N-[4-[2-[4-[(N'-propan-2-ylcarbamimidoyl)amino]phenyl]ethyl]-1,3-thiazol-2-yl]acetamide | 1426055-69-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-[4-[2-[4-[(N'-propan-2-ylcarbamimidoyl)amino]phenyl]ethyl]-1,3-thiazol-2-yl]acetamide
• CAS: 1426055-69-7
• 化学式: C₁₇H₂₃N₅OS
• 分子量: 345.469
• InChiKey: MAGISGXUSXDIJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-{4-[(Z)-2-(4-nitrophenyl)ethenyl]-1,3-thiazol-2-yl}acetamide 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 丙酮 为溶剂， 20.0~60.0 ℃ 、405.33 kPa 条件下， 反应 28.0h， 生成 N-[4-[2-[4-[(N'-propan-2-ylcarbamimidoyl)amino]phenyl]ethyl]-1,3-thiazol-2-yl]acetamide
  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.