2-thioxo-1,2,5,6,7,8,9,10-octahydrocycloocta[b]pyridine-3-carbonitrile | 154384-02-8

• 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: 2-thioxo-1,2,5,6,7,8,9,10-octahydrocycloocta[b]pyridine-3-carbonitrile
• 英文别名: 2-sulfanyl-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine-3-carbonitrile
• CAS: 154384-02-8
• 化学式: C₁₂H₁₄N₂S
• mdl: MFCD02854683
• 分子量: 218.323
• InChiKey: KJZGSJGINZZEDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  2-thioxo-1,2,5,6,7,8,9,10-octahydrocycloocta[b]pyridine-3-carbonitrile 在 氢氧化钾 、 碘 作用下， 以 乙醇 为溶剂， 以82%的产率得到2,2'-bis(5,6-hexamethylene-3-cyano-2-pyridyl) disulfide
  参考文献：
  名称：

  5,6-聚亚甲基-3-氰基吡啶-2(1H)-硫酮和基于它们的稠合杂环的区域选择性合成

  摘要：

  2-羟基亚甲基环戊烷-1-酮或-环辛烷-1-酮钠盐与氰硫代乙酰胺缩合得到5,6-聚亚甲基-3-氰基吡啶-2(1H)-硫酮，其在硫原子上被卤代烷区域选择性烷基化。3-氰基吡啶-2(1H)-硫酮和2-烷硫基-3-氰基吡啶的衍生物用于区域选择性合成取代杂环：3-氨基噻吩并[2,3-b]吡啶、吡啶并[2,3∶2'、 3']噻吩并[4,5-d]嘧啶和吡啶并[2,3∶2',3']噻吩并[4,5-d]恶嗪。

  DOI：

  10.1007/bf01169725
• 作为产物：
  描述：

  环辛酮 在 乙醇 、 sodium 作用下， 以 乙醚 、 乙醇 、 溶剂黄146 为溶剂， 反应 3.0h， 生成 2-thioxo-1,2,5,6,7,8,9,10-octahydrocycloocta[b]pyridine-3-carbonitrile
  参考文献：
  名称：

  5,6-聚亚甲基-3-氰基吡啶-2(1H)-硫酮和基于它们的稠合杂环的区域选择性合成

  摘要：

  2-羟基亚甲基环戊烷-1-酮或-环辛烷-1-酮钠盐与氰硫代乙酰胺缩合得到5,6-聚亚甲基-3-氰基吡啶-2(1H)-硫酮，其在硫原子上被卤代烷区域选择性烷基化。3-氰基吡啶-2(1H)-硫酮和2-烷硫基-3-氰基吡啶的衍生物用于区域选择性合成取代杂环：3-氨基噻吩并[2,3-b]吡啶、吡啶并[2,3∶2'、 3']噻吩并[4,5-d]嘧啶和吡啶并[2,3∶2',3']噻吩并[4,5-d]恶嗪。

  DOI：

  10.1007/bf01169725

文献信息

• 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。
• Thieno[2,3-b]pyridine derivatives are potent anti-platelet drugs, inhibiting platelet activation, aggregation and showing synergy with aspirin
  作者：Naif K. Binsaleh、Catherine A. Wigley、Kathryn A. Whitehead、Michelle van Rensburg、Johannes Reynisson、Lisa I. Pilkington、David Barker、Sarah Jones、Nina C. Dempsey-Hibbert

  DOI：10.1016/j.ejmech.2017.11.014

  日期：2018.1

  assessed for in vitro anti-platelet activity; all derivatives showed effects on both platelet activation and aggregation, and showed synergy with ASA. Some compounds demonstrated greater activity when compared to clopidogrel. These compounds, therefore, represent potential novel P2Y12 inhibitors for improved treatment for patients.

