(2-furyl)-N-(4-methylphenyl)aminomethylphosphonic acid | 1448989-21-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2-furyl)-N-(4-methylphenyl)aminomethylphosphonic acid
• 英文别名: [Furan-2-yl-(4-methylanilino)methyl]phosphonic acid；[furan-2-yl-(4-methylanilino)methyl]phosphonic acid
• CAS: 1448989-21-6
• 化学式: C₁₂H₁₄NO₄P
• 分子量: 267.221
• InChiKey: FYRIBPNAWZODCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  82.7
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(呋喃-2-基)-N-(4-甲基苯基)甲亚胺 在 三甲基溴硅烷 、 亚磷酸二乙酯 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (2-furyl)-N-(4-methylphenyl)aminomethylphosphonic acid
  参考文献：
  名称：

  Dimethyl (2-Furyl)-N-(2-Methoxyphenyl)Aminomethylphosphonate Induces Apoptosis in Esophageal Squamous Cancer Cells. Structure Versus Activity of its Selected Analogs

  摘要：

  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.

  DOI：

  10.1080/10426507.2014.965821

文献信息

• Phytotoxicity of New Furan-derived Aminophosphonic Acids, <i>N</i>-Aryl Furaldimines and 5-Nitrofuraldimine
  作者：Agnieszka Matusiak、Jarosław Lewkowski、Piotr Rychter、Robert Biczak

  DOI：10.1021/jf402401z

  日期：2013.8.14

  The aim of this work was to synthesize selected furaldimines and their aminophosphonic derivatives and evaluation the phytotoxicity of new obtained products according to OECD 208 Guideline. Four Schiff bases, N-furfurylidene-p-anisidine (la), N-furfurylidene-p-toluidine (1b), N-furfurylidene-benzhydrylamine (1c), and N-(2-nitrofurfurylidene)-p-toluidine (Id) were synthesized and three new furan-derived N-substituted aminomethylphosphonic acids, namely: 2-furyl N-(p-methoxyphenyl)-aminomethylphosphonic acid (2a), 2-furyl N-(p-methylphenyl)-aminomethylphosphonic acid (2b) and 2-furyl N-(diphenylmethyl)-aminomethylphosphonic acid (2c) were synthesized by the addition of in situ generated bis-(trimethylsilyl) phosphite to azomethine bond of corresponding Schiff bases 1a-c. Three Schiff bases 1a-b and 1d as well as all three aminophosphonic acids 2a-c were analyzed in regard with their phytotoxicity toward two plants, radish (Raphanus sativus) and oat (Avena sativa).It has been found that tested N-furfurylidene-p-anisidine (la), N-(2-nitrofurfurylidene)-p-toluidine (Id) and aminophosphonic acids 2a c are toxic for selected plants. N-furfurylidene-p-toluidine (1b) did not show any ecotoxicological impact in used plant growth test.