[Benzyl(2-chloroethylsulfamoyl)amino]methylbenzene | 182925-70-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [Benzyl(2-chloroethylsulfamoyl)amino]methylbenzene
• CAS: 182925-70-8
• 化学式: C₁₆H₁₉ClN₂O₂S
• 分子量: 338.858
• InChiKey: AETKNVWDDKSPNW-UHFFFAOYSA-N

物化性质

• 沸点：
  497.1±55.0 °C(Predicted)
• 密度：
  1.281±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [Benzyl(2-chloroethylsulfamoyl)amino]methylbenzene 在 甲酸 、 sodium nitrite 作用下， 反应 0.5h， 以84%的产率得到N-nitroso-N-(2-chloroethyl)-N’,N’-dibenzylsulfamide
  参考文献：
  名称：

  A new family of potential oncostatics: 2-chloroethylnitrososulfamides (CENS)—I. Synthesis, structure, and pharmacological evaluation (preliminary results)

  摘要：

  A new series of alkylating agents, 2-chloroethylnitrososulfamides (CENS), were developed on the model of 2-chloroethylnitrosoureas. Starting from chlorosulfonyl isocyanate, a four-step synthesis (carbamoylation-sulfamoylation, Mitsunobu alkylation, deprotection, and nitrosation) gives the title compounds in a 47-58% overall yield. The selection of the nitrosation site can be directed through an alternative route. The pharmacological evaluation shows a significant oncostatic activity towards both A549 and MCF7 cell lines. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00118-6
• 作为产物：
  描述：

  tert-butyl (2-chloroethyl)(N,N-dibenzylsulfamoyl)carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以95%的产率得到[Benzyl(2-chloroethylsulfamoyl)amino]methylbenzene
  参考文献：
  名称：

  A new family of potential oncostatics: 2-chloroethylnitrososulfamides (CENS)—I. Synthesis, structure, and pharmacological evaluation (preliminary results)

  摘要：

  A new series of alkylating agents, 2-chloroethylnitrososulfamides (CENS), were developed on the model of 2-chloroethylnitrosoureas. Starting from chlorosulfonyl isocyanate, a four-step synthesis (carbamoylation-sulfamoylation, Mitsunobu alkylation, deprotection, and nitrosation) gives the title compounds in a 47-58% overall yield. The selection of the nitrosation site can be directed through an alternative route. The pharmacological evaluation shows a significant oncostatic activity towards both A549 and MCF7 cell lines. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00118-6

文献信息

• Kinetic investigation on aqueous decomposition of 2-chloroethylnitrososulfamide
  作者：Achour Seridi、Mekki Kadri、Mohamed Abdaoui、Jean-Yves Winum、Jean-Louis Montero

  DOI：10.1016/j.bmcl.2005.10.080

  日期：2006.2

  2-chloroethylnitrososulfamides (CENS) was studied in aqueous buffered solutions with pH ranging from 0 to 14. The study was monitored by RP-LC-MS and conventional UV spectrophotometry. The reaction proceeded via a pseudo-first-order kinetic with significant correlation coefficient. The major decomposition products from CENS after incubation in phosphate buffer were isolated and identified by NMR and mass spectrometry

  在pH为0到14的缓冲水溶液中研究了2-氯乙基亚硝基磺酰胺（CENS）的动力学分解。该研究通过RP-LC-MS和常规UV分光光度法进行监测。该反应通过具有显着相关系数的拟一级动力学进行。在磷酸盐缓冲液中孵育后，CENS的主要分解产物被分离出来，并通过NMR和质谱鉴定。结果表明，该机理途径涉及CENS的脱氮和竞争性水解，其中亲核性攻击硫原子并形成氨基磺酸酯化合物。
• Study on the Decomposition of 2-Chloroethylnitro- sosulfamides (CENS) in Serum Using HPLC On-line Solid Phase Extraction
  作者：Achour Seridi、Jean-Yves Winum、Mekki Kadri、Mohamed Abdaoui、Jean-Louis Montero

  DOI：10.1002/ardp.200600071

  日期：2006.9

  investigated the kinetic decomposition of 2‐chloroethylnitrososulfamides (CENS) in fetal calf serum. The study was monitored by on‐line solid phase extraction linked to RP‐LC‐MS. We demonstrated that CENS are less stable in fetal calf serum than in aqueous buffer at pH 7.4 and 37°C. Moreover, we have shown that partition coefficient of CENS can be correlated to the kinetics decomposition, and we observe that

  在本文中，我们研究了胎牛血清中 2-氯乙基亚硝基磺酰胺 (CENS) 的动力学分解。该研究通过与 RP-LC-MS 相连的在线固相萃取进行监测。我们证明 CENS 在胎牛血清中的稳定性低于 pH 7.4 和 37°C 的水性缓冲液。此外，我们已经证明 CENS 的分配系数可以与动力学分解相关，并且我们观察到亲脂性 CENS 的稳定性更好。分解后的不同代谢物已通过 RP - HPLC - MS 初步鉴定。该研究表明，由比水性磷酸盐缓冲液更复杂的分解机制导致的几种代谢物的形成，产生了相同的主要产物。