乙基(E,E,Z)-十四碳-2,4,8-三烯酸酯 | 82720-47-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 乙基(E,E,Z)-十四碳-2,4,8-三烯酸酯
• 英文名称: N,N,N',N'-tetramethyl-N''-(4-nitrophenyl)phosphoric triamide
• 英文别名: N-[bis(dimethylamino)phosphoryl]-4-nitroaniline
• CAS: 82720-47-6
• 化学式: C₁₀H₁₇N₄O₃P
• 分子量: 272.244
• InChiKey: PHQPQYFWZURLSV-UHFFFAOYSA-N

物化性质

• 熔点：
  215 °C(Solv: methanol (67-56-1))
• 沸点：
  377.1±44.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  81.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙基(E,E,Z)-十四碳-2,4,8-三烯酸酯 在 盐酸 、 铁粉 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以92%的产率得到4-N-[bis(dimethylamino)phosphoryl]benzene-1,4-diamine
  参考文献：
  名称：

  Potential antitumor agents. 37. Organophosphorus derivatives of 9-anilinoacridine

  摘要：

  A series of 9-anilinoacridine derivatives substituted in the anilino ring with a variety of phosphoramide and related substitutents has been prepared, and the antitumor activity has been evaluated both in vivo and in vitro against the L1210 or P-388 mouse leukemia systems. The DNA-binding properties were measured using the ethidium displacement method, and the structural requirements for strong binding were found to differ from those for antileukemic activity. For high biological activity a marked preference for oxygen-containing substituents on the phosphorus atom was noted, while for high DNA binding a requirement for nitrogen-containing or cyclized substituents was observed. The most active congeners, as assayed in both in vitro and in vivo systems, were comparable in activity to the clinically utilized anilinoacridine derivative N-[4'-(9-acridinylamino)-3'-methoxyphenyl]methanesulfonamide (m-AMSA, amsacrine).

  DOI：

  10.1021/jm00352a027
• 作为产物：
  描述：

  N-(4-nitrophenyl)phosphoramidic dichloride 、 盐酸二甲胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以35%的产率得到乙基(E,E,Z)-十四碳-2,4,8-三烯酸酯
  参考文献：
  名称：

  Potential antitumor agents. 37. Organophosphorus derivatives of 9-anilinoacridine

  摘要：

  A series of 9-anilinoacridine derivatives substituted in the anilino ring with a variety of phosphoramide and related substitutents has been prepared, and the antitumor activity has been evaluated both in vivo and in vitro against the L1210 or P-388 mouse leukemia systems. The DNA-binding properties were measured using the ethidium displacement method, and the structural requirements for strong binding were found to differ from those for antileukemic activity. For high biological activity a marked preference for oxygen-containing substituents on the phosphorus atom was noted, while for high DNA binding a requirement for nitrogen-containing or cyclized substituents was observed. The most active congeners, as assayed in both in vitro and in vivo systems, were comparable in activity to the clinically utilized anilinoacridine derivative N-[4'-(9-acridinylamino)-3'-methoxyphenyl]methanesulfonamide (m-AMSA, amsacrine).

  DOI：

  10.1021/jm00352a027

文献信息

• REWCASTLE, G. W.;BAGULEY, B. C.;CAIN, B. F., J. MED. CHEM., 1982, 25, N 10, 1231-1235
  作者：REWCASTLE, G. W.、BAGULEY, B. C.、CAIN, B. F.

  DOI：——

  日期：——
• Potential antitumor agents. 37. Organophosphorus derivatives of 9-anilinoacridine
  作者：Gordon W. Rewcastle、Bruce C. Baguley、Bruce F. Cain

  DOI：10.1021/jm00352a027

  日期：1982.10

  A series of 9-anilinoacridine derivatives substituted in the anilino ring with a variety of phosphoramide and related substitutents has been prepared, and the antitumor activity has been evaluated both in vivo and in vitro against the L1210 or P-388 mouse leukemia systems. The DNA-binding properties were measured using the ethidium displacement method, and the structural requirements for strong binding were found to differ from those for antileukemic activity. For high biological activity a marked preference for oxygen-containing substituents on the phosphorus atom was noted, while for high DNA binding a requirement for nitrogen-containing or cyclized substituents was observed. The most active congeners, as assayed in both in vitro and in vivo systems, were comparable in activity to the clinically utilized anilinoacridine derivative N-[4'-(9-acridinylamino)-3'-methoxyphenyl]methanesulfonamide (m-AMSA, amsacrine).