  抑制血小板功能的药物通常用于预防患有急性冠状动脉综合征（ACS）或有中风风险的患者的血凝块形成。噻吩并[3,2- c ]吡啶类治疗药物（最普遍使用的是氯吡格雷）靶向P2Y 12受体，并经常与乙酰水杨酸（ASA）结合使用。评估了六种噻吩并[2,3- b ]吡啶的体外抗血小板活性。所有衍生物均显示出对血小板活化和聚集的作用，并显示出与ASA的协同作用。与氯吡格雷相比，某些化合物具有更高的活性。因此，这些化合物代表了潜在的新型P2Y 12 抑制剂以改善患者的治疗。
• Substituted 4-(3-Cyanopyridin-2-ylthio)acetoacetates: New Convenient Reagents for the Synthesis of Heterocycles
  作者：Lyudmila Rodinovskaya、Anatoliy Shestopalov、Anna Gromova、Alexander Shestopalov

  DOI：10.1055/s-2006-942433

  日期：——

  Polyfunctional 4-(3-cyanopyridin-2-ylthio)acetoacetates were used in the synthesis of 4-hydroxy-1H-thieno[2,3-b:4,5-b]dipyridin-2-ones. The latter were used in reactions with arylidene-malononitriles or in three-component reactions with aldehydes and malononitrile to give 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. Utilizing 4-(3-cyanopyridin-2

  多官能团 4-(3-cyanopyridin-2-ylthio)acetoacetates 用于合成 4-hydroxy-1H-thieno[2,3-b:4,5-b]dipyridin-2-ones。后者用于与亚芳基-丙二腈的反应或与醛和丙二腈的三组分反应，得到 2-amino-4-aryl-3-cyano-5-oxo-5,6-dihydro-4H-pyrano[2, 3-d]吡啶并[3',2':4,5]噻吩并[3,2-b]吡啶。利用 4-(3-cyanopyridin-2-ylthio)acetoacetates 和亚芳基丙二腈或醛和丙二腈，我们开发了一种合成取代的 3-alkoxycarbonyl-6-amino-4-aryl-2-(3-cyanopyridin-2-基硫甲基）-4H-吡喃。取代的 4-(3-cyanopyridin-2-ylthio)acetoacetates 与水合肼反应生成取代的
• Synthesis and antiproliferative activity of 2-chlorophenyl carboxamide thienopyridines
  作者：Michelle van Rensburg、Euphemia Leung、Natalie A. Haverkate、Chatchakorn Eurtivong、Lisa I. Pilkington、Jóhannes Reynisson、David Barker

  DOI：10.1016/j.bmcl.2016.12.009

  日期：2017.1

  3-Amino-2-arylcarboxamide-thieno[2,3-b]pyridines are a known class of antiproliferative compounds with activity against the phospholipase C enzyme. To further investigate the structure activity relationships of these derivatives a series of analogues were prepared modifying key functional groups. It was determined that modification of the 3-amino and 2-aryl carboxamide functionalities resulted in complete elimination of activity, whilst modification at C-5 allowed compounds of greater activity to be prepared. (C) 2016 Elsevier Ltd. All rights reserved.
• Inhibition of eEF2-K by thieno[2,3-b]pyridine analogues
  作者：Jeffrey W. Lockman、Matthew D. Reeder、Kazuyuki Suzuki、Kirill Ostanin、Ryan Hoff、Leena Bhoite、Harry Austin、Vijay Baichwal、J. Adam Willardsen

  DOI：10.1016/j.bmcl.2010.02.005

  日期：2010.4

  Several series of thieno[2-3-b]pyridine analogues were synthesized and screened for inhibitory activity against eukaryotic elongation factor-2 kinase (eEF2-K). Modifications around several regions of the lead molecules were made, with a ring fusion adjacent to the nitrogen on the thienopyridine core being critical for activity. The most active compound 34 shows an IC(50) of 170 nM against eEF2-K in vitro. (C) 2010 Elsevier Ltd. All rights reserved.