3-amino-6-(4-methoxyphenyl)thieno[2,3-b]pyridine-2-carboxylic acid | 383407-52-1

• 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-(4-methoxyphenyl)thieno[2,3-b]pyridine-2-carboxylic acid
• CAS: 383407-52-1
• 化学式: C₁₅H₁₂N₂O₃S
• 分子量: 300.338
• InChiKey: ILZCYNVTSDEOKX-UHFFFAOYSA-N

物化性质

• 熔点：
  238-240 °C
• 沸点：
  577.2±50.0 °C(Predicted)
• 密度：
  1.427±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ethyl 3-amino-6-(4-methoxyphenyl)thieno[2,3-b]pyridine-2-carboxylate 生成 3-amino-6-(4-methoxyphenyl)thieno[2,3-b]pyridine-2-carboxylic acid
  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

• 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.