7-oxoheptanoic acid phenylamide | 728890-58-2

• 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: 7-oxoheptanoic acid phenylamide
• 英文别名: 7-oxo-N-phenylheptanamide
• CAS: 728890-58-2
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: FNXXADZKYJCMMU-UHFFFAOYSA-N

物化性质

• 沸点：
  420.1±28.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-oxoheptanoic acid phenylamide 在 sodium tetrahydroborate 、 正丁基锂 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 69.83h， 生成
  参考文献：
  名称：

  Effects of E/Z Configuration of Fluoroalkene-containing HDAC Inhibitors on Selectivity for HDAC Isoforms

  摘要：

  组蛋白去乙酰化酶（HDAC）抑制剂属于一种潜在的抗癌剂的新类别。通过针对特定的HDAC同种型，可能有助于减少一些毒性。在这里，分析了含有氟烯烃的立体异构HDAC抑制剂对HDAC同种型的特异性。Z-形式1（Z）对HDAC表现出高亲和力，而E-异构体1（E）对HDAC1和HDAC4的亲和力较低。这些数据表明，将E/Z构型的烯烃引入HDAC抑制剂可以成为开发同种型选择性HDAC抑制剂的新策略。

  DOI：

  10.1246/cl.130243
• 作为产物：
  描述：

  7-氧代-7-(苯基氨基)庚酸 在 lithium aluminium tetrahydride 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 7-oxoheptanoic acid phenylamide
  参考文献：
  名称：

  Dendritic polypeptide-based nanocarriers for the delivery of therapeutic agents

  摘要：

  揭示了用于将治疗剂传递到细胞中的树突多肽，以及它们的制备方法。这些树突多肽可作为药物、siRNA、aptamers和质粒DNA的载体，在治疗各种疾病，包括癌症方面发挥作用。

  公开号：

  US09943606B2

文献信息

• Synthesis and biological evaluation of aziridin-1-yl oxime-based vorinostat analogs as anticancer agents
  作者：Anna Nikitjuka、Irina Shestakova、Nadezhda Romanchikova、Aigars Jirgensons

  DOI：10.1007/s10593-015-1752-z

  日期：2015.7

  The suberoyl anilide hydroxamic acid (vorinostat) analogs with the aziridin-1-yl oxime moiety as a possible metal chelating functionality have been synthesized. Their biological activity and stability under physiological conditions have been evaluated. Although some of the synthesized compounds demonstrated high antiproliferative activity against human HT1080 fibrosarcoma (HT1080, IC50 0.3-7.7 mu M) comparable to vorinostat (HT1080, IC50 2.4 mu M), they showed only weak histone deacetylase inhibition activity in HeLa cell line extracts.
• Design and synthesis of non-hydroxamate histone deacetylase inhibitors: identification of a selective histone acetylating agent
  作者：Takayoshi Suzuki、Azusa Matsuura、Akiyasu Kouketsu、Shinya Hisakawa、Hidehiko Nakagawa、Naoki Miyata

  DOI：10.1016/j.bmc.2005.04.002

  日期：2005.7

  A series of suberoylanilide hydroxamic acid (SAHA)-based non-hydroxamates was designed, synthesized, and evaluated for their histone deacetylase (HDAC) inhibitory activity. Among these, methyl sulfoxide 15 inhibited HDACs in enzyme assays and caused hyperacetylation of histone H4 while not inducing the accumulation of acetylated alpha-tubulin in HCT116 cells. (c) 2005 Elsevier Ltd. All rights reserved.
• Thiol-based SAHA analogues as potent histone deacetylase inhibitors
  作者：Takayoshi Suzuki、Akiyasu Kouketsu、Azusa Matsuura、Arihiro Kohara、Shin-ichi Ninomiya、Kohfuku Kohda、Naoki Miyata

  DOI：10.1016/j.bmcl.2004.03.063

  日期：2004.6

  In order to find novel nonhydroxamate histone deacetylase (HDAC) inhibitors, a series of thiol-based compounds modeled after suberoylanilide hydroxamic acid (SAHA) was synthesized, and their inhibitory effect on HDACs was evaluated. Compound 6, in which the hydroxamic acid of SAHA was replaced by a thiol, was found to be as potent as SAHA, and optimization of this series led to the identification of HDAC inhibitors more potent than SAHA. (C) 2004 Elsevier Ltd. All rights reserved.