(3-amino-6-phenyl-4-(trifluoromethyl)thieno[2,3-b]pyridin-2-yl)(4-methylpiperazin-1-yl)methanone | 827008-47-9

• 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: (3-amino-6-phenyl-4-(trifluoromethyl)thieno[2,3-b]pyridin-2-yl)(4-methylpiperazin-1-yl)methanone
• 英文别名: [3-Amino-6-phenyl-4-(trifluoromethyl)thieno[2,3-b]pyridin-2-yl]-(4-methylpiperazin-1-yl)methanone
• CAS: 827008-47-9
• 化学式: C₂₀H₁₉F₃N₄OS
• 分子量: 420.458
• InChiKey: XHPAQNUACPCRIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  90.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  苯甲酰三氟丙酮 在 三乙烯二胺 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 potassium hydroxide 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3-amino-6-phenyl-4-(trifluoromethyl)thieno[2,3-b]pyridin-2-yl)(4-methylpiperazin-1-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

文献信息

• 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。