1016/j.bmc.2005.03.016

  日期：2005.5

  In pursuing research on the antiviral, interferon (IFN)-inducing tilorone congeners, a new series of fluoren-carboxyhydroxyesters has been prepared and biologically explored. These esters have subsequently been used as sugar acceptors in the enzymatic transglycosylation reaction using the 'retaining' P-glycosidase from the archaeon Sulfolobus solfataricus (Ss beta-Gly).Both aglycones (1-6) and corresponding beta-glucosides (beta-glu 1-beta-glu 6) have been screened for cytotoxicity, interferon-stimulating and antiviral properties against HSV-2.It was found that the addition of compounds beta-glu 5, beta-glu 6 and beta-glu 4 to HSV-2 infected U937 cells downregulates viral replication and triggers cells to release IFN-alpha/beta. Taken together, the results showed improved pharmacological profiles as a consequence of glycosylation. A molecular modelling study carried out on this series of compounds completed the structural characterisation of the novel compounds. (c) 2005 Elsevier Ltd. All rights reserved.