2,6-dimethyl-3-heptanone O-[amino(bis(2-chloroethyl)amino)phosphinyl]oxime | 87040-48-0

• 英文名称: 2,6-dimethyl-3-heptanone O-[amino(bis(2-chloroethyl)amino)phosphinyl]oxime
• 英文别名: N-[amino-(2,6-dimethylheptan-4-ylideneamino)oxyphosphoryl]-2-chloro-N-(2-chloroethyl)ethanamine
• CAS: 87040-48-0
• 化学式: C₁₃H₂₈Cl₂N₃O₂P
• 分子量: 360.264
• InChiKey: MHXLVAYPCGUDHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  67.92
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  双(2-氯乙基)氨基磷酰二氯 、 2,6-dimethyl-4-heptanone oxime 在 氨 、 三乙胺 作用下， 生成 2,6-dimethyl-3-heptanone O-[amino(bis(2-chloroethyl)amino)phosphinyl]oxime
  参考文献：
  名称：

  O-Imino esters of N,N-bis(2-chloroethyl)phosphorodiamidic acid. Synthesis, x-ray structure determination, and anticancer evaluation

  摘要：

  Nine representatives of the title series of compounds [(ClCH2CH2)2NP(O)(NH2)ON = CRR'] were synthesized as potential anticancer prodrugs, based on the possibility of enzymatic reduction of the N-O bond to release the known cytotoxic agent phosphoramide mustard [1, (ClCH2CH2)2NP(O)(NH2)OH]. The dimethyl derivative (2, R = R' = CH3) exhibited a statistically significant, albeit low, level of anti-L1210 activity in mice. Derivative 2, which was shown by 31P NMR measurements to be very stable toward hydrolysis at 37 degrees C over a pH range of 5.7-7.4 (T1/2 congruent to 7-8 weeks), gave colorimetrically detectable amounts of alkylating material upon incubation with mouse liver slices: approximately 3-5% conversion after 20 min at 37 degrees C. A single-crystal X-ray study of 2 revealed an unusual hydrogen-bonded "ladder" and a very similar steric relationship for the NCH2CH2Cl and ON = CCH3 moieties.

  DOI：

  10.1021/jm00366a029