2-(2-chloro-ethylamino)-3-(2-methanesulfonyloxy-ethyl)-2-oxo-2λ⁵-[1,3,2]oxazaphosphinan-4-one | 65174-61-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 2-(2-chloro-ethylamino)-3-(2-methanesulfonyloxy-ethyl)-2-oxo-2λ⁵-[1,3,2]oxazaphosphinan-4-one
• CAS: 65174-61-0
• 化学式: C₈H₁₆ClN₂O₆PS
• 分子量: 334.718
• InChiKey: VXDRSSBDSHPVBC-UHFFFAOYSA-N

物化性质

• 沸点：
  497.0±55.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.15
• 重原子数：
  19.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  102.01
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  N-(2-chloro-ethyl)-N'-(2-methanesulfonyloxy-ethyl)-phosphorodiamidic acid but-3-enyl ester 在 iron(II) sulfate 作用下， 以 氯仿 为溶剂， 反应 7.0h， 生成 2-(2-chloro-ethylamino)-3-(2-methanesulfonyloxy-ethyl)-2-oxo-2λ⁵-[1,3,2]oxazaphosphinan-4-one
  参考文献：
  名称：

  Studies on cyclophosphamide metabolites and their related compounds. 8. Synthesis and antitumor activity of preactivated isophosphamide analogs bearing modified alkylating functionalities

  摘要：

  In search of cancer chemotherapeutic agents with greater efficacy than cyclophosphamide, 4-hydroperoxyisophosphamide analogues bearing modified alkylating functionalities such as 2-bromoethyl, 2-iodoethyl, 2-methyl-sulfonyloxyethyl, and 2-ethylsulfonyloxyethyl groups were prepared by ozonolytic cyclization reaction of N,N'-substituted 3-butenyl phosphorodiamidates. Comparative cytotoxicity against L1210 cells and antileukemic life-span activity against L1210 implanted BDF1 mice of the newly synthesized compounds were tabulated. The 4-hydroperoxyisophosphamide analogues which have different alkylating groups in a molecule showed slightly greater cytoxicity in vitro than those with the same alkylating groups. Most of the compounds having different alkylating groups also showed high antileukemic activity in vivo. Among them, the highest efficacy was found for 2-[N-methyl-n-(2-chlorethyl)]amino-3-(2-methylsulfonyloxyethyl)-4-hydroperoxy-1,3,2-oxazaphosphorinane 2-xoide (NSC 280122D) whos life-span activity was also greater than that of 4-hydroperoxyisophosphamide, cyclophosphamide, and isoposphamide. The superiority of this compound was especially apparent by oral administration.

  DOI：

  10.1021/jm00200a013