N-benzyloxy-6-(4-dimethylaminobenzoylamino)capramide | 251304-84-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyloxy-6-(4-dimethylaminobenzoylamino)capramide
• 英文别名: 6-N-(4-dimethylaminophenylcarbamoyl)hexanoic acid N'-benzoyloxyamide；4-(dimethylamino)-N-[6-oxo-6-(phenylmethoxyamino)hexyl]benzamide
• CAS: 251304-84-4
• 化学式: C₂₂H₂₉N₃O₃
• 分子量: 383.491
• InChiKey: FOENILKCUMZMCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzyloxy-6-(4-dimethylaminobenzoylamino)capramide 在 10percent Pd/C 作用下， 以 甲醇 、 环己烷 为溶剂， 反应 6.0h， 以77%的产率得到CAY 10398
  参考文献：
  名称：

  An Easy and Convenient Synthesis of Weinreb Amides and Hydroxamates

  摘要：

  DOI：

  10.1021/jo015524b
• 作为产物：
  描述：

  叔丁氧羰酰基6-氨基己酸 在 N-甲基吗啉 、 三乙基硅烷 、 三氟乙酸 、 4-(4,6-二甲氧基三嗪-2-基)-4-甲基吗啉盐酸盐 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 21.5h， 生成 N-benzyloxy-6-(4-dimethylaminobenzoylamino)capramide
  参考文献：
  名称：

  An Easy and Convenient Synthesis of Weinreb Amides and Hydroxamates

  摘要：

  DOI：

  10.1021/jo015524b

文献信息

• 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.
• Amide Analogues of Trichostatin A as Inhibitors of Histone Deacetylase and Inducers of Terminal Cell Differentiation
  作者：Manfred Jung、Gerald Brosch、Doris Kölle、Hans Scherf、Clarissa Gerhäuser、Peter Loidl

  DOI：10.1021/jm991091h

  日期：1999.11.1

  Inhibitors of histone deacetylase (HD) bear great potential as new drugs due to their ability to modulate transcription and to induce apoptosis or differentiation in cancer cells. We have described previously analogues of the complex natural HD inhibitors trapoxin B and trichostatin A with activities in the submicromolar range. Here we report structure-activity relationship analyses of further analogues of trichostatin A with respect to in vitro inhibition of maize HD-2 and their ability to induce terminal cell differentiation in Friend leukemic cells. This is the first report that shows the correlation between HD inhibitory activity and action on cancer cells on a larger series of similar compounds. Only the compounds that inhibit HD induce differentiation and/or exert antiproliferative activities in cell culture. Our studies support the use of in vitro systems as screening tools and provide structure-activity relationships that merit further investigation of this interesting target.
• An Easy and Convenient Synthesis of Weinreb Amides and Hydroxamates
  作者：Lidia De Luca、Giampaolo Giacomelli、Maurizio Taddei

  DOI：10.1021/jo015524b

  日期：2001.4.1