3-amino-6-(thiazol-2-yl)thieno[2,3-b]pyridine-2-carboxamide | 1257317-82-0

• 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-(thiazol-2-yl)thieno[2,3-b]pyridine-2-carboxamide
• 英文别名: 3-Amino-6-(1,3-thiazol-2-yl)thieno[2,3-b]pyridine-2-carboxamide
• CAS: 1257317-82-0
• 化学式: C₁₁H₈N₄OS₂
• 分子量: 276.343
• InChiKey: PQQANVPSMGCLIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  151
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  6-(thiazol-2-yl)-3-cyanopyridine-2-(1H)-thione 、 氯乙酰胺 在 potassium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以70%的产率得到3-amino-6-(thiazol-2-yl)thieno[2,3-b]pyridine-2-carboxamide
  参考文献：
  名称：

  Novel thienopyridine derivatives as specific anti-hepatocellular carcinoma (HCC) agents: Synthesis, preliminary structure–activity relationships, and in vitro biological evaluation

  摘要：

  Novel thienopyridine derivatives 1b-1r were synthesized, based on a hit compound 1a that was found in a previous cell-based screening of anticancer drugs. Compounds 1a-1r have the following features: (1) their anticancer activity in vitro was first reported by our group. (2) The most potent analog 1g possesses hepatocellular carcinoma (HCC)-specific anticancer activity. It can specifically inhibit the proliferation of the human hepatoma HepG2 cells with an IC(50) value of 0.016 mu M (compared with doxorubicin as a positive control, whose IC(50) was 0.37 mu M). It is inactive toward a panel of five different types of human cancer cell lines. (3) Compound 1g remarkably induces G(0)/G(1) arrest and apoptosis in HepG2 cells in vitro at low micromolar concentrations. These results, especially the HCC-specific anticancer activity of 1g, suggest their potential in targeted chemotherapy for HCC. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.088

文献信息

• Synthesis, preliminary structure–activity relationships, and in vitro biological evaluation of 6-aryl-3-amino-thieno[2,3-b]pyridine derivatives as potential anti-inflammatory agents
  作者：Huan Liu、Yi Li、Xiang-Ying Wang、Bo Wang、Hai-Yun He、Ji-Yan Liu、Ming-Li Xiang、Jun He、Xiao-Hua Wu、Li Yang

  DOI：10.1016/j.bmcl.2013.02.059

  日期：2013.4

  In our previous study, a series of 6-aryl-3-amino-thieno[2,3-b]pyridine derivatives exhibited potent anti-proliferative activities and an unique hepatocellular carcinoma (HCC)-specific anticancer activity was also observed. In further anti-inflammatory research, thienopyridine derivative 1a showed potent inhibition of nitric oxide (NO) production. So a series of thienopyridine analogues of 1a were synthesized and evaluated for anti-inflammatory activities. The structure-activity relationships (SARs) revealed that the most potent analogues 1f and 1o were identified as potent inhibitors of NO production with IC50 values of 3.30 and 3.24 mu M, respectively. These results suggest that these 6-aryl-3-amino-thieno[2,3-b]pyridine derivatives might potentially constitute a novel class of anti-inflammatory agents, which require further studies. (C) 2013 Elsevier Ltd. All rights reserved.
• Novel thienopyridine derivatives as specific anti-hepatocellular carcinoma (HCC) agents: Synthesis, preliminary structure–activity relationships, and in vitro biological evaluation
  作者：Xiu-Xiu Zeng、Ren-Lin Zheng、Tian Zhou、Hai-Yun He、Ji-Yan Liu、Yu Zheng、Ai-Ping Tong、Ming-Li Xiang、Xiang-Rong Song、Sheng-Yong Yang、Luo-Ting Yu、Yu-Quan Wei、Ying-Lan Zhao、Li Yang

  DOI：10.1016/j.bmcl.2010.08.088

  日期：2010.11

  Novel thienopyridine derivatives 1b-1r were synthesized, based on a hit compound 1a that was found in a previous cell-based screening of anticancer drugs. Compounds 1a-1r have the following features: (1) their anticancer activity in vitro was first reported by our group. (2) The most potent analog 1g possesses hepatocellular carcinoma (HCC)-specific anticancer activity. It can specifically inhibit the proliferation of the human hepatoma HepG2 cells with an IC(50) value of 0.016 mu M (compared with doxorubicin as a positive control, whose IC(50) was 0.37 mu M). It is inactive toward a panel of five different types of human cancer cell lines. (3) Compound 1g remarkably induces G(0)/G(1) arrest and apoptosis in HepG2 cells in vitro at low micromolar concentrations. These results, especially the HCC-specific anticancer activity of 1g, suggest their potential in targeted chemotherapy for HCC. (C) 2010 Elsevier Ltd. All rights reserved.