6-(pyridine-2-yl)-3-cyanopyridine-2-(1H)-thione | 118947-87-8

• 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-(pyridine-2-yl)-3-cyanopyridine-2-(1H)-thione
• 英文别名: 6-(3-pyridinyl)-3-cyanopyridine-2-(1H)-thione；6-(3-pyridyl)-3-cyano-2(1H)-pyridinethione；6-(3-Pyridyl)-3-cyanopyridine-2(1h)-thione；6-pyridin-3-yl-2-sulfanylidene-1H-pyridine-3-carbonitrile
• CAS: 118947-87-8
• 化学式: C₁₁H₇N₃S
• 分子量: 213.263
• InChiKey: PREZJTKROSTHFW-UHFFFAOYSA-N

物化性质

• 熔点：
  230-231 °C(Solv: 1-butanol (71-36-3))
• 沸点：
  379.8±52.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 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：
  80.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(pyridine-2-yl)-3-cyanopyridine-2-(1H)-thione 以79%的产率得到
  参考文献：
  名称：

  RODINOVSKAYA, L. A.;SHARANIN, YU. A.;SHESTOPALOV, A. M.;LITVINOV, V. P., XIMIYA GETEROTSIKL. SOED.,(1988) N 6, 805-812

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氰基硫代乙酰胺 、 1-(3-吡啶基)-3-(二甲氨基)-2-丙烯-1-酮 在 三乙烯二胺 作用下， 以 乙醇 为溶剂， 以40%的产率得到6-(pyridine-2-yl)-3-cyanopyridine-2-(1H)-thione
  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

• THIENO[2,3-b]PYRIDINE DERIVATIVE AND QUINOLINE DERIVATIVE, AND USE THEREOF
  申请人：The University of Tokyo

  公开号：US20190177336A1

  公开（公告）日：2019-06-13

  It is an object of the present invention to provide a compound inhibiting the binding between ALS-related mutant SOD1 and Derlin-1, a medicament comprising the compound, and a method for treating ALS by administering the medicament to a patient. More specifically, the aforementioned compound is represented by the following formula (1): wherein X represents a sulfur atom or —CH═CH—; A 1 to A 4 each independently represent a carbon atom or a nitrogen atom, and at least one of A 1 to A 4 is a nitrogen atom; R 1 represents a 1,2,3,4-tetrahydroquinolyl group (or a 3,4-dihydro-1(2H)-quinolyl group), a 3,4-dihydro-4,4-dimethyl-1(2H)-quinolyl group, a 2,3,4,5-tetrahydro-1H-1-benzazepinyl group, or a substituent represented by the following formula (2): wherein R 4 represents an unsubstituted or optionally substituted phenyl group, an unsubstituted or optionally substituted pyridyl group, or an unsubstituted or optionally substituted naphthyl group, and R 5 represents any one of a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group (optionally containing an oxygen atom and/or a double bond), or an unsubstituted or optionally substituted aromatic lower alkyl group; R 2 represents a hydrogen atom, a lower alkyl group, a lower acyl group, or an unsubstituted or optionally substituted aromatic lower alkyl group; and R 3 represents a hydrogen atom, or R 2 and R 3 may bind to each other to form a ring.

  本发明的目的是提供一种抑制ALS相关突变SOD1和Derlin-1结合的化合物，包括该化合物的药物以及通过向患者施用该药物治疗ALS的方法。具体而言，上述化合物由以下公式（1）表示：其中X表示硫原子或-CH═CH-；A1至A4分别独立表示碳原子或氮原子，且至少有一个为氮原子；R1表示1,2,3,4-四氢喹啉基（或3,4-二氢-1（2H）-喹啉基），3,4-二氢-4,4-二甲基-1（2H）-喹啉基，2,3,4,5-四氢-1H-1-苯并氮杂环基或由以下公式（2）表示的取代基：其中R4表示未取代或可选取代的苯基，未取代或可选取代的吡啶基或未取代或可选取代的萘基，而R5表示氢原子，低碳基，低烯基，低炔基（可选含氧原子和/或双键）或未取代或可选取代的芳香基低碳基中的任意一种；R2表示氢原子，低碳基，低酰基或未取代或可选取代的芳香基低碳基；而R3表示氢原子，或R2和R3可结合形成环。
• Synthesis of some new bipyridines, thieno[2,3-b]pyridines, and pyrazolo[3,4-b]pyridines
  作者：Mahmoud A. Mohamed

