N-(4-nitrophenyl)diethylphosphonoacetamide | 1370556-90-3

• 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-nitrophenyl)diethylphosphonoacetamide
• 英文别名: 2-diethoxyphosphoryl-N-(4-nitrophenyl)acetamide
• CAS: 1370556-90-3
• 化学式: C₁₂H₁₇N₂O₆P
• 分子量: 316.251
• InChiKey: XCCXDRPHJLTSJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(4-nitrophenyl)diethylphosphonoacetamide 、 1-[(3-Methyl-1,2-oxazol-5-yl)methyl]indole-2,3-dione 在 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 8.0h， 以76%的产率得到(E)-2-(1-((3-methylisoxazol-5-yl)methyl)-2-oxoindolin-3-ylidene)-N-(4-nitrophenyl)acetamide
  参考文献：
  名称：

  Synthesis and evaluation of 3-ylideneoxindole acetamides as potent anticancer agents

  摘要：

  Indirubin, an active component in the traditional Chinese medicine formula Danggui Longhui Wan, shows promising anticancer effects. Meisoindigo is an analog derived from indirubin, which is less toxic and appears to be even more potent against cancer. In considering meisoindigo as a structural template for the development of new drugs, we designed and synthesized a series of 3-ylideneoxindole acetamides as novel anticancer agents. The acetamides were then evaluated for in vitro and in vivo anticancer activities. The 3-ylideneoxindole acetamides were found to have better anticancer activity than was indirubin-3'-oxime in several cancer cell lines and also displayed a spectrum of activity similar to that of the drug candidate roscovitine, a CDK inhibitor. Among the 3-ylideneoxindole acetamides, compound 10 showed particularly good efficacy. Cell cycle analysis further revealed that compound 10 arrested cells in the G1 phase and caused an increase in the sub-G1 population, indicating that the apoptosis pathway had been induced. In addition, exposure of cells to compound 10 led to the upregulation of the cell-cycle regulator cyclin D1, which was sustained at a high level. In contrast, the same compound induced a short-term elevation in the level of cyclin E, which was followed by a rapid decrease and the attenuation of Rb phosphorylation. Furthermore, a docking model suggests that compound 10 binds to the active site of CDK4. In testing the therapeutic potency of compound 10 on CT26-xenografted BALB/c mice, a significant reduction in tumor size comparable to that of cisplatin was found when administrated via the i.p. route. The mice presented no loss of body weight, indicating that this compound possesses low toxicity. In the future, we are planning in vivo investigations of these new active anticancer agents to better elucidate active mechanisms at the cellular level and thus benefit the development of anticancer therapies. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.062
• 作为产物：
  描述：

  N-(4-nitrophenyl)bromoacetamide 、 亚磷酸三乙酯 在 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.03h， 以100%的产率得到N-(4-nitrophenyl)diethylphosphonoacetamide
  参考文献：
  名称：

  Microwave-Enhanced Synthesis of Phosphonoacetamides

  摘要：

  An efficient microwave protocol is described for the Michaelis-Arbuzov synthesis of secondary and tertiary N-aryl (and alkyl) (diethylphosphono) acetamides 1, by reaction of chloro- and bromoacetamides with triethyl phosphite in the presence of catalytic amounts of sodium iodide. Remarkable acceleration of the reaction (minutes vs. several hours) over conventional heating was achieved, together with improved product yields and purity, when bromoacetamides were employed as the substrates. Chloroacetamides were comparatively less reactive, leading to satisfactory yields only when a high excess of the reagent was employed.

  DOI：

  10.1080/00397911.2010.530377