N'-(2-chloro-ethyl)-N-(2-methanesulfonyloxy-ethyl)-N-methyl-phosphorodiamidic acid but-3-enyl ester | 60052-93-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N'-(2-chloro-ethyl)-N-(2-methanesulfonyloxy-ethyl)-N-methyl-phosphorodiamidic acid but-3-enyl ester
• CAS: 60052-93-9
• 化学式: C₁₀H₂₂ClN₂O₅PS
• 分子量: 348.788
• InChiKey: PEIYQRDKMUQIRO-UHFFFAOYSA-N

物化性质

• 沸点：
  465.5±55.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Predicted)

反应信息

• 作为反应物：
  描述：

  N'-(2-chloro-ethyl)-N-(2-methanesulfonyloxy-ethyl)-N-methyl-phosphorodiamidic acid but-3-enyl ester 生成 1-{[3-(2-chloro-ethyl)-4-hydroperoxy-2-oxo-2λ⁵-[1,3,2]oxazaphosphinan-2-yl]-methyl-amino}-2-methanesulfonyloxy-ethane
  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