N-(4-hydroxyphenyl)-4-(4-fluorophenyl)-1,3-thiazole-2-amine | 708998-00-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-hydroxyphenyl)-4-(4-fluorophenyl)-1,3-thiazole-2-amine
• 英文别名: 4-(4-(4-fluorphenyl)thiazol-2-ylamino)phenol；4-{[4-(4-Fluorophenyl)-1,3-thiazol-2-yl]amino}phenol；4-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]amino]phenol
• CAS: 708998-00-9
• 化学式: C₁₅H₁₁FN₂OS
• 分子量: 286.33
• InChiKey: IHEWKLRWCVXDOL-UHFFFAOYSA-N

物化性质

• 熔点：
  203 °C
• 沸点：
  481.8±55.0 °C(predicted)
• 密度：
  1.389±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-苯甲酰基-N'-(4-羟基苯基)硫脲 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 1.5h， 生成 N-(4-hydroxyphenyl)-4-(4-fluorophenyl)-1,3-thiazole-2-amine
  参考文献：
  名称：

  Multi-dimensional target profiling of N,4-diaryl-1,3-thiazole-2-amines as potent inhibitors of eicosanoid metabolism

  摘要：

  Eicosanoids like leukotrienes and prostaglandins play a considerable role in inflammation. Produced within the arachidonic acid (AA) cascade, these lipid mediators are involved in the pathogenesis of pain as well as acute and chronic inflammatory diseases like rheumatoid arthritis and asthma. With regard to the lipid cross-talk within the AA pathway, a promising approach for an effective anti-inflammatory therapy is the development of inhibitors targeting more than one enzyme of this cascade. Within this study, thirty N-4-diaryl-1,3-thiazole-2-amine based compounds with different substitution patterns were synthesized and tested in various cell-based assays to investigate their activity and selectivity profile concerning five key enzymes involved in eicosanoid metabolism (5-, 12-, 15-lipoxygenase (LO), cyclooxygenase-1 and -2 (COX-1/-2)). With compound 7, 2-(4-phenyl)thiazol-2-ylamino)phenol (ST-1355), a multi-target ligand targeting all tested enzymes is presented, whereas compound 9, 2-(4-(4-chlorophenyl)thiazol-2-ylamino)phenol (ST-1705), represents a potent and selective 5-LO and COX-2 inhibitor with an IC50 value of 0.9 ± 0.2 μM (5-LO) and a residual activity of 9.1 ± 1.1% at 10 μM (COX-2 product formation). The promising characteristics and the additional non-cytotoxic profile of both compounds reveal new lead structures for the treatment of eicosanoid-mediated diseases.

  DOI：

  10.1016/j.ejmech.2014.07.025

文献信息

• 一种抗菌增效剂及其制法和用途
  申请人：上海医药工业研究院

  公开号：CN107629022A

  公开（公告）日：2018-01-26

  本发明涉及一种抗菌增效剂及其制法和用途。具体地，本发明公开了式(I)所示的具有抗菌增效活性的化合物或其光学异构体、顺反异构体或医药学上可接受的盐，及其制备方法。本发明还公开了包含上述化合物的医用组合物及其用途。上述化合物可有效增强多粘菌素B对鲍曼不动杆菌与肺炎克雷伯菌的抗菌活性，并可应用于对多粘菌素不敏感或抑菌活性不强的病菌的抗菌治疗。
• Synthesis and Biological Evaluation of N-aryl-4-aryl-1,3-Thiazole-2-Amine Derivatives as Direct 5-Lipoxygenase Inhibitors
  作者：Jeehee Suh、Eul Kgun Yum、Hyae Gyeong Cheon、Young Sik Cho

  DOI：10.1111/j.1747-0285.2012.01371.x

  日期：2012.7

  Biological evaluation of N‐aryl‐4‐aryl‐1,3‐thiazole‐2‐amine derivatives was examined for anti‐inflammatory activity in in vitro and in vivo assays. The thiazole compounds showed direct inhibition of 5‐lipoxygenase (LOX) that is a key enzyme of leukotrienes synthesis and involved in the inflammation‐related diseases, including asthma and rheumatoid arthritis. To optimize biological activity, we synthesized 1

  在体外和体内试验中，对N-芳基-4-芳基-1,3-噻唑-2-胺衍生物进行了生物学评估，以评估其抗炎活性。噻唑化合物显示出对5-脂氧合酶（LOX）的直接抑制，这是白三烯合成的关键酶，并参与炎症相关疾病，包括哮喘和类风湿关节炎。为了优化生物活性，我们合成了1,3-噻唑-2-胺衍生物，并研究了结构和活性之间的关系。尤其是，N-（3,5-二甲基苯基）-4-（4-氯苯基）-1,3-噻唑-2-胺被证明具有有效的抗炎活性，可作为5-LOX抑制剂。