2-氰基-N-环己基-乙酰胺 | 15029-38-6

• 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
• 中文名称: 2-氰基-N-环己基-乙酰胺
• 中文别名: 2-氰基-N-环己基乙酰胺
• 英文名称: 2-cyano-N-cyclohexylacetamide
• 英文别名: Cyanessigsaeure-cyclohexylamid；N-cyclohexylcyanoacetamide
• CAS: 15029-38-6
• 化学式: C₉H₁₄N₂O
• mdl: MFCD00228093
• 分子量: 166.223
• InChiKey: RURWLUVLDBYUEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.777
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  2-氰基-N-环己基-乙酰胺 在 potassium carbonate 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 53.0h， 生成 2-cyano-N-cyclohexyl-2-(2,4-dinitrophenyl)acetamide compound with triethylamine (1:1)
  参考文献：
  名称：

  Synthesis, structural and spectral features of CH-Acids: Amides of 2,4-dinitrophenylcyanoacetic acid and their ammonium salts

  摘要：

  New N-methylmorpholinium and triethylammonium salts of 2,4-dinitrophenylcyanoacetic acid were obtained. Their electronic and spatial structure was studied by IR, NMR spectroscopy (including two-dimensional correlation spectra HMQC and HMBC), as well as by XRD analysis.

  DOI：

  10.1134/s1070363213050137
• 作为产物：
  描述：

  环己胺 、 氰乙酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 DCM 为溶剂， 反应 24.0h， 以68%的产率得到2-氰基-N-环己基-乙酰胺
  参考文献：
  名称：

  WO2008/99145

  摘要：

  公开号：

文献信息

• Synthesis of resveratrol acrylamides derivatives and biological evaluation of their anti-proliferative effect on cancer cell lines
  作者：Ban-Feng Ruan、Si-Qi Wang、Xiao-Lin Ge、Ri-Sheng Yao

  DOI：10.2174/15701808113109990057

  日期：2013.11

  A new series of resveratrol acrylamides amine derivatives was designed, synthesized, and evaluated for their anti-proliferative activity against three cancer cell lines including human chronic myelocytic leukemia cell K562, human hepatoma HuH-7 and human lung carcinoma A549. Most of the compounds showed superior activity against three cell lines when compared to parent resveratrol. C13 had the best anti-tumor activity against the HuH-7 cell line and its IC50 was 4.5 μmol/L; C16 had the best anti-tumor activity against the K562 cell line and its IC50 was 2.9 μmol/L; C18 had the best anti-tumor activity against the A549 cell line and its IC50 was 3.8 μmol/L. It could be seen that the activity of the aromatic amine derivatives was better than the fatty amine derivatives by analyzing the experimental data.

  设计、合成并评价了一系列白藜芦醇丙烯酰胺胺衍生物对三种癌细胞株的抗增殖活性，包括人慢性髓细胞白血病细胞K562、人肝癌HuH-7和人肺癌A549。与母体白藜芦醇相比，大多数化合物对三种细胞株表现出更强的活性。C13对HuH-7细胞株具有最佳的抗肿瘤活性，其IC50为4.5 μmol/L; C16对K562细胞株具有最佳的抗肿瘤活性，其IC50为2.9 μmol/L；C18对A549细胞株具有最佳的抗肿瘤活性，其IC50为3.8 μmol/L。通过分析实验数据可以发现，芳香胺衍生物的活性优于脂肪胺衍生物。
• Efficient synthesis of new butenolides by subsequent reactions: application for the synthesis of original iminolactones, bis-iminolactones and bis-lactones
  作者：Nawel Cheikh、Nathalie Bar、Nourredine Choukchou-Braham、Bachir Mostefa-Kara、Jean-François Lohier、Jana Sopkova、Didier Villemin

  DOI：10.1016/j.tet.2010.12.062

  日期：2011.2

  We have developed the synthesis of twenty four new iminolactones, bis-iminolactones and bis-lactones by subsequent esterification–condensation or addition–condensation reactions according to two strategies from α-hydroxyketones. The X-ray diffraction data of a bis-iminolactone is described and present an interesting helical column packing.

