2-thioxo-2,5,6,7-tetrahydro-1H-cyclopenta[b]pyridine-3-carbonitrile | 154384-01-7

• 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-2,5,6,7-tetrahydro-1H-cyclopenta[b]pyridine-3-carbonitrile
• 英文别名: 2-sulfanyl-5H,6H,7H-cyclopenta[b]pyridine-3-carbonitrile；2-sulfanylidene-1,5,6,7-tetrahydrocyclopenta[b]pyridine-3-carbonitrile
• CAS: 154384-01-7
• 化学式: C₉H₈N₂S
• mdl: MFCD02854673
• 分子量: 176.242
• InChiKey: JPCVQCHARWIKEH-UHFFFAOYSA-N

物化性质

• 沸点：
  358.8±35.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 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-2,5,6,7-tetrahydro-1H-cyclopenta[b]pyridine-3-carbonitrile 在 氢氧化钾 、 碘 作用下， 以 乙醇 为溶剂， 以73%的产率得到2,2'-bis(5,6-trimethylene-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：

  环戊酮 在 sodium methylate 、 哌啶乙酸盐 作用下， 以 甲醇 、 水 为溶剂， 反应 16.0h， 生成 2-thioxo-2,5,6,7-tetrahydro-1H-cyclopenta[b]pyridine-3-carbonitrile
  参考文献：
  名称：

  A synthesis, in silico, in vitro and in vivo study of thieno[2,3-b]pyridine anticancer analogues

  摘要：

  吡啶并噻吩[2,3-b]吡啶与TDP1结合，最佳类似物为9d，IC₅₀为0.5 μM。

  DOI：

  10.1039/c5md00245a

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。
• 2-Bromo-1-arylethylidenemalononitriles — Convenient reagents for the regioselective synthesis of fused pyridines
  作者：Vasilii A. Artyomov、Vladimir L. Ivanov、Anatolii M. Shestopalov、Victor P. Litvinov

  DOI：10.1016/s0040-4020(97)00847-8

  日期：1997.9

  subsequently involved in the Thorpe reaction. Resulting enaminoacrylonitriles form pyridine ring under base catalysis yielding thienodipyridines. According to this common scheme, functionally substituted thieno[3,2-b]pyridines, thiazolo[4,5-b]pyridines, thieno[3,2-b:4,5-b]dipyridines, their hydrogenated analogues, and pyrido[2′,3′:4,5]thieno[2,3-d]pyrimidine were synthesized.

  2-溴-1-芳基乙叉基丙二腈与共轭硫代乙腈反应生成区域选择性S烷基化产物，该产物随后可参与Thorpe反应。所得的烯氨基丙烯腈在碱催化下形成吡啶环，产生噻吩并吡啶。根据该通用方案，功能上取代的噻吩并[3,2- b ]吡啶，噻唑并[4,5- b ]吡啶，噻吩并[3,2- b：4,5- b ]二吡啶，它们的氢化类似物和吡啶基合成了[2'，3'：4,5]噻吩并[2,3- d ]嘧啶。
• [EN] METHODS AND COMPOSITIONS FOR INHIBITING HUMAN COPPER TRAFFICKING PROTEINS ATOX1 AND CCS<br/>[FR] MÉTHODES ET COMPOSITIONS D'INHIBITION DES PROTÉINES ATOX1 ET CCS IMPLIQUÉES DANS LE TRANSFERT DU CUIVRE
  申请人：UNIV CHICAGO

  公开号：WO2014116859A1

  公开（公告）日：2014-07-31

  Compositions and methods concern organic molecules that bind to human Atox1 and CCS at the copper trafficking interface of these proteins. This binding suppresses copper trafficking, which leads to inhibition of cancer cell proliferation and tumor growth. In addition to serving as an effective treatment of cancer, these organic molecules inhibit cellular copper uptake and can be used as treatment of disorders of copper metabolism such as Wilson's disease, which is characterized by copper overload, as well as wound healing.

  这些组合物和方法涉及与人类Atox1和CCS在这些蛋白质的铜转运界面结合的有机分子。这种结合抑制铜转运，导致抑制癌细胞增殖和肿瘤生长。除了作为癌症的有效治疗外，这些有机分子还抑制细胞铜摄取，可用于治疗铜代谢紊乱，如威尔逊病，其特征是铜超载，以及伤口愈合。
• 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
• SMALL MOLECULES FOR THE MODULATION OF MCL-1 AND METHODS OF MODULATING CELL DEATH, CELL DIVISION, CELL DIFFERENTIATION AND METHODS OF TREATING DISORDERS
  申请人：Dana-Farber Cancer Institute, Inc.

  公开号：EP3138838A1

  公开（公告）日：2017-03-08

  This invention relates to compounds which selectively bind to the survival protein MCL-1 with high affinity and selectivity, pharmaceutical compositions containing such compounds and the use of those compounds or compositions for modulating MCL-1 activity and for treating hyperproliferative disorders, angiogenesis disorders, cell cycle regulation disorders, autophagy regulation disorders, inflammatory disorders, and/or infectious disorders and/or for enhancing cellular engraftment and/or wound repair, as a sole agent or in combination with other active ingredients.

  本发明涉及以高亲和力和选择性与存活蛋白 MCL-1 选择性结合的化合物、含有此类化合物的药物组合物，以及使用这些化合物或组合物调节 MCL-1 活性和治疗过度增殖性疾病、血管生成疾病、细胞周期调节疾病、自噬调节疾病、炎症性疾病和/或感染性疾病和/或增强细胞移植和/或伤口修复，可作为单独制剂或与其他活性成分组合使用。