N-(4-aminophenyl)-4-(4-chlorophenyl)-1,3-thiazole-2-amine | 309732-78-3

• 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-aminophenyl)-4-(4-chlorophenyl)-1,3-thiazole-2-amine
• 英文别名: N1-(4-(4-chlorophenyl)thiazol-2-yl)benzene-1,4-diamine；4-N-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]benzene-1,4-diamine
• CAS: 309732-78-3
• 化学式: C₁₅H₁₂ClN₃S
• mdl: MFCD02045245
• 分子量: 301.799
• InChiKey: BUROQFHRHNMPDU-UHFFFAOYSA-N

物化性质

• 沸点：
  511.1±60.0 °C(predicted)
• 密度：
  1.386±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 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：
  79.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (4-amino-phenyl)-thiourea 、 2'-溴-4-氯苯乙酮 以 乙醇 为溶剂， 生成 N-(4-aminophenyl)-4-(4-chlorophenyl)-1,3-thiazole-2-amine
  参考文献：
  名称：

  2-Anilino-4-aryl-1,3-thiazole inhibitors of valosin-containing protein (VCP or p97)

  摘要：

  Valosin-containing protein (VCP; also known as p97) is a member of the AAA ATPase family with a central role in the ubiquitin-degradation of misfolded proteins. VCP also exhibits antiapoptotic function and metastasis via activation of nuclear factor kappa-B signaling pathway. We have discovered that 2-anilino-4-aryl-1,3-thiazoles are potent drug-like inhibitors of this enzyme. The identified compounds show low nanomolar VCP potency, demonstrate SAR trends, and show activity in a mechanism based cellular assay. This series of compounds represents the first steps towards a novel, small molecule VCP inhibitor as a cancer therapeutic. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.058

文献信息

• 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。
• Thiazole compounds and methods of use
  申请人：Zhang Suoming

  公开号：US20070004711A1

  公开（公告）日：2007-01-04

  The present invention provides compounds, salts and hydrates of Formula I, wherein the variables Ar 1 , R 2 , R 3 , R 4 , r, q, and t are defined herein. Certain compounds of Formula I described herein possess potent antiviral activity. The invention also provides compounds of Formula I that are potent and/or selective inhibitors of Hepatitis C virus replication. Certain compounds described herein inhibit assembly of the HCV replication complex. The invention also provides pharmaceutical compositions containing one or more compounds of Formula I, or a salt, solvate, or acylated prodrug of such compounds, and one or more pharmaceutically acceptable carriers, excipients, or diluents. The invention further comprises methods of treating patients suffering from certain infectious diseases by administering to such patients an amount of a compound of Formula I effective to reduce signs or symptoms of the disease. These infectious diseases include viral infections, particularly HCV infections. The invention is particularly includes methods of treating human patients suffering from an infectious disease, but also encompasses methods of treating other animals, including livestock and domesticated companion animals, suffering from an infectious disease. Methods of treatment include administering a compound of Formula I as a single active agent or administering a compound of Formula I in combination with on or more other therapeutic agent.
• THIAZOLE COMPOUNDS AND METHODS OF USE
  申请人：Zhang Suoming

  公开号：US20120108576A1

  公开（公告）日：2012-05-03

  The present invention provides compounds, salts and hydrates of Formula I, wherein the variables Ar 1 , R 2 , R 3 , R 4 , r, q, and t are defined herein. Certain compounds of Formula I described herein possess potent antiviral activity. The invention also provides compounds of Formula I that are potent and/or selective inhibitors of Hepatitis C virus replication. Certain compounds described herein inhibit assembly of the HCV replication complex. The invention also provides pharmaceutical compositions containing one or more compounds of Formula I, or a salt, solvate, or acylated prodrug of such compounds, and one or more pharmaceutically acceptable carriers, excipients, or diluents. The invention further comprises methods of treating patients suffering from certain infectious diseases by administering to such patients an amount of a compound of Formula I effective to reduce signs or symptoms of the disease. These infectious diseases include viral infections, particularly HCV infections. The invention is particularly includes methods of treating human patients suffering from an infectious disease, but also encompasses methods of treating other animals, including livestock and domesticated companion animals, suffering from an infectious disease. Methods of treatment include administering a compound of Formula I as a single active agent or administering a compound of Formula I in combination with on or more other therapeutic agent.
• US8088806B2
  申请人：——

  公开号：US8088806B2

  公开（公告）日：2012-01-03
• 2-Anilino-4-aryl-1,3-thiazole inhibitors of valosin-containing protein (VCP or p97)
  作者：Matthew G. Bursavich、Daniel P. Parker、J. Adam Willardsen、Zhong-Hua Gao、Thaylon Davis、Kirill Ostanin、Rosann Robinson、Ashley Peterson、Daniel M. Cimbora、Ju-Fen Zhu、Burt Richards

  DOI：10.1016/j.bmcl.2010.01.058

  日期：2010.3

  Valosin-containing protein (VCP; also known as p97) is a member of the AAA ATPase family with a central role in the ubiquitin-degradation of misfolded proteins. VCP also exhibits antiapoptotic function and metastasis via activation of nuclear factor kappa-B signaling pathway. We have discovered that 2-anilino-4-aryl-1,3-thiazoles are potent drug-like inhibitors of this enzyme. The identified compounds show low nanomolar VCP potency, demonstrate SAR trends, and show activity in a mechanism based cellular assay. This series of compounds represents the first steps towards a novel, small molecule VCP inhibitor as a cancer therapeutic. (C) 2010 Elsevier Ltd. All rights reserved.