dimethyl N-(4-nitrobenzoyl)phosphoramidate | 24856-35-7

• 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 N-(4-nitrobenzoyl)phosphoramidate
• 英文别名: (4-nitro-benzoyl)-amidophosphoric acid dimethyl ester；(4-Nitro-benzoyl)-amidophosphorsaeure-dimethylester；Phosphorsaeure-dimethylester-<4-nitro-benzamid>；Phosphorsaeure-dimethylester-(4-nitro-benzoyl)-amid；N-dimethoxyphosphoryl-4-nitrobenzamide
• CAS: 24856-35-7
• 化学式: C₉H₁₁N₂O₆P
• 分子量: 274.17
• InChiKey: XRKUEBNIXLQUCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl N-(4-nitrobenzoyl)phosphoramidate 在 盐酸 、 ammonium hydroxide 、 铁粉 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 生成 4-(acridin-9-ylamino)-N-dimethoxyphosphorylbenzamide
  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-nitrobenzoylphosphoramidic dichloride 在 sodium methylate 作用下， 生成 dimethyl N-(4-nitrobenzoyl)phosphoramidate
  参考文献：
  名称：

  Kirsanow; Makitra, Zhurnal Obshchei Khimii, 1958, vol. 28, p. 35,38; engl. Ausg. S. 35, 37

  摘要：

  DOI：

文献信息

• Derkach,G.I. et al., Journal of general chemistry of the USSR, 1960, vol. 30, p. 3359 - 3363
  作者：Derkach,G.I. et al.

  DOI：——

  日期：——
• Derkatsch, Zhurnal Obshchei Khimii, 1959, vol. 29, p. 241,242, 243; engl. Ausg. S. 244, 245
  作者：Derkatsch

  DOI：——

  日期：——
• 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：——