3-amino-6-(2-thienyl)-4-trifluoromethylthieno[2,3-b]pyridine-2-carboxylic acid | 625375-64-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: 3-amino-6-(2-thienyl)-4-trifluoromethylthieno[2,3-b]pyridine-2-carboxylic acid
• 英文别名: 3-Amino-6-thiophen-2-yl-4-(trifluoromethyl)thieno[2,3-b]pyridine-2-carboxylic acid
• CAS: 625375-64-6
• 化学式: C₁₃H₇F₃N₂O₂S₂
• 分子量: 344.338
• InChiKey: OTQTXJFOCPWUAB-UHFFFAOYSA-N

物化性质

• 熔点：
  209-210 °C(Solv: ethanol (64-17-5); chloroform (67-66-3))
• 沸点：
  557.5±50.0 °C(Predicted)
• 密度：
  1.644±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-amino-6-(2-thienyl)-4-trifluoromethylthieno[2,3-b]pyridine-2-carboxylic acid 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 3-amino-7-(2-thienyl)-9-trifluoromethylpyrido[3',2':4,5]thieno[3,2-d]pyrimidine-4(3H)-one
  参考文献：
  名称：

  Abdel-Rahman, Abdu E.; Bakhite, Etify A.; Al-Taifi, Elham A., Journal of Chemical Research, 2005, # 7, p. 461 - 468

  摘要：

  DOI：
• 作为产物：
  描述：

  2-噻吩甲酰三氟丙酮 在 三乙烯二胺 、 potassium hydroxide 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-amino-6-(2-thienyl)-4-trifluoromethylthieno[2,3-b]pyridine-2-carboxylic acid
  参考文献：
  名称：

  Discovery and structure–activity relationships study of novel thieno[2,3-b]pyridine analogues as hepatitis C virus inhibitors

  摘要：

  Current treatment for hepatitis C is barely satisfactory, there is an urgent need to develop novel agents for combating hepatitis C virus infection. This study discovered a new class of thieno[ 2,3-b] pyridine derivatives as HCV inhibitors. First, a hit compound characterized by a thienopyridine core was identified in a cell-based screening of our privileged small molecule library. And then, structure activity relationship study of the hit compound led to the discovery of several potent compounds without obvious cytotoxicity in vitro (12c, EC50 = 3.3 mu M, SI > 30.3, 12b, EC50 = 3.5 mu M, SI > 28.6, 10l, EC50 = 3.9 mu M, SI > 25.6, 12o, EC50 = 4.5 mu M, SI > 22.2, respectively). Although the mechanism of them had not been clearly elucidated, our preliminary optimization of this class of compounds had provided us a start point to develop new anti-HCV agents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.075

文献信息

• Thienopyridine Derivatives for the Treatment and Prevention of Dengue Virus Infections
  申请人：Siga Technologies, Inc.

  公开号：US20130129677A1

  公开（公告）日：2013-05-23

  Methods and pharmaceutical compositions for treating viral infections, by administering certain thienopyridine derivative compounds in therapeutically effective amounts are disclosed. Methods of using the compounds and pharmaceutical compositions thereof are also disclosed. In particular, the treatment of viral infections such as caused by flavivirus is disclosed, i.e., including but not limited to, Dengue virus, West Nile virus, yellow fever virus, Japanese encephalitis virus, and tick-borne encephalitis virus.

  本发明揭示了使用某些噻唑吡啶衍生物化合物以治疗病毒感染的方法和制药组合物，通过以治疗有效剂量给药。同时还揭示了使用这些化合物和制药组合物的方法。具体地，揭示了治疗由黄热病毒、日本脑炎病毒、西尼罗河病毒、登革热病毒和蜱媒脑炎病毒等引起的病毒感染的方法。
• THIENOPYRIDINE DERIVATIVES FOR THE TREATMENT AND PREVENTION OF DENGUE VIRUS INFECTIONS
  申请人：Siga Technologies, Inc.

  公开号：US20160152635A1

  公开（公告）日：2016-06-02

  Methods and pharmaceutical compositions for treating viral infections, by administering certain thienopyridine derivative compounds in therapeutically effective amounts are disclosed. Methods of using the compounds and pharmaceutical compositions thereof are also disclosed. In particular, the treatment and prophylaxis of viral infections such as caused by flavivirus is disclosed, i.e., including but not limited to, Dengue virus, West Nile virus, yellow fever virus, Japanese encephalitis virus, and tick-borne encephalitis virus.

  本发明公开了通过以治疗有效剂量给予某些噻唑吡啶衍生物化合物来治疗病毒感染的方法和制药组合物。本发明还公开了使用这些化合物和其制药组合物的方法。具体而言，本发明公开了治疗和预防由黄热病毒、日本脑炎病毒、蜱传脑炎病毒等引起的病毒感染的方法，但不限于此。
• US9301949B2
  申请人：——

  公开号：US9301949B2

  公开（公告）日：2016-04-05
• Discovery and structure–activity relationships study of novel thieno[2,3-b]pyridine analogues as hepatitis C virus inhibitors
  作者：Ning-Yu Wang、Wei-Qiong Zuo、Ying Xu、Chao Gao、Xiu-Xiu Zeng、Li-Dan Zhang、Xin-Yu You、Cui-Ting Peng、Yang Shen、Sheng-Yong Yang、Yu-Quan Wei、Luo-Ting Yu

  DOI：10.1016/j.bmcl.2014.01.075

  日期：2014.3

  Current treatment for hepatitis C is barely satisfactory, there is an urgent need to develop novel agents for combating hepatitis C virus infection. This study discovered a new class of thieno[ 2,3-b] pyridine derivatives as HCV inhibitors. First, a hit compound characterized by a thienopyridine core was identified in a cell-based screening of our privileged small molecule library. And then, structure activity relationship study of the hit compound led to the discovery of several potent compounds without obvious cytotoxicity in vitro (12c, EC50 = 3.3 mu M, SI > 30.3, 12b, EC50 = 3.5 mu M, SI > 28.6, 10l, EC50 = 3.9 mu M, SI > 25.6, 12o, EC50 = 4.5 mu M, SI > 22.2, respectively). Although the mechanism of them had not been clearly elucidated, our preliminary optimization of this class of compounds had provided us a start point to develop new anti-HCV agents. (C) 2014 Elsevier Ltd. All rights reserved.
• Abdel-Rahman, Abdu E.; Bakhite, Etify A.; Al-Taifi, Elham A., Journal of Chemical Research, 2005, # 7, p. 461 - 468
  作者：Abdel-Rahman, Abdu E.、Bakhite, Etify A.、Al-Taifi, Elham A.

  DOI：——

  日期：——