6-(4-Methoxyphenyl)-2-sulfanyl-4-(trifluoromethyl)pyridine-3-carbonitrile | 401649-63-6

• 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-sulfanyl-4-(trifluoromethyl)pyridine-3-carbonitrile
• 英文别名: 6-(4-methoxyphenyl)-2-sulfanylidene-4-(trifluoromethyl)-1H-pyridine-3-carbonitrile
• CAS: 401649-63-6
• 化学式: C₁₄H₉F₃N₂OS
• 分子量: 310.299
• InChiKey: WBGOVCCHVXTCRW-UHFFFAOYSA-N

物化性质

• 熔点：
  215-217 °C(Solv: ethanol (64-17-5))
• 沸点：
  354.2±52.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  6-(4-Methoxyphenyl)-2-sulfanyl-4-(trifluoromethyl)pyridine-3-carbonitrile 在 三溴化硼 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 2-(4-(3-amino-2-((4-fluorophenyl)carbamoyl)-4-(trifluoromethyl)thieno[2,3-b]pyridin-6-yl)phenoxy)acetic acid
  参考文献：
  名称：

  通过 E3 连接酶辅助降解靶向 FOXM1 癌蛋白

  摘要：

  通过选择性蛋白质-DNA和蛋白质-蛋白质相互作用调节多个增殖相关基因的转录因子FOXM1现在被认为是一种有吸引力的肿瘤靶点。有几种小分子抑制剂可间接抑制 FOXM1 的表达或阻断其 DNA 结合域 (FOXM1-DBD)。然而，特异性或/和功效不足是两个潜在的缺点。在这里，我们使用抑制剂对 FOXM1-DBD 进行计算机模拟，以设计一种有效的 CRBN 募集分子，该分子可诱导 FOXM1 蛋白的显着降解，并对 TNBC 异种移植模型产生有希望的体内抗肿瘤活性。这项研究首次展示了使用文献中描述的蛋白质靶向嵌合体来降解难以捉摸的 FOXM1 的方法，

  DOI：

  10.1021/acs.jmedchem.1c01069
• 作为产物：
  描述：

  对甲氧基苯乙酮 在 三乙烯二胺 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 生成 6-(4-Methoxyphenyl)-2-sulfanyl-4-(trifluoromethyl)pyridine-3-carbonitrile
  参考文献：
  名称：

  Discovery and structure–activity relationships study of novel thieno[2,3-b]pyridine analogues as hepatitis C virus inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2014.01.075

文献信息

• The synthesis of substituted 5-aminopyrido[3′,2′:4,5]thieno[3,2-c]isoquinolines and their sulfinyl and sulfonyl derivatives
  作者：V. E. Kalugin、A. M. Shestopalov

  DOI：10.1007/s11172-018-2155-y

  日期：2018.5

  Abstract5-Aminopyrido[3′,2′:4,5]thieno[3,2-c]isoquinolines were synthesized via alkylation of 3-cyanopyridine-2(1H)-thiones with 2-(chloromethyl)benzonitrile followed by treatment of the products with potassium tert-butoxide. The oxidation of the alkylated products to corresponding sulfoxides or sulfones followed by treatment with potassium tert-butoxide provided the corresponding 11-oxides or 11,11-dioxides

  摘要 5-氨基吡啶并[3',2':4,5]噻吩并[3,2-c]异喹啉是通过3-氰基吡啶-2(1H)-硫酮与2-(氯甲基)苄腈的烷基化反应合成的。与叔丁醇钾的产物。烷基化产物氧化成相应的亚砜或砜，然后用叔丁醇钾处理，得到相应的11-氧化物或11，11-二氧化物。
• 靶向泛素化降解FoxM1的化合物或其可药用的盐、制备方法及用途
  申请人：中国药科大学

