2-[N¹-(pentafluorophenoxycarbonyl)-N²-(tert-butoxycarbonyl)hydrazino]ethyl methyl sulfone | 255873-71-3

• 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: 2-[N¹-(pentafluorophenoxycarbonyl)-N²-(tert-butoxycarbonyl)hydrazino]ethyl methyl sulfone
• 英文别名: (2,3,4,5,6-pentafluorophenyl) N-[(2-methylpropan-2-yl)oxycarbonylamino]-N-(2-methylsulfonylethyl)carbamate
• CAS: 255873-71-3
• 化学式: C₁₅H₁₇F₅N₂O₆S
• 分子量: 448.368
• InChiKey: LDHDBFBWZJMAAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-[N¹-(pentafluorophenoxycarbonyl)-N²-(tert-butoxycarbonyl)hydrazino]ethyl methyl sulfone 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 一水合肼 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 azo-N¹-(phenethylformamide)-N^1'-[2-(N²-tert-butoxycarbonyl)hydrazino]ethyl methyl sulfone formamide
  参考文献：
  名称：

  Azodicarboxamides:  A New Class of Cysteine Proteinase Inhibitor for Hepatitis A Virus and Human Rhinovirus 3C Enzymes

  摘要：

  Hepatitis A virus (HAV) 3C and human rhinovirus (HRV) 3C cysteine proteinases have been shown to be essential for viral maturation and infectivity through the cleavage of a viral polyprotein precursor. A number of bis-hydrazides (e.g., 11-14), analogous to nanomolar inhibitors of cathepsin K, were synthesized and tested for effectiveness against HAV 3C and HRV 3C proteinases, but these compounds showed no significant inhibition of the viral enzymes. However, oxidation of the bis-hydrazides to the corresponding azodicarboxamides gave potent, irreversible inhibitors with IC50's in the low micromolar range. These compounds probably act. by adding the active site thiol to the azo moiety in a Michael fashion to give a covalent complex, which was detected by electrospray mass spectrometry. Azodicarboxamide 16 was shown to have a rate constant (k(inact)/k(I)) of 35 644 M-1 min(-1).

  DOI：

  10.1021/jo9915123
• 作为产物：
  描述：

  2-[N¹-(carbobenzyloxy)-N²-(carbobenzyloxy)-N²-(tert-butoxycarbonyl)hydrazino]ethyl methyl sulfone 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.33h， 生成 2-[N¹-(pentafluorophenoxycarbonyl)-N²-(tert-butoxycarbonyl)hydrazino]ethyl methyl sulfone
  参考文献：
  名称：

  Azodicarboxamides:  A New Class of Cysteine Proteinase Inhibitor for Hepatitis A Virus and Human Rhinovirus 3C Enzymes

  摘要：

  Hepatitis A virus (HAV) 3C and human rhinovirus (HRV) 3C cysteine proteinases have been shown to be essential for viral maturation and infectivity through the cleavage of a viral polyprotein precursor. A number of bis-hydrazides (e.g., 11-14), analogous to nanomolar inhibitors of cathepsin K, were synthesized and tested for effectiveness against HAV 3C and HRV 3C proteinases, but these compounds showed no significant inhibition of the viral enzymes. However, oxidation of the bis-hydrazides to the corresponding azodicarboxamides gave potent, irreversible inhibitors with IC50's in the low micromolar range. These compounds probably act. by adding the active site thiol to the azo moiety in a Michael fashion to give a covalent complex, which was detected by electrospray mass spectrometry. Azodicarboxamide 16 was shown to have a rate constant (k(inact)/k(I)) of 35 644 M-1 min(-1).

  DOI：

  10.1021/jo9915123