N-{4-[2-(4-nitrophenyl)vinyl]phenyl}acetamide | 15427-50-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: N-{4-[2-(4-nitrophenyl)vinyl]phenyl}acetamide
• 英文别名: 4-Acetamino-4'-nitro-stilben；N-[4-[(E)-2-(4-nitrophenyl)ethenyl]phenyl]acetamide；N-[4-[2-(4-nitrophenyl)ethenyl]phenyl]acetamide
• CAS: 15427-50-6
• 化学式: C₁₆H₁₄N₂O₃
• 分子量: 282.299
• InChiKey: KMYUHKCVKYYXKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-{4-[2-(4-nitrophenyl)vinyl]phenyl}acetamide 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~60.0 ℃ 、303.99 kPa 条件下， 反应 25.0h， 生成 N-[4-[2-[4-(diaminomethylideneamino)phenyl]ethyl]phenyl]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

  摘要：

  Vascular adhesion protein-1 (VAP-1), an amine oxidase that is also known as a semicarbazide-sensitive amine oxidase (SSAO), is present in particularly high levels in human plasma, and is considered a potential therapeutic target for various inflammatory diseases, including diabetes complications such as macular edema.In our VAP-1 inhibitor program, structural modifications following high-throughput screening (HTS) of our compound library resulted in the discovery that thiazole derivative 10, which includes a guanidine group, shows potent human VAP-1 inhibitory activity (IC50 of 230 nM; rat IC50 of 14 nM). Moreover, compound 10 exhibited significant inhibitory effects on ocular permeability in STZ-induced diabetic rats. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.12.025

文献信息

• Synthesis and SAR study of new thiazole derivatives as vascular adhesion protein-1 (VAP-1) inhibitors for the treatment of diabetic macular edema
  作者：Takayuki Inoue、Masataka Morita、Takashi Tojo、Kousei Yoshihara、Akira Nagashima、Ayako Moritomo、Mitsuru Ohkubo、Hiroshi Miyake

  DOI：10.1016/j.bmc.2012.12.025

  日期：2013.3

  Vascular adhesion protein-1 (VAP-1), an amine oxidase that is also known as a semicarbazide-sensitive amine oxidase (SSAO), is present in particularly high levels in human plasma, and is considered a potential therapeutic target for various inflammatory diseases, including diabetes complications such as macular edema.In our VAP-1 inhibitor program, structural modifications following high-throughput screening (HTS) of our compound library resulted in the discovery that thiazole derivative 10, which includes a guanidine group, shows potent human VAP-1 inhibitory activity (IC50 of 230 nM; rat IC50 of 14 nM). Moreover, compound 10 exhibited significant inhibitory effects on ocular permeability in STZ-induced diabetic rats. (C) 2013 Elsevier Ltd. All rights reserved.