N-benzyloxy-N'-[1(S)-methoxycarbonyl-2-phenylethyl]suberoylbisamide | 251304-82-2

• 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: N-benzyloxy-N'-[1(S)-methoxycarbonyl-2-phenylethyl]suberoylbisamide
• 英文别名: methyl (2S)-2-[[8-oxo-8-(phenylmethoxyamino)octanoyl]amino]-3-phenylpropanoate
• CAS: 251304-82-2
• 化学式: C₂₅H₃₂N₂O₅
• 分子量: 440.539
• InChiKey: ACUAXAPFMDPNGZ-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  32
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-benzyloxy-N'-[1(S)-methoxycarbonyl-2-phenylethyl]suberoylbisamide 在 palladium on activated charcoal 盐酸 、 lithium hydroxide 、 氢气 作用下， 生成 (S)-2-(7-Hydroxycarbamoyl-heptanoylamino)-3-phenyl-propionic acid
  参考文献：
  名称：

  Analogues of trichosтatin a and trapoxin B as histone deacetylase inhibitors

  摘要：

  Inhibitors of histone deacetylase are potent inducers of differentiation and bear considerable potential as drugs for chemoprevention and treatment of cancer. So far only complex natural products and a few synthetic congeners have been identified as specific inhibitors. We have prepared a set of simple analogues in as little as four synthetic steps that have inhibitory potencies in the range of known cyclotetrapeptide inhibitors. These compounds are interesting leads for the design of potent inhibitors of histone deacetylase. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00284-9
• 作为产物：
  描述：

  辛二酸单甲酯 在 lithium hydroxide 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 N-benzyloxy-N'-[1(S)-methoxycarbonyl-2-phenylethyl]suberoylbisamide
  参考文献：
  名称：

  Inhibitors of Histone Deacetylase Suppress the Growth of MCF-7 Breast Cancer Cells

  摘要：

  Inhibitors of histone deacetylase are attracting increasing interest due to their influence on transcription, differentiation, and apoptosis. We have investigated two synthetic inhibitors 3 and 4 of histone deacetylase and the natural product inhibitor trichostatin A for their ability to suppress of MCF-7 breast cancer cells and here present complete and improved synthetic procedures. The compounds show a dose dependent inhibition of growth with the activities in the low micromolar and nanomolar range. Trichostatin shows cytocidal effects at 100 nM and still has activity comparable to cisplatin (0.5 mu M) at 10 nM. Whereas the synthetic inhibitor 3 has cytocidal activity at 10 mu M compound 4 shows a maximum of 40% growth suppression at that concentration.

  DOI：

  10.1002/(sici)1521-4184(199910)332:10<353::aid-ardp353>3.0.co;2-x

文献信息

• Analogues of trichosтatin a and trapoxin B as histone deacetylase inhibitors
  作者：Manfred Jung、Katharina Hoffmann、Gerald Brosch、Peter Loidl

  DOI：10.1016/s0960-894x(97)00284-9

  日期：1997.7

  Inhibitors of histone deacetylase are potent inducers of differentiation and bear considerable potential as drugs for chemoprevention and treatment of cancer. So far only complex natural products and a few synthetic congeners have been identified as specific inhibitors. We have prepared a set of simple analogues in as little as four synthetic steps that have inhibitory potencies in the range of known cyclotetrapeptide inhibitors. These compounds are interesting leads for the design of potent inhibitors of histone deacetylase. (C) 1997 Elsevier Science Ltd.
• Inhibitors of Histone Deacetylase Suppress the Growth of MCF-7 Breast Cancer Cells
  作者：Kathrin Schmidt、Ronald Gust、Manfred Jung

  DOI：10.1002/(sici)1521-4184(199910)332:10<353::aid-ardp353>3.0.co;2-x

  日期：1999.10

  Inhibitors of histone deacetylase are attracting increasing interest due to their influence on transcription, differentiation, and apoptosis. We have investigated two synthetic inhibitors 3 and 4 of histone deacetylase and the natural product inhibitor trichostatin A for their ability to suppress of MCF-7 breast cancer cells and here present complete and improved synthetic procedures. The compounds show a dose dependent inhibition of growth with the activities in the low micromolar and nanomolar range. Trichostatin shows cytocidal effects at 100 nM and still has activity comparable to cisplatin (0.5 mu M) at 10 nM. Whereas the synthetic inhibitor 3 has cytocidal activity at 10 mu M compound 4 shows a maximum of 40% growth suppression at that concentration.