6-(thiophen-2-yl)-2-thioxo-1,2-dihydropyridine-3-carbonitrile | 190579-92-1

• 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-(thiophen-2-yl)-2-thioxo-1,2-dihydropyridine-3-carbonitrile
• 英文别名: 6-(2-Thienyl)-2-thioxo-1,2-dihydro-3-pyridinecarbonitrile；2-sulfanylidene-6-thiophen-2-yl-1H-pyridine-3-carbonitrile
• CAS: 190579-92-1
• 化学式: C₁₀H₆N₂S₂
• mdl: MFCD13813391
• 分子量: 218.303
• InChiKey: ZFOUAZBWQSIIIA-UHFFFAOYSA-N

物化性质

• 熔点：
  233-235 °C(Solv: acetic acid (64-19-7))
• 沸点：
  364.3±52.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(thiophen-2-yl)-2-thioxo-1,2-dihydropyridine-3-carbonitrile 在 哌啶 、 氢氧化钾 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 3-amino-6-(2-thienyl)thieno[2,3-b]pyridine-2-carbonitrile
  参考文献：
  名称：

  与腙酰卤的反应 45：合成一些新的三唑并[4,3-a]嘧啶、吡唑并[3,4-d]哒嗪、异恶唑并[3,4-d]哒嗪和噻吩并[2,3-b]吡啶

  摘要：

  摘要 三唑并[4,3-a]嘧啶类吡唑并[3,4-d]哒嗪和异恶唑并[3,4-d]哒嗪由腙酰卤化物合成。此外，3-氨基噻吩并[2,3-b]吡啶和嘧啶并[4',5':4,5]噻吩并[2,3-b]吡啶由犬硫代乙酰胺合成。新合成化合物的结构是在元素分析和光谱数据的基础上建立的。

  DOI：

  10.1080/00397910500330593
• 作为产物：
  描述：

  2-乙酰基噻吩 在 sodium ethanolate 作用下， 以 乙醇 、 xylene 为溶剂， 反应 11.0h， 生成 6-(thiophen-2-yl)-2-thioxo-1,2-dihydropyridine-3-carbonitrile
  参考文献：
  名称：

  SYNTHESIS OF NEW ARYL AND HETEROAROMATIC SUBSTITUTED PYRIDINES, PYRAZOLES, PYRIMIDINES AND PYRAZOLO[3,4-D]PYRIDAZINES

  摘要：

  DOI：

  10.1080/00304949709355198

文献信息

• Thienopyridine and benzofuran derivatives as potent anti-tumor agents possessing different structure–activity relationships
  作者：Ichiro Hayakawa、Rieko Shioya、Toshinori Agatsuma、Hidehiko Furukawa、Yuichi Sugano

  DOI：10.1016/j.bmcl.2004.04.079

  日期：2004.7

  (3 -Amino-6-thiophen-2-yl-thieno[2,3 -b]pyridin-2-yl)phenylmethanone (3) was discovered as a new type of cytotoxic agent selective against a tumorigenic cell line. The molecular structure of a previously reported compound, (4-hydroxy-3-methyl-6-phenylbenzofuran-2-yl)phenylmethanone (2), had remarkably similar bioisosteric substructures to that of compound 3. Although the relationship between the molecular structure and biological activity of each derivative synthesized from these two hit compounds (2 and 3) were studied, unexpectedly no correlation was observed. However, after further synthetic study from 3, one of the most potent derivative (10k) having a different SAR profile from 2, was discovered. (C) 2004 Elsevier Ltd. All rights reserved.

  (3-氨基-6-噻吩-2-基-苯并呋喃[2,3-b]吡啶-2-基)苯甲酸甲酯(3)被发现是一种新型的选择性细胞毒性剂，对肿瘤生成的细胞系具有选择性毒性。先前报道的化合物(4-羟基-3-甲基-6-苯基苯并呋喃-2-基)苯甲酸甲酯(2)的分子结构与化合物3具有显著相似的生物电子等排体亚结构。尽管对这两种化合物(2和3)衍生出的衍生物的分子结构与生物活性之间的关系进行了研究，但意外的是并未观察到明显的相关性。然而，在对3进行进一步的合成研究后，发现了一种活性最强的衍生物(10k)，其在活性结构关系研究中的性质与化合物2不同。 (C) 2004 Elsevier Ltd. 保留所有权利。
• 4-(3-Cyanopyridin-2-ylthio)acetoacetates in synthesis of heterocycles
  作者：L. A. Rodinovskaya、A. M. Shestopalov、A. V. Gromova

  DOI：10.1023/b:rucb.0000011877.60574.34

  日期：2003.10

  Substituted 2-amino-4-aryl-3-cyano-5-oxo-5,6-dihydro-4H-pyrano[2,3-d]pyrido[3",2":4,5]thieno[3,2-b]pyridines were synthesized by the reactions of 4-hydroxy-1H-thieno[2,3-b;4,5-b]dipyridin-2-ones with arylidenemalononitriles or by the three-component reactions of hydroxythienodipyridinones with aldehydes and malononitrile in DMF in the presence of triethylamine. Methods for syntheses of substituted

  取代的 2-amino-4-aryl-3-cyano-5-oxo-5,6-dihydro-4H-pyrano[2,3-d]pyrido[3",2":4,5]thieno[3,2 -b]吡啶是通过 4-羟基-1H-噻吩并[2,3-b;4,5-b]二吡啶-2-酮与亚芳基丙二腈的反应或羟基噻吩二吡啶酮与醛和丙二腈的三组分反应合成的在三乙胺存在下的 DMF 中。在4-(3-cyanopyridin-2-)反应的基础上,开发了取代3-烷氧基羰基-6-氨基-4-芳基-2-(3-氰基吡啶-2-基硫甲基)-4H-吡喃的合成方法。硫代)乙酰乙酸酯和亚芳基丙二腈或醛和丙二腈。4-(3-氰基吡啶-2-基硫基)乙酰乙酸乙酯和4-甲氧基亚苄基氰基硫代乙酰胺用于合成6-(吡啶-2-基硫甲基)-3-氰基吡啶-2(1H)-硫酮。
• Thienopyridine Derivatives for the Treatment and Prevention of Dengue Virus Infections
  申请人：Siga Technologies, Inc.

  公开号：US20130129677A1

  公开（公告）日：2013-05-23

  Methods and pharmaceutical compositions for treating viral infections, by administering certain thienopyridine derivative compounds in therapeutically effective amounts are disclosed. Methods of using the compounds and pharmaceutical compositions thereof are also disclosed. In particular, the treatment of viral infections such as caused by flavivirus is disclosed, i.e., including but not limited to, Dengue virus, West Nile virus, yellow fever virus, Japanese encephalitis virus, and tick-borne encephalitis virus.

  本发明揭示了使用某些噻唑吡啶衍生物化合物以治疗病毒感染的方法和制药组合物，通过以治疗有效剂量给药。同时还揭示了使用这些化合物和制药组合物的方法。具体地，揭示了治疗由黄热病毒、日本脑炎病毒、西尼罗河病毒、登革热病毒和蜱媒脑炎病毒等引起的病毒感染的方法。
• Salarian; Asadi-Eskandar; Sakhteman, Asian Journal of Chemistry, 2013, vol. 25, # 3, p. 1275 - 1278
  作者：Salarian、Asadi-Eskandar、Sakhteman、Abdi

  DOI：——

  日期：——
• 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.