  DOI：10.1002/jhet.802

  日期：2012.1

  3‐hydroxy‐1‐(pyridin‐3‐yl)prop‐2‐en‐1‐one gave 6‐oxo‐[2,3′]bipyridine 5a and 6‐thioxo‐[2,3′]bipyridine 5b derivatives, respectively. Compound 5b upon treatment with different methylenes 8 gave thieno[2,3‐b]pyridines 10. Treatment of 5b with iodomethane gave bipyridine derivative 7, which cyclocondensed with hydrazines 11 to give pyrazolo[3,4‐b]pyridines 13. J. Heterocyclic Chem., (2012).

  氰基乙酰胺和氰基硫代乙酰胺与3-羟基-1-（吡啶-3-基）丙-2-烯-1-酮的钠盐进行环缩合得到6-氧代[2,3']联吡啶5a和6-硫代[[ 2,3']联吡啶5b衍生物。用不同的亚甲基8处理后的化合物5b得到噻吩并[2,3- b ]吡啶10。用碘甲烷处理5b得到联吡啶衍生物7，联吡啶衍生物7与肼11环缩合，得到吡唑并[3,4- b ]吡啶13。J.杂环化​​学。（2012）。
• Thieno[2,3-b]pyridine derivative, quinoline derivative, and use thereof
  申请人：The University of Tokyo

  公开号：US10689394B2

  公开（公告）日：2020-06-23

  A compound represented by the following formula (1) is provided: wherein X represents a sulfur atom or —CH═CH—; A1 to A4 each independently represent a carbon atom or a nitrogen atom, and at least one of A1 to A4 is a nitrogen atom; R1 represents any one of a 1,2,3,4-tetrahydroquinolyl group (or a 3,4-dihydro-1(2H)-quinolyl group), a 3,4-dihydro-4,4-dimethyl-1(2H)-quinolyl group, a 2,3,4,5-tetrahydro-1H-1-benzazepinyl group, or a substituent represented by the following formula (2): wherein R4 represents a 2,3,4-trifluorophenyl group, a 4-iodophenyl group, a 2,3-difluorophenyl group, a 3,5-difluorophenyl group, a 5-fluoro-2-methylphenyl group, a 3-pentafluorosulfanylphenyl group, a 2,6-dimethylphenyl group, a 4-benzyloxyphenyl group, a 3,5-bis(trifluoromethyl)biphenyl group, a 4-tert-butylphenyl group, a 3-methoxyphenyl group, an unsubstituted or substituted pyridyl group, or an unsubstituted or substituted naphthyl group; R5 represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group optionally containing an oxygen atom and/or a double bond, or an unsubstituted or substituted aromatic lower alkyl group; R2 represents a hydrogen atom, a lower alkyl group, a lower acyl group, or an unsubstituted or substituted aromatic lower alkyl group; and R3 represents a hydrogen atom, or R2 and R3 may bind to each other to form a ring.

  提供了下式（1）所代表的化合物： 其中X代表硫原子或-CH═CH-；A1至A4各自独立地代表碳原子或氮原子，且A1至A4中至少有一个是氮原子；R1 代表 1，2，3，4-四氢喹啉基（或 3，4-二氢-1(2H)-喹啉基）、3，4-二氢-4，4-二甲基-1(2H)-喹啉基、2，3，4，5-四氢-1H-1-苯并氮杂卓基或下式(2)所代表的取代基中的任一个： 其中 R4 代表 2,3,4-三氟苯基基团、4-碘苯基基团、2,3-二氟苯基基团、3,5-二氟苯基基团、5-氟-2-甲基苯基基团、3-五氟硫代苯基基团、2,6-二甲基苯基基团4-苄氧基苯基、3,5-双（三氟甲基）联苯基、4-叔丁基苯基、3-甲氧基苯基、未取代或取代的吡啶基或未取代或取代的萘基；R5 代表氢原子、低级烷基、低级烯基、任选含有氧原子和/或双键的低级炔基、或未取代或取代的芳香族低级烷基； R2 代表氢原子、低级烷基、低级酰基、或未取代或取代的芳香族低级烷基；以及 R3 代表氢原子，或 R2 和 R3 可相互结合形成一个环。
• 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.