N-(4-chlorophenyl)-N'-hydroxyoctanediamide | 1219807-83-6

• 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-(4-chlorophenyl)-N'-hydroxyoctanediamide
• CAS: 1219807-83-6
• 化学式: C₁₄H₁₉ClN₂O₃
• 分子量: 298.769
• InChiKey: PMJKWBOBDMWJSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  Methyl 8-(4-chloroanilino)-8-oxooctanoate 在 羟胺 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 N-(4-chlorophenyl)-N'-hydroxyoctanediamide
  参考文献：
  名称：

  Precursor-Directed Biosynthesis of Aminofulvenes: New Chalanilines from Endophytic Fungus Chalara sp.

  摘要：

  植物内生真菌 Chalara sp. 能够将表观遗传修饰剂 vorinostat 生物转化为形成独特的含苯胺的聚酮类化合物，被命名为 chalanilines。在这里，我们试图通过改变前体 vorinostat 中的苯胺基团来扩展 chalaniline A 类分子的化学多样性。总共，通过两步合成制备了二十三种不同的 vorinostat 类似物，其中十九种被真菌转化为聚酮类化合物。选择产量最高的底物进行大规模前体导向生物合成，分离、纯化并结构表征了五种新化合物，包括两种氟代 chalanilines。结构阐明依赖于一维和二维核磁共振技术，并得到低分辨率和高分辨率质谱的支持。所有化合物均进行了生物活性测试，但在抗微生物或细胞存活率测定中均不活跃。含氨基富烯的天然产物很少见，而这种高产率的前体导向过程允许对这类化合物进行多样化。

  DOI：

  10.3390/molecules26154418

文献信息

• Modified Cap Group Suberoylanilide Hydroxamic Acid Histone Deacetylase Inhibitor Derivatives Reveal Improved Selective Antileukemic Activity
  作者：Chanaz Salmi-Smail、Aurélie Fabre、Franck Dequiedt、Audrey Restouin、Rémy Castellano、Slaveia Garbit、Philippe Roche、Xavier Morelli、Jean Michel Brunel、Yves Collette

  DOI：10.1021/jm901358y

  日期：2010.4.22

  A series of SAHA cap derivatives was designed and prepared in good-to-excellent yields that varied from 49% to 95%. These derivatives were evaluated for their antiproliferative activity in several human cancer cell lines. Antiproliferative activity was observed for concentrations varying from 0.12 to > 100 mu M, and a molecular modeling approach of selected SAHA derivatives, based on available structural information of human HDAC8 in complex with SAHA, was performed. Strikingly, two compounds displayed up to 10-fold improved antileukemic activity with respect to SAHA; however, these compounds displayed antiproliferative activity similar to SAHA when assayed against solid tumor-derived cell lines. A 10-fold improvement in the leukemic vs peripheral blood mononuclear cell therapeutic ratio, with no evident in vivo toxicity toward blood cells, was also observed. The herein-described compounds and method of synthesis will provide invaluable tools to investigate the molecular mechanism responsible for the reported selectively improved antileukemic activity.
• Precursor-Directed Biosynthesis of Aminofulvenes: New Chalanilines from Endophytic Fungus Chalara sp.
  作者：Mahsa Khoshbakht、Jason Srey、Donovon A. Adpressa、Annika Jagels、Sandra Loesgen

  DOI：10.3390/molecules26154418

  日期：——

  The plant endophyte Chalara sp. is able to biotransform the epigenetic modifier vorinostat to form unique, aniline-containing polyketides named chalanilines. Here, we sought to expand the chemical diversity of chalaniline A-type molecules by changing the aniline moiety in the precursor vorinostat. In total, twenty-three different vorinostat analogs were prepared via two-step synthesis, and nineteen were incorporated by the fungus into polyketides. The highest yielding substrates were selected for large-scale precursor-directed biosynthesis and five novel compounds, including two fluorinated chalanilines, were isolated, purified, and structurally characterized. Structure elucidation relied on 1D and 2D NMR techniques and was supported by low- and high-resolution mass spectrometry. All compounds were tested for their bioactivity but were not active in antimicrobial or cell viability assays. Aminofulvene-containing natural products are rare, and this high-yielding, precursor-directed process allows for the diversification of this class of compounds.

  植物内生真菌 Chalara sp. 能够将表观遗传修饰剂 vorinostat 生物转化为形成独特的含苯胺的聚酮类化合物，被命名为 chalanilines。在这里，我们试图通过改变前体 vorinostat 中的苯胺基团来扩展 chalaniline A 类分子的化学多样性。总共，通过两步合成制备了二十三种不同的 vorinostat 类似物，其中十九种被真菌转化为聚酮类化合物。选择产量最高的底物进行大规模前体导向生物合成，分离、纯化并结构表征了五种新化合物，包括两种氟代 chalanilines。结构阐明依赖于一维和二维核磁共振技术，并得到低分辨率和高分辨率质谱的支持。所有化合物均进行了生物活性测试，但在抗微生物或细胞存活率测定中均不活跃。含氨基富烯的天然产物很少见，而这种高产率的前体导向过程允许对这类化合物进行多样化。