(E)-N-((1H-indol-3-yl)methylene)-4-(2,4-diethoxyphenyl)thiazol-2-amine | 1107621-07-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (E)-N-((1H-indol-3-yl)methylene)-4-(2,4-diethoxyphenyl)thiazol-2-amine
• 英文别名: (E)-N-((1H-Indol-3-yl)methylene)-4-(2,4-diethoxyphenyl)thiazol-2-amine；(E)-N-[4-(2,4-diethoxyphenyl)-1,3-thiazol-2-yl]-1-(1H-indol-3-yl)methanimine
• CAS: 1107621-07-7
• 化学式: C₂₂H₂₁N₃O₂S
• 分子量: 391.494
• InChiKey: BQOKRGNGLBKKAI-ZMOGYAJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  87.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-吲哚甲醛 、 4-(2,4-diethoxy-phenyl)-2-aminothiazole 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 1.02h， 以94%的产率得到(E)-N-((1H-indol-3-yl)methylene)-4-(2,4-diethoxyphenyl)thiazol-2-amine
  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

• 2-AMINOTHIAZOLE DERIVATIVE, PREPARATION METHOD, AND USE
  申请人：Huazhong University of Science and Technology

  公开号：EP2682390A1

  公开（公告）日：2014-01-08

  The present invention relates to the preparation of a 2-aminothiazole derivative having a structure as formula (I) and a therapeutic effect thereof for Alzheimer's disease (AD), and a therapeutic effect thereof against transplant rejection, autoimmune diseases, ischemia-reperfusion injury, chronic inflammation response, endotoxemia, and other diseases.

  本发明涉及制备具有如下式（I）结构的2-氨基噻唑衍生物及其对阿尔茨海默病（AD）的治疗效果，以及其对移植排斥、自身免疫疾病、缺血再灌注损伤、慢性炎症反应、内毒素血症和其他疾病的治疗效果。
• 2-AMINOTHIAZOLE DERIVATIVES AND METHODS OF PREPARING AND USING THE SAME
  申请人：Hangzhou Zhongmei Huadong Pharmaceutical Co., Ltd.

  公开号：US20140004155A1

  公开（公告）日：2014-01-02

  2-aminothiazole derivatives represented by formula (I), where R 1 and R 2 represent cycloalkyls, respectively; or R 1 represents a substituted aromatic group, and R 2 represents H, a C 1 -C 11 alkyl, —CH 2 Ph (benzyl), or a methyl ether including a C 1 -C 11 alkyl. R 3 is a substituent including an amino group. X represents a carbonyl or a methylene and n is an integer from 0 to 5.

  公式（I）代表的2-氨基噻唑衍生物，其中R1和R2分别代表环烷基；或者R1代表一个取代的芳香基团，R2代表H，一个C1-C11烷基，—CH2Ph（苄基），或者包括一个C1-C11烷基的甲基醚。R3是一个包含氨基的取代基。X代表一个羰基或一个亚甲基，n是一个从0到5的整数。
• 2-AMINOTHIAZOLE DERIVATIVES FOR MEDICAL USE
  申请人：Huazhong University of Science and Technology

  公开号：EP3424912A1

  公开（公告）日：2019-01-09

  The present invention relates to the preparation of a 2-aminothiazole derivative having a structure as formula (I) and a therapeutic effect thereof for Alzheimer's disease (AD), and a therapeutic effect thereof against transplant rejection, autoimmune diseases, ischemia-reperfusion injury, chronic inflammation response, endotoxemia, and other diseases.

  本发明涉及一种具有式（I）结构的 2-氨基噻唑衍生物的制备及其对阿尔茨海默病（AD）的治疗效果，以及其对移植排斥、自身免疫性疾病、缺血再灌注损伤、慢性炎症反应、内毒素血症和其他疾病的治疗效果。
• US9771340B2
  申请人：——

  公开号：US9771340B2

  公开（公告）日：2017-09-26
• 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.