1,2-Dihydro-6-(2-naphthalenyl)-2-thioxo-3-pyridinecarbonitrile | 1187616-18-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,2-Dihydro-6-(2-naphthalenyl)-2-thioxo-3-pyridinecarbonitrile
• 英文别名: 6-naphthalen-2-yl-2-sulfanylidene-1H-pyridine-3-carbonitrile
• CAS: 1187616-18-7
• 化学式: C₁₆H₁₀N₂S
• 分子量: 262.335
• InChiKey: WWOLHAZSAGMQBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  1
• 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：

  1,2-Dihydro-6-(2-naphthalenyl)-2-thioxo-3-pyridinecarbonitrile 、 氯乙酰胺 在 potassium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以63%的产率得到3-amino-6-(naphthalen-2-yl)thieno[2,3-b]pyridine-2-carboxamide
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2013.02.059
• 作为产物：
  描述：

  2-萘乙酮 在 三乙烯二胺 作用下， 以 乙醇 为溶剂， 生成 1,2-Dihydro-6-(2-naphthalenyl)-2-thioxo-3-pyridinecarbonitrile
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2013.02.059

文献信息

• Synthesis and anti-tumor activities of some new pyridines and pyrazolo[1,5-a]pyrimidines
  作者：Osama M. Ahmed、Mahmoud A. Mohamed、Rasha R. Ahmed、Sayed A. Ahmed

  DOI：10.1016/j.ejmech.2009.03.042

  日期：2009.9

  cyanoacetamide, cyanothioacetamide and 3-aminopyrazols with sodium salt of 3-hydroxy-1-(2-naphthyl)prop-2-en-1-one gives pyridin-2-one, pyridin-2(1H)-thione, and pyrazolo[1,5-a]pyrimidine derivatives. These derivatives showed potent anti-tumor cytotoxic activity in vitro using different human cancer cell lines.

  氰基乙酰胺，氰基硫代乙酰胺和3-氨基吡唑与3-羟基-1-（2-萘基）丙-2-烯-1-酮的钠盐进行环缩合可得到吡啶-2-酮，吡啶-2（1 H）-硫酮，和吡唑并[1，5- a ]嘧啶衍生物。这些衍生物在体外使用不同的人类癌细胞系显示出有效的抗肿瘤细胞毒活性。
• 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.