1-(4-methyl-1,4-diazepan-1-yl)tetradecan-1-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂卓
• 英文名称: 1-(4-methyl-1,4-diazepan-1-yl)tetradecan-1-one
• 化学式: C₂₀H₄₀N₂O
• 分子量: 324.55
• InChiKey: IWDZBAZTCIQGFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-methyl-1,4-diazepan-1-yl)tetradecan-1-one 在 lithium aluminium tetrahydride 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到1-Methyl-4-tetradecyl-1,4-diazepane
  参考文献：
  名称：

  长烷基链酰胺，胺及其衍生物对犬round虫幼虫的杀线虫活性。

  摘要：

  检查了具有长烷基链的酰胺和胺对犬round虫第二阶段幼虫的杀线虫活性。在氮上具有较小取代基的长链酰基酰胺显示出更强的活性，环状胺酰胺的活性强于无环酰胺。在一系列同源酰胺中，活性取决于烷基链长：在最佳链长处达到最大值，而在较短和较长的同系物中均降低。通过使用双线性模型分析了同系物的活性与疏水性之间的关系。对于所有中性酰胺，提供最大活性的化合物的疏水性均相似，但分子中具有额外胺基的酰胺具有不同的值。具有长烷基链的叔胺及其盐也具有与相应酰胺相当的杀线虫活性。这些盐以低于其临界胶束浓度的浓度杀死幼虫，表明它们表现为杀线虫作用的单个分子。

  DOI：

  10.1248/cpb.40.3234
• 作为产物：
  描述：

  肉豆蔻酸 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 1-(4-methyl-1,4-diazepan-1-yl)tetradecan-1-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel aliphatic amido/sulfonamido-quaternary ammonium salts as antitumor agents

  摘要：

  RhoB, one of the upstream signaling proteins of the phosphatidylinositol-3-kinase (PI3K)/Akt pathway, is frequently mutated in human cancer. Based on a piperazine alkyl derivative that induced apoptosis via up-regulation of RhoB, we synthesized novel aliphatic amido/sulfonamido-quaternary ammonium salts and evaluated their biological activities using an in vitro growth inhibition assay and RhoB promoter assay in human cancer cells. Compound 3a was the most promising anticancer agent in the series, based upon its potent growth inhibition via RhoB-mediated signaling. These novel aliphatic amido/sulfonamido- quaternary ammonium salts may be useful as a platform for development of anticancer chemotherapeutic agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.027

文献信息

• Studies on Crude Drugs Effective on Visceral Larva Migrans. Part XVI. Nematocidal Activity of Long Alkyl Chain Amides, Amines, and Their Derivatives on Dog Roundworm Larvae.
  作者：Fumiyuki KIUCHI、Satomi NISHZAWA、Hiromi KAWANISHI、Sayuri KINOSHITA、Hisanao OHSIMA、Akiyo UCHITANI、Noriko SEKINO、Miki ISHIDA、Kaoru KONDO、Yoshisuke TSUDA

  DOI：10.1248/cpb.40.3234

  日期：——

  activity of amides and amines having a long alkyl chain against the second-stage larva of dog roundworm, Toxocara canis, was examined. Long chain acyl amides with smaller substituents on the nitrogen showed stronger activity and the activity of cyclic amine amides was stronger than that of acyclic ones. In a series of homologous amides, the activity was dependent on the alkyl chain length: it reached

  检查了具有长烷基链的酰胺和胺对犬round虫第二阶段幼虫的杀线虫活性。在氮上具有较小取代基的长链酰基酰胺显示出更强的活性，环状胺酰胺的活性强于无环酰胺。在一系列同源酰胺中，活性取决于烷基链长：在最佳链长处达到最大值，而在较短和较长的同系物中均降低。通过使用双线性模型分析了同系物的活性与疏水性之间的关系。对于所有中性酰胺，提供最大活性的化合物的疏水性均相似，但分子中具有额外胺基的酰胺具有不同的值。具有长烷基链的叔胺及其盐也具有与相应酰胺相当的杀线虫活性。这些盐以低于其临界胶束浓度的浓度杀死幼虫，表明它们表现为杀线虫作用的单个分子。
• Design, synthesis and biological evaluation of novel aliphatic amido/sulfonamido-quaternary ammonium salts as antitumor agents
  作者：Doona Song、Jee Sun Yang、Seo Joong Kim、Bo-Kyung Kim、Song-Kyu Park、Misun Won、Kiho Lee、Hwan Mook Kim、Kang-Yell Choi、Kyeong Lee、Gyoonhee Han

  DOI：10.1016/j.bmc.2012.11.027

  日期：2013.2

  RhoB, one of the upstream signaling proteins of the phosphatidylinositol-3-kinase (PI3K)/Akt pathway, is frequently mutated in human cancer. Based on a piperazine alkyl derivative that induced apoptosis via up-regulation of RhoB, we synthesized novel aliphatic amido/sulfonamido-quaternary ammonium salts and evaluated their biological activities using an in vitro growth inhibition assay and RhoB promoter assay in human cancer cells. Compound 3a was the most promising anticancer agent in the series, based upon its potent growth inhibition via RhoB-mediated signaling. These novel aliphatic amido/sulfonamido- quaternary ammonium salts may be useful as a platform for development of anticancer chemotherapeutic agents. (C) 2012 Elsevier Ltd. All rights reserved.