6-(biphenyl-4-yl)-3-cyanopyridine-2-(1H)-thione | 1257317-86-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(biphenyl-4-yl)-3-cyanopyridine-2-(1H)-thione
• 英文别名: 6-(4-phenylphenyl)-2-sulfanylidene-1H-pyridine-3-carbonitrile
• CAS: 1257317-86-4
• 化学式: C₁₈H₁₂N₂S
• 分子量: 288.373
• InChiKey: MWQCBDGQQKPYBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 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：
  67.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(biphenyl-4-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80%的产率得到3-amino-6-(biphenyl-4-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
• 作为产物：
  描述：

  联苯单乙酮 在 三乙烯二胺 作用下， 以 乙醇 为溶剂， 生成 6-(biphenyl-4-yl)-3-cyanopyridine-2-(1H)-thione
  参考文献：
  名称：

  Facile Synthesis of 6-Aryl-3-cyanopyridine-2-(1H)-thiones from Aryl Ketones

  摘要：

  An improved synthesis of 6-aryl-3-cyanopyridine-2-(1H)-thiones utilizing enaminones as starting materials catalyzed by 1,4-diazabicyclo[2.2.2] octane (DABCO) was described. Moreover, a convenient one-pot conversion of aryl ketones to 6-aryl-3-cyanopyridine- 2-(1H)-thiones was also developed in moderate to good yields (up to 80%).

  DOI：

  10.1080/00397911.2010.541964

文献信息

• Facile Synthesis of 6-Aryl-3-cyanopyridine-2-(1<i>H</i>)-thiones from Aryl Ketones
  作者：Ren-Lin Zheng、Xiu-Xiu Zeng、Hai-Yun He、Jun He、Sheng-Yong Yang、Luo-Ting Yu、Li Yang

  DOI：10.1080/00397911.2010.541964

  日期：2012.5.15

  An improved synthesis of 6-aryl-3-cyanopyridine-2-(1H)-thiones utilizing enaminones as starting materials catalyzed by 1,4-diazabicyclo[2.2.2] octane (DABCO) was described. Moreover, a convenient one-pot conversion of aryl ketones to 6-aryl-3-cyanopyridine- 2-(1H)-thiones was also developed in moderate to good yields (up to 80%).
• 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.