2-[2-(bis-(2-chloroethyl)-amino)-2-oxo-tetrahydro-2H-1,3,2-oxazaphosphorin-4-yl-thio]-ethanesulphonic acid cyclohexylammonium salt | 99280-05-4

• 英文名称: 2-[2-(bis-(2-chloroethyl)-amino)-2-oxo-tetrahydro-2H-1,3,2-oxazaphosphorin-4-yl-thio]-ethanesulphonic acid cyclohexylammonium salt
• 英文别名: ASTA-Z-7654(free acid)；2-[[2-[bis(2-chloroethyl)amino]-2-oxo-1,3,2λ5-oxazaphosphinan-4-yl]sulfanyl]ethanesulfonate;cyclohexylazanium
• CAS: 99280-05-4
• 化学式: C₆H₁₃N*C₉H₁₉Cl₂N₂O₅PS₂
• 分子量: 500.448
• InChiKey: AJOJXYODECALSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  156
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-[2-(bis-(2-chloroethyl)-amino)-2-oxo-tetrahydro-2H-1,3,2-oxazaphosphorin-4-yl-thio]-ethanesulphonic acid cyclohexylammonium salt 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 4-methoxycyclophosphamide
  参考文献：
  名称：

  Spectroscopic detection of iminocyclophosphamide and its possible role in cyclophosphamide metabolism

  摘要：

  Iminocyclophosphamide (4) has been identified by 1H NMR as a product from base treatment of 4-alkylthio-substituted cyclophosphamide derivatives, viz., cis-4-(propylthio)cyclophosphamide (cis-7). A maximum concentration of approximately 12% of total product was observed by treating cis-7 with ethyl propiolate and NaH or deuteriated dimsyl anion in anhydrous Me2SO-d6. Treatment of cis-7 with base alone established a rapid cis-/trans-7 equilibrium via the imine intermediate 4. Base-catalyzed expulsion of 1-propanethiol (8) from cis-7 and thiol trapping afforded formation of 4, which subsequently underwent elimination to the relatively more stable conjugated (vinylimino)-phosphamide (9). Iminocyclophosphamide (4) was also identified by fast atom bombardment mass spectrometry as a product generated upon analysis of cyclophosphamide derivatives substituted in the 4-position of the oxazaphosphorine ring with various leaving groups.

  DOI：

  10.1021/jm00389a024
• 作为产物：
  描述：

  4-methoxycyclophosphamide 、 cyclohexylammonium-2-mercaptoethanesulphonate 在 三氯乙酸 作用下， 以 N-甲基乙酰胺 为溶剂， 以94%的产率得到2-[2-(bis-(2-chloroethyl)-amino)-2-oxo-tetrahydro-2H-1,3,2-oxazaphosphorin-4-yl-thio]-ethanesulphonic acid cyclohexylammonium salt
  参考文献：
  名称：

  Oxazaphosphorin-4-thio-alkanesulphonic acids, and neutral salts thereof

  摘要：

  本发明涉及新的氧杂磷四硫代烷磺酸和相应的中性盐，其化学式为I，用于控制癌症疾病和在人类和动物中产生免疫抑制的方法。

  公开号：

  US04623742A1

文献信息

• oxazaphosphorin-4-thio alkanesulphonic acids, neutral salts thereof and
  申请人：ASTA Pharma Aktiengesellshaft

  公开号：US04929607A1

  公开（公告）日：1990-05-29

  This invention relates to new oxzaphosphorin-4-thio-alkanesulphonic acids and to the neutral salts thereof corresponding to the general formula I ##STR1## and to methods to use such compounds to treat cancer diseases and to produce immunosuppression in humans and animals.

  本发明涉及新的氧杂磷环四硫代烷磺酸及其相应的中性盐，其化学式为I式：##STR1##以及使用这些化合物治疗癌症和在人类和动物中产生免疫抑制的方法。
• US4623742A
  申请人：——

  公开号：US4623742A

  公开（公告）日：1986-11-18
• US4929607A
  申请人：——

  公开号：US4929607A

  公开（公告）日：1990-05-29