N-[bis(2-chloroethyl)amino-[2-(4-nitrophenyl)sulfanylethoxy]phosphoryl]-2-chloro-N-(2-chloroethyl)ethanamine | 735327-48-7

• 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: N-[bis(2-chloroethyl)amino-[2-(4-nitrophenyl)sulfanylethoxy]phosphoryl]-2-chloro-N-(2-chloroethyl)ethanamine
• CAS: 735327-48-7
• 化学式: C₁₆H₂₄Cl₄N₃O₄PS
• 分子量: 527.236
• InChiKey: PVIKMPNQIMEGON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[bis(2-chloroethyl)amino-[2-(4-nitrophenyl)sulfanylethoxy]phosphoryl]-2-chloro-N-(2-chloroethyl)ethanamine 在 ammonium molybdate 、 双氧水 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以49%的产率得到N-[bis(2-chloroethyl)amino-[2-(4-nitrophenyl)sulfonylethoxy]phosphoryl]-2-chloro-N-(2-chloroethyl)ethanamine
  参考文献：
  名称：

  Sulfonyl-Containing Aldophosphamide Analogues as Novel Anticancer Prodrugs Targeted against Cyclophosphamide-Resistant Tumor Cell Lines

  摘要：

  A series of sulfonyl-group containing analogues of aldophosphamide (Aldo) were synthesized as potential anticancer prodrugs that liberate the cytotoxic phosphoramide mustards (PM, IPM, and tetrakis-PM) via beta-elimination, a nonenzymatic activation mechanism. Kinetic studies demonstrated that all these compounds spontaneously liberate phosphoramide mustards with half-lives in the range of 0.08-15.2 h under model physiological conditions in 0.08 M phosphate buffer at pH 7.4 and 37 degreesC. Analogous to Aldo, the rates of beta-elimination in all compounds was enhanced in reconstituted human plasma under same conditions. The compounds were more potent than the corresponding phosphoramide mustards against V-79 Chinese hamster lung fibroblasts in vitro (IC50 = 1.8-69.1 muM). Several compounds showed excellent in vivo antitumor activity in CD2F1 mice against both P388/0 (Wild) and P388/CPA (CP-resistant) tumor cell lines.

  DOI：

  10.1021/jm0304764
• 作为产物：
  描述：

  N,N,N',N'-tetrakis(chloroethyl)chlorophosphorous diamide 在 叔丁基过氧化氢 、 三乙胺 作用下， 以 异辛烷 、 二氯甲烷 为溶剂， 反应 0.75h， 生成 N-[bis(2-chloroethyl)amino-[2-(4-nitrophenyl)sulfanylethoxy]phosphoryl]-2-chloro-N-(2-chloroethyl)ethanamine
  参考文献：
  名称：

  Sulfonyl-Containing Aldophosphamide Analogues as Novel Anticancer Prodrugs Targeted against Cyclophosphamide-Resistant Tumor Cell Lines

  摘要：

  A series of sulfonyl-group containing analogues of aldophosphamide (Aldo) were synthesized as potential anticancer prodrugs that liberate the cytotoxic phosphoramide mustards (PM, IPM, and tetrakis-PM) via beta-elimination, a nonenzymatic activation mechanism. Kinetic studies demonstrated that all these compounds spontaneously liberate phosphoramide mustards with half-lives in the range of 0.08-15.2 h under model physiological conditions in 0.08 M phosphate buffer at pH 7.4 and 37 degreesC. Analogous to Aldo, the rates of beta-elimination in all compounds was enhanced in reconstituted human plasma under same conditions. The compounds were more potent than the corresponding phosphoramide mustards against V-79 Chinese hamster lung fibroblasts in vitro (IC50 = 1.8-69.1 muM). Several compounds showed excellent in vivo antitumor activity in CD2F1 mice against both P388/0 (Wild) and P388/CPA (CP-resistant) tumor cell lines.

  DOI：

  10.1021/jm0304764