tert-butyl {(Z)-{[4-(2-{3-acetamido-5-[4-(methylsulfonyl)phenyl]-1H-pyrazol-1-yl}ethyl)phenyl]amino}-[(tert-butoxycarbonyl)amino]methylene}carbamate | 1429659-53-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: tert-butyl {(Z)-{[4-(2-{3-acetamido-5-[4-(methylsulfonyl)phenyl]-1H-pyrazol-1-yl}ethyl)phenyl]amino}-[(tert-butoxycarbonyl)amino]methylene}carbamate
• CAS: 1429659-53-9
• 化学式: C₃₁H₄₀N₆O₇S
• 分子量: 640.761
• InChiKey: MSIPCXQHNRCYJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.38
• 重原子数：
  45.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  170.08
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  tert-butyl {(Z)-{[4-(2-{3-acetamido-5-[4-(methylsulfonyl)phenyl]-1H-pyrazol-1-yl}ethyl)phenyl]amino}-[(tert-butoxycarbonyl)amino]methylene}carbamate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 7.0h， 以98%的产率得到N-[1-[2-[4-(diaminomethylideneamino)phenyl]ethyl]-5-(4-methylsulfonylphenyl)pyrazol-3-yl]acetamide;hydrochloride
  参考文献：
  名称：

  Synthesis and SAR study of new thiazole derivatives as vascular adhesion protein-1 (VAP-1) inhibitors for the treatment of diabetic macular edema: Part 2

  摘要：

  Novel thiazole derivatives were synthesized and evaluated as vascular adhesion protein-1 (VAP-1) inhibitors. Although our previous compound 1 showed potent VAP-1 inhibitory activity, the activity differed between humans and rats. This issue was overcome by a hybrid design using human VAP-1 specific inhibitor 2, which was found by high-throughput screening (HTS), a docking study of a human VAP-1 homology model, and an analysis of sequence information for humans and rats. As a result, we identified compound 35c, which showed strong VAP-1 inhibitory activity (human IC50 of 20 nM; rat IC50 of 72 nM) and significant inhibitory effects in the ex vivo test. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.048
• 作为产物：
  描述：

  3-(4-(methylthio)phenyl)-3-oxopropanenitrile 在 吡啶 、 盐酸 、 potassium carbonate 、 一水合肼 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 89.0h， 生成 tert-butyl {(Z)-{[4-(2-{3-acetamido-5-[4-(methylsulfonyl)phenyl]-1H-pyrazol-1-yl}ethyl)phenyl]amino}-[(tert-butoxycarbonyl)amino]methylene}carbamate
  参考文献：
  名称：

  Synthesis and SAR study of new thiazole derivatives as vascular adhesion protein-1 (VAP-1) inhibitors for the treatment of diabetic macular edema: Part 2

  摘要：

  Novel thiazole derivatives were synthesized and evaluated as vascular adhesion protein-1 (VAP-1) inhibitors. Although our previous compound 1 showed potent VAP-1 inhibitory activity, the activity differed between humans and rats. This issue was overcome by a hybrid design using human VAP-1 specific inhibitor 2, which was found by high-throughput screening (HTS), a docking study of a human VAP-1 homology model, and an analysis of sequence information for humans and rats. As a result, we identified compound 35c, which showed strong VAP-1 inhibitory activity (human IC50 of 20 nM; rat IC50 of 72 nM) and significant inhibitory effects in the ex vivo test. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.048