diphenyl (2-furyl)(4-methoxyphenylamino)methylphosphonate | 1378426-58-4

• 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: diphenyl (2-furyl)(4-methoxyphenylamino)methylphosphonate
• 英文别名: diphenyl (2-furyl)-N-(4-methoxyphenyl)-aminomethylphosphonate；N-[diphenoxyphosphoryl(furan-2-yl)methyl]-4-methoxyaniline
• CAS: 1378426-58-4
• 化学式: C₂₄H₂₂NO₅P
• 分子量: 435.416
• InChiKey: KQRGICZNLAZALR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  糠醛 在 三氟乙酸 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 96.0h， 生成 diphenyl (2-furyl)(4-methoxyphenylamino)methylphosphonate
  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

• 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.