  根据α-羟基酮的两种策略，我们通过随后的酯化-缩合或加成-缩合反应，开发了二十四种新的亚氨基内酯，双亚氨基内酯和双内酯。描述了双亚氨基内酯的X射线衍射数据，并给出了令人感兴趣的螺旋柱填料。
• Synthesis and some chemical transformations of novel functionalized 2-imino-2,5-dihydrofurans
  作者：A. A. Avetisyan、L. V. Karapetyan、M. D. Tadevosyan

  DOI：10.1007/s11172-010-0192-2

  日期：2010.5

  Hitherto unknown functionalized 2-imino-3-(N-cyclohexylcarbamoyl)-2,5-dihydrofurans were synthesized by the reactions of tertiary α-hydroxy ketones with N-cyclohexyl(cyano-acetamide). Several reactions of thus synthesized compounds at the imino group were carried out.

  迄今为止未知的官能化 2-亚氨基-3-(N-环己基氨基甲酰基)-2,5-二氢呋喃是通过叔 α-羟基酮与 N-环己基（氰基乙酰胺）的反应合成的。在亚氨基上进行由此合成的化合物的若干反应。
• A Convenient Synthesis Of Substituted 3-Pyrrolin-2-ones from α-Cetols
  作者：Gaguik Melikian、Francis Rouessac、Christian Alexandre

  DOI：10.1080/00397919308013792

  日期：1993.11

  Abstract A simple and efficient method for the preparation of the title compounds is described from cyanoacetamides and 3-hydroxy-3-methyl-2-butanone in the presence of sodium ethylate at room temperature. The 3-carboxamido-N-alkyl-4, 5, 5-trimethyl-5-dihy dro-2H-pyrrol-2-ones lead to unsaturated derivatives by condensation with aldehydes, while hydrogenation give rise to the corresponding pyrrolidin-2-ones

  摘要 描述了在乙醇钠存在下，在室温下，由氰基乙酰胺和 3-羟基-3-甲基-2-丁酮制备标题化合物的一种简单有效的方法。3-甲酰胺基-N-烷基-4, 5, 5-trimethyl-5-dihy dro-2H-pyrrol-2-ones 通过与醛缩合生成不饱和衍生物，而氢化生成相应的 pyrrolidin-2-ones .
• Structure–Activity Relationship of SPOP Inhibitors against Kidney Cancer
  作者：Ze Dong、Zhen Wang、Zhong-Qiang Guo、Shouzhe Gong、Tao Zhang、Jiang Liu、Cheng Luo、Hualiang Jiang、Cai-Guang Yang

  DOI：10.1021/acs.jmedchem.0c00161

  日期：2020.5.14

  Previously, we elucidated that the oncogenic SPOP-signaling pathway in ccRCC could be suppressed by 6b that inhibits SPOP-mediated protein interactions. Herein, we have established a structure-activity relationship for 6b analogues as SPOP inhibitors. Compound 6lc suppresses the viability and inhibits the colony formation of ccRCC cell lines driven by cytoplasmic SPOP, superior to 6b. Compound 6lc binds

  在几乎所有的透明细胞肾细胞癌（ccRCC）中，斑点型POZ蛋白（SPOP）在细胞核中过度表达，并在细胞质中错位，从而导致肾脏肿瘤发生。先前，我们阐明了ccRCC中的致癌SPOP信号通路可能被抑制SPOP介导的蛋白质相互作用的6b所抑制。在这里，我们已经建立了6b类似物作为SPOP抑制剂的构效关系。化合物6lc抑制了活力，并抑制了优于6b的细胞质SPOP驱动的ccRCC细胞系的集落形成。化合物6lc在体外与SPOP蛋白结合，并破坏HEK293T细胞中SPOP与磷酸酶和肌腱蛋白同源物（PTEN）的结合，这引起了可观察到的现象：PTEN泛素化的下降，当ccRCC细胞系以剂量反应方式暴露于6lc时，PTEN和双重特异性磷酸酶7的水平升高，磷酸化AKT和ERK的水平降低。两者合计，化合物6lc是对抗肾肿瘤发生的有效候选物。