ethyl 3-amino-6-phenyl-4-trifluoromethylthiophene[2,3-b]pyridine-2-ethyl ester | 299165-10-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: ethyl 3-amino-6-phenyl-4-trifluoromethylthiophene[2,3-b]pyridine-2-ethyl ester
• 英文别名: ethyl 3-amino-6-phenyl-4-(trifluoromethyl)thieno[2,3-b]pyridine-2-carboxylate
• CAS: 299165-10-9
• 化学式: C₁₇H₁₃F₃N₂O₂S
• 分子量: 366.364
• InChiKey: FIIQBNRDZWSSDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 3-amino-6-phenyl-4-trifluoromethylthiophene[2,3-b]pyridine-2-ethyl ester 在 亚硝酸特丁酯 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 [3-amino-6-phenyl-4-(trifluoromethyl)thieno[2,3-b]pyridin-2-yl]-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]methanone
  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
• 作为产物：
  描述：

  苯甲酰三氟丙酮 在 三乙烯二胺 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl 3-amino-6-phenyl-4-trifluoromethylthiophene[2,3-b]pyridine-2-ethyl ester
  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

• A new series of HCV inhibitors based on a 2-(thieno[2,3b]pyridin-2-yl)-1,3,4-oxadiazole scaffold
  作者：Wei-Qiong Zuo、Ning-Yu Wang、Yong-xia Zhu、Li Liu、Kun-Jie Xiao、Li-Dan Zhang、Chao Gao、Zhi-Hao Liu、Xin-Yu You、Yao-Jie Shi、Cui-Ting Peng、Kai Ran、Hong Tang、Luo-Ting Yu

  DOI：10.1039/c6ra01179a

  日期：——

  A new series of HCV inhibitors based on a 2-(thieno[2,3-b]pyridin-2-yl)-1,3,4-oxadiazole scaffold was developed.

  基于2-(噻吩[2,3-b]吡啶-2-基)-1,3,4-噁二唑骨架开发了一系列新的HCV抑制剂。
• 2-噁二唑-3-氨基噻吩并[2,3-b]吡啶衍生物 及其制备方法和用途
  申请人：四川大学

  公开号：CN106928250B

  公开（公告）日：2019-09-27

  本发明属于化学制药领域，具体涉及2‑噁二唑‑3‑氨基噻吩并[2,3‑b]吡啶衍生物及其制备方法和用途。本发明提供了一种2‑噁二唑‑3‑氨基噻吩并[2,3‑b]吡啶衍生物，其结构如式Ⅰ所示。本发明还提供了上述2‑噁二唑‑3‑氨基噻吩并[2,3‑b]吡啶衍生物到制备方法和用途。本发明提供的2‑噁二唑‑3‑氨基噻吩并[2,3‑b]吡啶衍生物化合物有良好的HCV抑制效果，同时表现出了较低的细胞毒性。为抗HCV抑制剂的开发提供新思路。
• Synthesis of Novel Trifluoromethyl Group Containing Pyrido Furo/Thieno Pyrimidinone Derivatives and Their Anticancer Activity
  作者：Hanumandlu Racha、Balakishan Vadla、Kavitha Peddolla、Sailu Betala

  DOI：10.1002/jhet.3566

  日期：2019.6

  Compound 4 on reaction with trifluoroacetic acid and obtained novel trifluoromethyl group containing pyridofuro/thieno pyrimidinone derivatives 5a–p. All the synthesized compounds 5a–p were tested for anticancer activity on four cancer cell lines such as HeLa cervical cancer (CCL‐2), COLO 205 colon cancer (CCL‐222), HepG2 liver cancer (HB‐8065), MCF7 breast cancer (HTB‐22), and one normal cell line

  从2-氧代/硫代氧-6-苯基/噻吩-2-基-4-（三氟甲基）-1,2-二氢吡啶-3-碳腈开始制备了一系列新颖的含三氟甲基/吡啶酮/噻吩并嘧啶酮衍生物5a-p 1化合物与溴乙酸乙酯和其他不同的脂肪族伯胺在回流条件下反应，得到酰胺标记的呋喃/噻吩并吡啶衍生物4。化合物4与三氟乙酸反应，获得了新颖的含三氟甲基的吡啶并/噻吩并嘧啶酮衍生物5a-p。所有合成的化合物5a–p测试了四种癌细胞系的抗癌活性，例如HeLa宫颈癌（CCL-2），COLO 205结肠癌（CCL-222），HepG2肝癌（HB-8065），MCF7乳腺癌（HTB-22）和1个正常细胞系（HEK 293）；发现化合物5m，5n和5p在微摩尔浓度下具有更好的抗癌活性，并且对正常细胞系无毒。
• Synthesis of Novel Alkyl Amide Functionalized Trifluoromethyl Substituted Furo/thieno Pyridine Derivatives: Their Anticancer Activity and CoMFA and CoMSIA Studies
  作者：Srinu Bhoomandla、Shravan Kumar Gunda、Srawanthi Kotoori、Phani Raja Kanuparthy

  DOI：10.1002/jhet.3578

  日期：2019.7

  6a–h were screened for anticancer activity against four cancer cell lines such as HeLa—cervical cancer (CCL‐2), COLO205—colon cancer (CCL‐222), HepG2—liver cancer (HB‐8065), and MCF7—breast cancer (HTB‐22). Compounds 4g and 4h are found to have promising anticancer activity at micromolar concentration. CoMFA and CoMSIA methods were applied to derive 3D‐QSAR models for alkyl amide tagged furo/thieno

  从2-氧代/硫代氧-6-苯基/噻吩-2-基-4-（三氟甲基）开始制备了一系列新颖的烷基酰胺官能化的三氟甲基取代的呋喃/硫代吡啶衍生物4a-h，5a-d和6a-h）1,2-二氢吡啶-3-腈1与溴乙酸乙酯反应，然后在不同的条件下与不同的脂肪族伯胺，环状仲胺或l-氨基酸反应。所有合成的化合物4a–h，5a–d和6a–h筛选了针对四种癌细胞系的抗癌活性，例如HeLa-宫颈癌（CCL-2），COLO205-结肠癌（CCL-222），HepG2-肝癌（HB-8065）和MCF7-乳腺癌（HTB- 22）。发现化合物4g和4h在微摩尔浓度下具有有希望的抗癌活性。应用CoMFA和CoMSIA方法获得了3D-QSAR模型，用于烷基酰胺标记的呋喃/噻吩并吡啶衍生物作为潜在的抗癌抑制剂。3D-QSAR模型为将来更合理地设计更具活性和选择性的HeLa，COLO205，HepG2和MCF-7细胞系抑制剂提供了坚实的基础。
• 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.