3,3-diacetoxypropyl N,N-bis(2-chloroethyl)phosphorodiamidate | 113341-60-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3,3-diacetoxypropyl N,N-bis(2-chloroethyl)phosphorodiamidate
• 英文别名: Acetaldophosphamide；[1-acetyloxy-3-[amino-[bis(2-chloroethyl)amino]phosphoryl]oxypropyl] acetate
• CAS: 113341-60-9
• 化学式: C₁₁H₂₁Cl₂N₂O₆P
• 分子量: 379.177
• InChiKey: QSXPVYOILSESJY-UHFFFAOYSA-N

物化性质

• 熔点：
  51 °C(Solv: ethyl ether (60-29-7); acetone (67-64-1))
• 沸点：
  490.9±55.0 °C(Predicted)
• 密度：
  1.346±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  22
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,3-diacetoxypropyl N,N-bis(2-chloroethyl)phosphorodiamidate 在 phosphate buffer 作用下， 生成 磷酰胺氮芥 、 丙烯醛
  参考文献：
  名称：

  Aldophosphamide acetal diacetate and structural analogs: synthesis and cytotoxicity studies

  摘要：

  The synthesis of aldophosphamide acetal diacetate and a number of structural analogues is described. These compounds are designed to undergo biotransformation to the corresponding aldehydes in the presence of carboxylate esterases, enzymes that are ubiquitous in mammalian tissue. Several of these aldehydes can theoretically exist in pseudoequilibrium with the 4-hydroxyoxazaphosphorine tautomers; others lack this capability. The half-lives of the acetals in 0.05 M phosphate buffer, pH 7.4, at 37-degrees-C ranged from 1 to 2 days. In the presence of 2 unit equiv of porcine liver carboxylate esterase, all of the compounds were hydrolyzed with half-lives of less than 1 min. Although closely structurally related, the compounds exhibited a wide range of cytotoxicities to L1210 murine leukemia cells in vitro.

  DOI：

  10.1021/jm00105a030
• 作为产物：
  描述：

  3,3-diacetoxypropyl N,N-bis(2-chloroethyl)phosphoramidochloridate 在 ammonium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以71%的产率得到3,3-diacetoxypropyl N,N-bis(2-chloroethyl)phosphorodiamidate
  参考文献：
  名称：

  Aldophosphamide acetal diacetate and structural analogs: synthesis and cytotoxicity studies

  摘要：

  The synthesis of aldophosphamide acetal diacetate and a number of structural analogues is described. These compounds are designed to undergo biotransformation to the corresponding aldehydes in the presence of carboxylate esterases, enzymes that are ubiquitous in mammalian tissue. Several of these aldehydes can theoretically exist in pseudoequilibrium with the 4-hydroxyoxazaphosphorine tautomers; others lack this capability. The half-lives of the acetals in 0.05 M phosphate buffer, pH 7.4, at 37-degrees-C ranged from 1 to 2 days. In the presence of 2 unit equiv of porcine liver carboxylate esterase, all of the compounds were hydrolyzed with half-lives of less than 1 min. Although closely structurally related, the compounds exhibited a wide range of cytotoxicities to L1210 murine leukemia cells in vitro.

  DOI：

  10.1021/jm00105a030

文献信息

• FARQUHAR, DAVID;WANG, YUQIANG
  作者：FARQUHAR, DAVID、WANG, YUQIANG

  DOI：——

  日期：——
• WANG, YUQIANG;FARQUHAR, DAVID, J. MED. CHEM., 34,(1991) N, C. 197-203
  作者：WANG, YUQIANG、FARQUHAR, DAVID

  DOI：——

  日期：——
• Aldophosphamide acetal diacetate and structural analogs: synthesis and cytotoxicity studies
  作者：Yuqiang Wang、David Farquhar

  DOI：10.1021/jm00105a030

  日期：1991.1

  The synthesis of aldophosphamide acetal diacetate and a number of structural analogues is described. These compounds are designed to undergo biotransformation to the corresponding aldehydes in the presence of carboxylate esterases, enzymes that are ubiquitous in mammalian tissue. Several of these aldehydes can theoretically exist in pseudoequilibrium with the 4-hydroxyoxazaphosphorine tautomers; others lack this capability. The half-lives of the acetals in 0.05 M phosphate buffer, pH 7.4, at 37-degrees-C ranged from 1 to 2 days. In the presence of 2 unit equiv of porcine liver carboxylate esterase, all of the compounds were hydrolyzed with half-lives of less than 1 min. Although closely structurally related, the compounds exhibited a wide range of cytotoxicities to L1210 murine leukemia cells in vitro.