6-(2-甲氧基苯基)-3-氰基吡啶-2-(1H)-硫酮 | 1035830-63-7

• 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
• 中文名称: 6-(2-甲氧基苯基)-3-氰基吡啶-2-(1H)-硫酮
• 英文名称: 6-(2-methoxyphenyl)-3-cyanopyridine-2-(1H)-thione
• 英文别名: 6-(2-methoxyphenyl)-2-sulfanylidene-1H-pyridine-3-carbonitrile
• CAS: 1035830-63-7
• 化学式: C₁₃H₁₀N₂OS
• mdl: MFCD13813409
• 分子量: 242.301
• InChiKey: TVMJLSDRIOXYNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(2-甲氧基苯基)-3-氰基吡啶-2-(1H)-硫酮 、 氯乙酰胺 在 potassium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以30%的产率得到3-amino-6-(2-methoxyphenyl)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：

  2'-甲氧基苯乙酮 在 三乙烯二胺 作用下， 以 乙醇 为溶剂， 生成 6-(2-甲氧基苯基)-3-氰基吡啶-2-(1H)-硫酮
  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

• 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.
• 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.