Diethyl[(2-furyl)(4-methylphenylamino)methyl]phosphonate | 892229-26-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: Diethyl[(2-furyl)(4-methylphenylamino)methyl]phosphonate
• 英文别名: Diethyl [(furan-2-YL)[(4-methylphenyl)amino]methyl]phosphonate；N-[diethoxyphosphoryl(furan-2-yl)methyl]-4-methylaniline
• CAS: 892229-26-4
• 化学式: C₁₆H₂₂NO₄P
• 分子量: 323.329
• InChiKey: GNTTZSCWDITSAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  60.7
• 氢给体数：
  1
• 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 、 亚磷酸二乙酯 在 cadmium(II) iodide 作用下， 以 苯 为溶剂， 反应 3.0h， 以77%的产率得到Diethyl[(2-furyl)(4-methylphenylamino)methyl]phosphonate
  参考文献：
  名称：

  Synthesis, NMR characterization and in vitro antitumor evaluation of new aminophosphonic acid diesters

  摘要：

  The synthesis of three novel m-aminophosphonic acid diesters N,N-dimethyl-[N'-methy](diethoxyphosphonyl)-(2-furyl)1-1,3-diaminopropane, p-IN-methyl(diethoxyphosphonyl)-(2-furyl)]toluidine and p-[N-methyl(diethoxyphosphonyl)-(4-dimethylaminophenyl)]toluidine through an addition of diethyl phosphite to N,N-dimethyl-N'-furfurylidene-1,3-diaminopropane, N-furfurylidene-p-toluidine and N-(4-dimethylaminobenzylidene)-p-toluidine, respectively, is reported. The alpha-aminophosphonates have been characterized by elemental analysis, IR and NMR (H-1, C-13 and P-31) spectra. The compounds were tested for anti proliferative effects against 4 human leukemic cell lines, namely LAMA-84, K-562 (chronic myeloid leukemias), HL-60 (acute promyelocyte leukemia) and HL-60/Dox (multi-drug-resistant sub-line, characterized by overexpression of MRP-1 (ABC-C1)) and were found to exert concentration-dependent cytotoxic effects. A representative aminophosphonate compound was shown to induce oligonucleosomal DNA fragmentation which implies that the induction of cell death through apoptosis plays an important role for its cytotoxicity mode of action. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.03.017

文献信息

• Synthesis, NMR characterization and in vitro antitumor evaluation of new aminophosphonic acid diesters
  作者：I. Kraicheva、A. Bogomilova、I. Tsacheva、G. Momekov、K. Troev

  DOI：10.1016/j.ejmech.2009.03.017

  日期：2009.8

  The synthesis of three novel m-aminophosphonic acid diesters N,N-dimethyl-[N'-methy](diethoxyphosphonyl)-(2-furyl)1-1,3-diaminopropane, p-IN-methyl(diethoxyphosphonyl)-(2-furyl)]toluidine and p-[N-methyl(diethoxyphosphonyl)-(4-dimethylaminophenyl)]toluidine through an addition of diethyl phosphite to N,N-dimethyl-N'-furfurylidene-1,3-diaminopropane, N-furfurylidene-p-toluidine and N-(4-dimethylaminobenzylidene)-p-toluidine, respectively, is reported. The alpha-aminophosphonates have been characterized by elemental analysis, IR and NMR (H-1, C-13 and P-31) spectra. The compounds were tested for anti proliferative effects against 4 human leukemic cell lines, namely LAMA-84, K-562 (chronic myeloid leukemias), HL-60 (acute promyelocyte leukemia) and HL-60/Dox (multi-drug-resistant sub-line, characterized by overexpression of MRP-1 (ABC-C1)) and were found to exert concentration-dependent cytotoxic effects. A representative aminophosphonate compound was shown to induce oligonucleosomal DNA fragmentation which implies that the induction of cell death through apoptosis plays an important role for its cytotoxicity mode of action. (C) 2009 Elsevier Masson SAS. All rights reserved.