tert-butyl N-hexylsulfamoylcarbamate | 182925-48-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 英文名称: tert-butyl N-hexylsulfamoylcarbamate
• 英文别名: tert-butyl N-(hexylsulfamoyl)carbamate
• CAS: 182925-48-0
• 化学式: C₁₁H₂₄N₂O₄S
• 分子量: 280.389
• InChiKey: OXPQTIQGXUSYJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  92.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl N-hexylsulfamoylcarbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以86%的产率得到N-(hexyl)sulfamide
  参考文献：
  名称：

  Synthesis of arabinose glycosyl sulfamides as potential inhibitors of mycobacterial cell wall biosynthesis

  摘要：

  A series of arabinose glycosyl sulfamides with varying alkyl chain types and lengths were synthesised as mimics of decaprenolphosphoarabinose (DPA), and as potential inhibitors of mycobacterial cell wall biosynthesis. Unprecedented conversion of the desired furanose to the thermodynamically more stable pyranose form occurred during final de-protection. Biological testing against Mycobacterium smegmatis revealed low to moderate anti-mycobacterial activity with marked dependence on alkyl chain length, which in the case of mono-substituted sulfamides was maximal for a C-10 chain. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.07.050
• 作为产物：
  描述：

  氯磺酰异氰酸酯 、 正己胺 、 叔丁醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.5h， 以80%的产率得到tert-butyl N-hexylsulfamoylcarbamate
  参考文献：
  名称：

  Synthesis of arabinose glycosyl sulfamides as potential inhibitors of mycobacterial cell wall biosynthesis

  摘要：

  A series of arabinose glycosyl sulfamides with varying alkyl chain types and lengths were synthesised as mimics of decaprenolphosphoarabinose (DPA), and as potential inhibitors of mycobacterial cell wall biosynthesis. Unprecedented conversion of the desired furanose to the thermodynamically more stable pyranose form occurred during final de-protection. Biological testing against Mycobacterium smegmatis revealed low to moderate anti-mycobacterial activity with marked dependence on alkyl chain length, which in the case of mono-substituted sulfamides was maximal for a C-10 chain. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.07.050

文献信息

• A new family of potential oncostatics: 2-chloroethylnitrososulfamides (CENS)—I. Synthesis, structure, and pharmacological evaluation (preliminary results)
  作者：Mohamed Abdaoui、Georges Dewynter、Nourredine Aouf、Gilles Favre、Alain Morère、Jean-Louis Montero

  DOI：10.1016/0968-0896(96)00118-6

  日期：1996.8

  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