4-((4-phenylthiazol-2-yl)amino)phenol | 3394-73-8

• 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: 4-((4-phenylthiazol-2-yl)amino)phenol
• 英文别名: 4-(4-Phenylthiazol-2-ylamino)phenol；4-[(4-phenyl-1,3-thiazol-2-yl)amino]phenol
• CAS: 3394-73-8
• 化学式: C₁₅H₁₂N₂OS
• 分子量: 268.339
• InChiKey: DERMXGZWGLKTNH-UHFFFAOYSA-N

物化性质

• 熔点：
  203 °C
• 沸点：
  485.0±47.0 °C(Predicted)
• 密度：
  1.329±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 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：
  4

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 4-((4-phenylthiazol-2-yl)amino)phenol
  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。
• Thiocyanation and 2-Amino-1,3-thiazole Formation in Water Using Recoverable and Reusable Glycosylated Resorcin[4]arene Cavitands
  作者：Ali A. Husain、Kirpal S. Bisht

  DOI：10.1021/acs.joc.0c01150

  日期：2020.8.7

  resorcin[4]arene cavitand glycoconjugates (RCGs) have been applied as efficient recoverable and reusable inverse phase transfer catalysts for eco- and environmentally friendly thiocyanation and 2-amino-1,3-thiazole formation reactions in water. The results show that RCGs (1 mol %) were capable of hosting and catalyzing various water-insoluble bromo/thiocyanato substrates in water without the use of any co-organic

  三种空间定向间苯二酚[4]芳烃cavitand糖共轭物（RCGs）系列已被用作高效可回收和可重复使用的反相转移催化剂，用于生态和环境友好的硫氰化和2-氨基-1,3-噻唑在水中的形成反应。结果表明，在不使用任何共有机溶剂的情况下，RCG（1摩尔％）能够在水中容纳和催化各种水不溶性溴/硫氰酸根基质。在使用DCM或乙酸乙酯对所需产物进行简单萃取后，再对回收的含有HCG催化剂的水溶液进行处理，还检查了RCG催化体系RCG1和RCG3的可回收性和可重复使用性。RCG催化剂进入下一个反应周期。
• COMPOSITIONS AND METHODS RELATING TO HEAT SHOCK TRANSCRIPTION FACTOR ACTIVATING COMPOUNDS AND TARGETS THEREOF
  申请人：Thiele Dennis J.

  公开号：US20110112073A1

  公开（公告）日：2011-05-12

  The present invention relates to HSF activating compounds, methods for their discovery, and their research and therapeutic uses, as well as pharmaceutically acceptable salts, solvates, chelates, non-covalent complexes, prodrugs, mixtures (including both R and S enantiomeric forms and racemic mixtures thereof), and pharmaceutical Formulations thereof. In particular, the present invention provides compounds capable of facilitating HSF1 homotrimerization, and methods of using such compounds as therapeutic agents to treat a number of conditions associated with irregular HSF1 activity.

  本发明涉及HSF激活化合物，其发现方法，以及其研究和治疗用途，以及药学上可接受的盐类、溶剂化合物、螯合物、非共价络合物、前药、混合物（包括R和S对映体形式和它们的消旋混合物），以及其药物配方。具体而言，本发明提供了能够促进HSF1同聚三聚体化的化合物，以及使用这些化合物作为治疗剂治疗与异常HSF1活性相关的多种疾病的方法。
• SUBSTITUTED PYRAZOLES AS HEAT SHOCK TRANSCRIPTION FACTOR ACTIVATORS
  申请人：DUKE UNIVERSITY

  公开号：US20160221958A1

  公开（公告）日：2016-08-04

  The present invention relates to HSF activating compounds, methods for their discovery, and their research and therapeutic uses, as well as pharmaceutically acceptable salts, solvates, chelates, non-covalent complexes, prodrugs, mixtures (including both R and S enantiomeric forms and racemic mixtures thereof), and pharmaceutical Formulations thereof. In particular, the present invention provides compounds capable of facilitating HSF1 homotrimerization, and methods of using such compounds as therapeutic agents to treat a number of conditions associated with irregular HSF1 activity.

  本发明涉及HSF激活化合物，其发现方法以及它们的研究和治疗用途，以及其药学上可接受的盐，溶剂化物，螯合物，非共价复合物，前药，混合物（包括R和S对映体形式和它们的混合物），以及其制剂。特别是，本发明提供了能够促进HSF1同源三聚体形成的化合物，以及使用这些化合物作为治疗剂治疗与不规则HSF1活性相关的多种疾病的方法。
• Synthesis of a Thiazole Library via an Iridium-Catalyzed Sulfur Ylide Insertion Reaction
  作者：Storm Hassell-Hart、Elisa Speranzini、Sirihathai Srikwanjai、Euan Hossack、S. Mark Roe、Daren Fearon、Daniel Akinbosede、Stephen Hare、John Spencer

  DOI：10.1021/acs.orglett.2c02996

  日期：2022.11.4

  A library of thiazoles and selenothiazoles were synthesized via Ir-catalyzed ylide insertion chemistry. This process is a functional group, particularly heterocycle-substituent tolerant. This was applied to the synthesis of fanetizole, an anti-inflammatory drug, and a thiazole-containing drug fragment that binds to the peptidyl-tRNA hydrolase (Pth) in Neisseria gonorrheae bacteria.

  通过 Ir 催化叶立德插入化学合成了噻唑和硒代噻唑库。这个过程是一个官能团，特别是杂环取代基的耐受性。该技术被应用于合成抗炎药法奈替唑以及与淋病奈瑟菌细菌中的肽基-tRNA水解酶（Pth）结合的含噻唑药物片段。