dimethyl (2-furyl)-N-(2-methoxyphenyl)aminomethylphosphonate | 1378426-53-9

• 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: dimethyl (2-furyl)-N-(2-methoxyphenyl)aminomethylphosphonate
• 英文别名: dimethyl (2-furyl)(2-methoxyphenylamino)methylphosphonate；dimethyl (2-furyl)-N-(2-methoxyphenyl)amino-methylphosphonate；N-[dimethoxyphosphoryl(furan-2-yl)methyl]-2-methoxyaniline
• CAS: 1378426-53-9
• 化学式: C₁₄H₁₈NO₅P
• 分子量: 311.274
• InChiKey: XTHSGXOXKGREIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  69.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  亚磷酸二甲酯 、 1-(呋喃-2-基)-N-(2-甲氧基苯基)甲亚胺 在 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以71%的产率得到dimethyl (2-furyl)-N-(2-methoxyphenyl)aminomethylphosphonate
  参考文献：
  名称：

  Synthesis of new N-arylamino(2-furyl)methylphosphonic acid diesters, and in vitro evaluation of their cytotoxicity against esophageal cancer cells

  摘要：

  N-Furfurylideneanilines and N-arylamino(2-furyl)methylphosphonates with tolyl and anisyl moieties were synthesized by the addition of phosphites to azomethine bond of corresponding Schiff bases and their NMR spectroscopic properties were investigated. Then, they were analyzed in the point of view of their influence on KYSE 30, KYSE 150, and KYSE 270 esophageal cancer cell lines and on immortalized esophageal cell line HET 1 A as a control group. Toxicity was evaluated by MTT assay. Among 11 compounds, a few of them demonstrated influence on cancer cells being neutral toward the control, but only one aminophosphonate had IC50 lower than 100 mu M and acted as a potential anticancer drug. Some approaches to structure-activity relation were performed.

  DOI：

  10.1007/s00044-012-0065-3

文献信息

• Dimethyl (2-Furyl)-<i>N</i>-(2-Methoxyphenyl)Aminomethylphosphonate Induces Apoptosis in Esophageal Squamous Cancer Cells. Structure Versus Activity of its Selected Analogs
  作者：Anna Agnieszka Klimczak、Agnieszka Matusiak、Jarosław Lewkowski、Jan Bitner、Janusz Szemraj、Renata Kontek

  DOI：10.1080/10426507.2014.965821

  日期：2015.7.3

  Cytotoxicities of several new aminophosphonic compounds bearing 2-furyl moiety 2b-d and 3a-c on KYSE 30, 150, and 270 esophageal cancer cell lines are reported here. The qualitative study on correlations between the structure and cytotoxic activity of furan-deriving aminophosphonates has been performed.Dimethyl (2-furyl)-N-(2-methoxyphenyl)aminomethylphosphonate (2a), which has been previously shown to have the interesting values of cytotoxicity on these esophageal cancer cell lines was tested and found to induce apoptosis. The analyses of correlations between apoptosis, necrosis, and viability were also performed.
• Synthesis of new N-arylamino(2-furyl)methylphosphonic acid diesters, and in vitro evaluation of their cytotoxicity against esophageal cancer cells
  作者：Anna Agnieszka Klimczak、Agnieszka Kuropatwa、Jarosław Lewkowski、Janusz Szemraj

  DOI：10.1007/s00044-012-0065-3

  日期：2013.2

  N-Furfurylideneanilines and N-arylamino(2-furyl)methylphosphonates with tolyl and anisyl moieties were synthesized by the addition of phosphites to azomethine bond of corresponding Schiff bases and their NMR spectroscopic properties were investigated. Then, they were analyzed in the point of view of their influence on KYSE 30, KYSE 150, and KYSE 270 esophageal cancer cell lines and on immortalized esophageal cell line HET 1 A as a control group. Toxicity was evaluated by MTT assay. Among 11 compounds, a few of them demonstrated influence on cancer cells being neutral toward the control, but only one aminophosphonate had IC50 lower than 100 mu M and acted as a potential anticancer drug. Some approaches to structure-activity relation were performed.