  公开号：CN113234090B

  公开（公告）日：2022-07-29

  本发明公开了靶向降解FoxM1的化合物或其可药用的盐、制备方法及用途。结构如通式(I)所示。实验结果显示，与FoxM1抑制剂FDI‑6相比，本发明的化合物可有效降解转录因子FoxM1，尤其是化合物F‑8，在细胞和动物水平均表现出较好的抗乳腺癌活性。
• [DE] SUBSTITUIERTE PYRIDO [3',2':4,5]THIENO[3,2-D]PYRIMIDIN-2,4(1 H,3H)-DIONES UND -4(3H)-ONE SOWIE PYRIDO [3',2' :4,5] FURO[3,2-D]PYRIMIDIN -2,4(1 H,3H)-DIONE UND -4(3H)-ONE ZUR VERWENDUNG ALS INHIBITOREN DER TNF-ALLPHA FREISETZUNG<br/>[EN] SUBSTITUTED PYRIDO[3',2':4,5]THIENO[3,2-D]PYRIMIDINE-2,4(1 H,3H)-DIONES AND -4(3H)-ONES, PYRIDO[3',2':4,5]FURO[3,2-D]PYRIMIDINE-2,4(1 H,3H)-DIONES AND -4(3H)-ONES, AND USE THEREOF AS INHIBITORS OF TNF-ALPHA RELEASE<br/>[FR] PYRIDO[3',2':4,5]THIENO[3,2-D]PYRIMIDINE-2,4(1 H,3H)-DIONES ET PYRIDO[3',2':4,5]THIENO[3,2-D]PYRIMIDIN-4(3H)-ONES SUBSTITUEES, THIENO[2,3-D:4,5-D']DIPYRIMIDINE-2,4(1 H,3H)-DIONES ET THIENO[2,3-D:4,5-D']DIPYRIMIDIN-4(3H)-ONES SUBSTITUEES, PYRIDO[3',2'
  申请人：CURACYTE DISCOVERY GMBH

  公开号：WO2006010568A3

  公开（公告）日：2006-09-14
• [DE] SUBSTITUIERTE PYRIDO<br/>[EN] SUBSTITUTED PYRIDO[3',2':4,5]THIENO[3,2-D]PYRIMIDINE-2,4(1 H,3H)-DIONES AND -4(3H)-ONES, SUBSTITUTED THIENO[2,3-D:4,5-D']DIPYRIMIDINE-2,4(1 H,3H)-DIONES AND -4(3H)-ONES, SUBSTITUTED PYRIDO[3',2':4,5]FURO[3,2-D]PYRIMIDINE-2,4(1 H,3H)-DIONES AND -4(3H)<br/>[FR] PYRIDO[3',2':4,5]THIENO[3,2-D]PYRIMIDINE-2,4(1 H,3H)-DIONES ET PYRIDO[3',2':4,5]THIENO[3,2-D]PYRIMIDIN-4(3H)-ONES SUBSTITUEES, THIENO[2,3-D:4,5-D']DIPYRIMIDINE-2,4(1 H,3H)-DIONES ET THIENO[2,3-D:4,5-D']DIPYRIMIDIN-4(3H)-ONES SUBSTITUEES, PYRIDO[3',2'
  申请人：CURACYTE DISCOVERY GMBH

  公开号：WO2006010568A2

  公开（公告）日：2006-02-02

  Die Erfindung betrifft neue Pyrido[3',2':4,5]thieno[3,2-d]pyrimidin-2,4(1 H,3H)-dione und -4(3H)-one (X=C-H, Y=S), Thieno[2,3-d:4,5-d']dipyrimidin-2,4(1 H,3H)-dione und -4(3H)-one (X=N, Y=S) sowie Pyrido[3',2':4,5]furo[3,2-d]pyrimidin-2,4(1 H,3H)-dione und -4(3H)-one (X=C-H, Y=0) und Furo[2,3-d:4,5-d']dipyrimidin-2,4(1 H,3H)-dione und -4(3H)-one (X=N, Y=O) der allgemeinen Formeln 1 a und 1 b, Verfahren zu deren Herstellung, pharmazeutische Zubereitungen, die diese Verbindungen und/oder deren Tautomere und daraus herstelibare physiologisch verträgliche Salze und/oder deren Solvate enthalten, sowie die pharmazeutische Verwendung dieser Verbindungen, deren Tautomere, Salze oder Solvate, als Inhibitoren der TNFα-Freisetzung.
• 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.