(E)-4-(3,5-Dimethoxyphenyl)-1-(4,5,6,7-tetrahydrobenzo[d]thiazol-2-ylamino)but-3-en-2-one | 1107621-06-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-4-(3,5-Dimethoxyphenyl)-1-(4,5,6,7-tetrahydrobenzo[d]thiazol-2-ylamino)but-3-en-2-one
• 英文别名: (E)-3-(3,5-dimethoxyphenyl)-N-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)prop-2-enamide
• CAS: 1107621-06-6
• 化学式: C₁₈H₂₀N₂O₃S
• 分子量: 344.434
• InChiKey: FUNCDLLJRBQKKA-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  88.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4,5,6,7-四氢苯并噻唑-2-胺 、 3,5-dimethoxycinnamoyl chloride 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以40%的产率得到(E)-4-(3,5-Dimethoxyphenyl)-1-(4,5,6,7-tetrahydrobenzo[d]thiazol-2-ylamino)but-3-en-2-one
  参考文献：
  名称：

  Design, Synthesis, and Cytoprotective Effect of 2-Aminothiazole Analogues as Potent Poly(ADP-Ribose) Polymerase-1 Inhibitors

  摘要：

  A series of novel poly(ADP-ribose) polymerase-1 (PARP-1) inhibitors were designed within 2-aminothiazole analogues (4-10) based on a constructed three-dimensional pharmacophore model. After synthesis, the inhibitory effect on PARP-1 activity and the cytoprotective action of these compounds were tested and evaluated. Among them, compounds 4-6 and 10 appeared to be potent PARP-1 inhibitors with IC50 values less than 1 mu M, which had been perfectly predicted by pharmacophore model. These compounds proved to be highly potent against cell injury induced by H2O2 and oxygen-glucose deprivation (OGD) in PC12 cells. These novel 2-aminothiazole analogues are potentially applicable as neuroprotective agents for the treatment of neurological diseases.

  DOI：

  10.1021/jm800902t

文献信息

• Design, Synthesis, and Cytoprotective Effect of 2-Aminothiazole Analogues as Potent Poly(ADP-Ribose) Polymerase-1 Inhibitors
  作者：Wen-Ting Zhang、Jin-Lan Ruan、Peng-Fei Wu、Feng-Chao Jiang、Li−Na Zhang、Wei Fang、Xiang-Long Chen、Yue Wang、Bao-Shuai Cao、Gang-Ying Chen、Yi-Jing Zhu、Jun Gu、Jian-Guo Chen

  DOI：10.1021/jm800902t

  日期：2009.2.12

  A series of novel poly(ADP-ribose) polymerase-1 (PARP-1) inhibitors were designed within 2-aminothiazole analogues (4-10) based on a constructed three-dimensional pharmacophore model. After synthesis, the inhibitory effect on PARP-1 activity and the cytoprotective action of these compounds were tested and evaluated. Among them, compounds 4-6 and 10 appeared to be potent PARP-1 inhibitors with IC50 values less than 1 mu M, which had been perfectly predicted by pharmacophore model. These compounds proved to be highly potent against cell injury induced by H2O2 and oxygen-glucose deprivation (OGD) in PC12 cells. These novel 2-aminothiazole analogues are potentially applicable as neuroprotective agents for the treatment of neurological diseases.