6-(4-methoxyphenyl)-2-thioxo-1,2-dihydropyridine-3-carbonitrile | 118947-85-6

• 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: 6-(4-methoxyphenyl)-2-thioxo-1,2-dihydropyridine-3-carbonitrile
• 英文别名: 6-(4-methoxyphenyl)-3-cyanopyridine-2-(1H)-thione；2-Mercapto-6-(4-methoxyphenyl)nicotinonitrile；6-(4-methoxyphenyl)-2-sulfanylidene-1H-pyridine-3-carbonitrile
• CAS: 118947-85-6
• 化学式: C₁₃H₁₀N₂OS
• mdl: MFCD19026446
• 分子量: 242.301
• InChiKey: LPVDGFPBIJUBEI-UHFFFAOYSA-N

物化性质

• 沸点：
  389.0±52.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

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-(4-methoxyphenyl)-2-thioxo-1,2-dihydropyridine-3-carbonitrile 在 氢氧化钾 、 溴 作用下， 以 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  腈的环化反应。29. 6-芳基-3-氰基-2（1H）-吡啶硫酮及其相应硒酮的区域选择性合成及其特征

  摘要：

  DOI：

  10.1007/bf00475603
• 作为产物：
  描述：

  对甲氧基苯乙酮 在 乙酸哌啶酯 、 sodium methylate 作用下， 以 乙醚 、 水 为溶剂， 反应 0.25h， 生成 6-(4-methoxyphenyl)-2-thioxo-1,2-dihydropyridine-3-carbonitrile
  参考文献：
  名称：

  通过TD-DFT计算和分子动力学模拟研究6-苯基-2-硫代-1,2-二氢吡啶-3-甲腈衍生物的溶剂化作用

  摘要：

  摘要 对6-苯基-2-硫代-1,2-二氢吡啶-3-甲腈（2-mercapto-6-phenylpyridine-3-carbonitrile）及其衍生物的电子结构进行了理论和实验研究。选择这些化合物的动机是它们的生物学重要性和相关性。FT-IR 分光光度计、1HNMR 光谱和 XRD 谱证实了这项工作中所有研究衍生物的相应结构。密度泛函理论 (DFT) 已被用于研究具有不同强度的取代基对所有研究化合物的几何结构、自然键轨道 (NBO) 特性、静电势 (ESP) 和全局特性的影响，例如（化学硬度 (η), 整体柔软度 (S), 和电负性 (χ) 通过分析气相分子中的电荷分布和电荷转移程度。非线性光学特性 (NLO)，例如（静态偶极矩 (μ)、极化率 (α)、各向异性极化率 (Δα)、一阶超极化率 (β) 和平均二阶超极化率 (γ)）也通过 DFT 计算在气相和溶剂（苯和乙醇）相中。还研究了不同取代和溶剂极性对

  DOI：

  10.1016/j.molstruc.2019.127056

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%).
• 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.
• 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.
• 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.
• 3-Amino-thieno[2,3-b]pyridines as microtubule-destabilising agents: Molecular modelling and biological evaluation in the sea urchin embryo and human cancer cells
  作者：Chatchakorn Eurtivong、Victor Semenov、Marina Semenova、Leonid Konyushkin、Olga Atamanenko、Jóhannes Reynisson、Alex Kiselyov

  DOI：10.1016/j.bmc.2016.11.041

  日期：2017.1

  A series of 3-amino-thieno[2,3-b]pyridines was prepared and tested in a phenotypic sea urchin embryo assay to identify potent and specific molecules that affect tubulin dynamics. The most active compounds featured a tricyclic core ring system with a fused cycloheptyl or cyclohexyl substituent and unsubstituted or alkyl-substituted phenyl moiety tethered via a carboxamide. Low nano-molar potency was observed in the sea urchin embryos for the most active compounds (1-5) suggestive of a microtubule-destabilising effect. The molecular modelling studies indicated that the tubulin colchicine site is inhibited, which often leads to microtubule-destabilisation in line with the sea urchin embryo results. Finally, the identified hits displayed a robust growth inhibition (GI(50) of 50-250 nM) of multidrug-resistant melanoma MDA-MB-435 and breast MDA-MB-468 human cancer cell lines. This work demonstrates that for the thieno[2,3-b]pyridines the most effective mechanism of action is microtubule-destabilisation initiated by binding to the colchicine pocket. (C) 2016 Elsevier Ltd. All rights reserved.