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N-{4-[2-(3,5-Dihydroxyphenyl)ethenyl]phenyl}acetamide | 823804-72-4

中文名称
——
中文别名
——
英文名称
N-{4-[2-(3,5-Dihydroxyphenyl)ethenyl]phenyl}acetamide
英文别名
N-[4-[2-(3,5-dihydroxyphenyl)ethenyl]phenyl]acetamide
N-{4-[2-(3,5-Dihydroxyphenyl)ethenyl]phenyl}acetamide化学式
CAS
823804-72-4
化学式
C16H15NO3
mdl
——
分子量
269.3
InChiKey
VDFSSDUOSSQJAG-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    2.7
  • 重原子数:
    20
  • 可旋转键数:
    3
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.06
  • 拓扑面积:
    69.6
  • 氢给体数:
    3
  • 氢受体数:
    3

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为产物:
    参考文献:
    名称:
    Novel resveratrol derivatives have diverse effects on the survival, proliferation and senescence of primary human fibroblasts
    摘要:
    Resveratrol alters the cytokinetics of mammalian cell populations in a dose dependent manner. Concentrations above 25-50 mu M typically trigger growth arrest, senescence and/or apoptosis in multiple different cell types. In contrast, concentrations below 10 mu M enhance the growth of log phase cell cultures and can rescue senescence in multiple strains of human fibroblasts. To better understand the structural features that regulate these effects, a panel of 24 structurally-related resveralogues were synthesised and evaluated for their capacity to activate SIRT1, as determined by an ex-vivo SIRT1 assay, their toxicity, as measured by lactate dehydrogenase release, and their effects on replicative senescence in MRC5 human fibroblasts as measured by their effects on Ki67 immunoreactivity and senescence-associated beta galactosidase activity. Minor modifications to the parent stilbene, resveratrol, significantly alter the biological activities of the molecules. Replacement of the 3,5-dihydroxy substituents with 3,5-dimethoxy groups significantly enhances SIRT1 activity, and reduces toxicity. Minimising other strong conjugative effects also reduces toxicity, but negatively impacts SIRT1 activation. At 100 mu M many of the compounds, including resveratrol, induce senescence in primary MRC5 cells in culture. Modifications that reduce or remove this effect match those that reduce toxicity leading to a correlation between reduction in labelling index and increase in LDH release. At 10 mu M, the majority of our compounds significantly enhance the growth fraction of log phase cultures of MRC5 cells, consistent with the rescue of a subpopulation of cells within the culture from senescence. SIRT1 activation is not required for rescue to occur but enhances the size of the effect.
    DOI:
    10.1007/s10522-020-09896-6
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文献信息

  • Novel resveratrol derivatives have diverse effects on the survival, proliferation and senescence of primary human fibroblasts
    作者:Vishal C. Birar、Angela N. Sheerin、Elizabeth L. Ostler、Richard G. A. Faragher
    DOI:10.1007/s10522-020-09896-6
    日期:2020.12
    Resveratrol alters the cytokinetics of mammalian cell populations in a dose dependent manner. Concentrations above 25-50 mu M typically trigger growth arrest, senescence and/or apoptosis in multiple different cell types. In contrast, concentrations below 10 mu M enhance the growth of log phase cell cultures and can rescue senescence in multiple strains of human fibroblasts. To better understand the structural features that regulate these effects, a panel of 24 structurally-related resveralogues were synthesised and evaluated for their capacity to activate SIRT1, as determined by an ex-vivo SIRT1 assay, their toxicity, as measured by lactate dehydrogenase release, and their effects on replicative senescence in MRC5 human fibroblasts as measured by their effects on Ki67 immunoreactivity and senescence-associated beta galactosidase activity. Minor modifications to the parent stilbene, resveratrol, significantly alter the biological activities of the molecules. Replacement of the 3,5-dihydroxy substituents with 3,5-dimethoxy groups significantly enhances SIRT1 activity, and reduces toxicity. Minimising other strong conjugative effects also reduces toxicity, but negatively impacts SIRT1 activation. At 100 mu M many of the compounds, including resveratrol, induce senescence in primary MRC5 cells in culture. Modifications that reduce or remove this effect match those that reduce toxicity leading to a correlation between reduction in labelling index and increase in LDH release. At 10 mu M, the majority of our compounds significantly enhance the growth fraction of log phase cultures of MRC5 cells, consistent with the rescue of a subpopulation of cells within the culture from senescence. SIRT1 activation is not required for rescue to occur but enhances the size of the effect.
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