6'-amino-2'-thioxo-1',2'-dihydro-3,4'-bipyridine-3',5'-dicarbonitrile | 709637-47-8

• 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'-amino-2'-thioxo-1',2'-dihydro-3,4'-bipyridine-3',5'-dicarbonitrile
• 英文别名: 2-amino-4-pyridin-3-yl-6-sulfanylidene-1H-pyridine-3,5-dicarbonitrile
• CAS: 709637-47-8
• 化学式: C₁₂H₇N₅S
• 分子量: 253.287
• InChiKey: WDUZDMCCVNRZGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  18
• 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：
  131
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6'-amino-2'-thioxo-1',2'-dihydro-3,4'-bipyridine-3',5'-dicarbonitrile 在 一水合肼 作用下， 生成 3-amino-6-hydrazino-4-pyridin-3-yl-7,7a-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile
  参考文献：
  名称：

  Synthesis, Reactions, and Antiviral Activity of 6′-Amino-2′-thioxo-1′,2′-dihydro-3,4′-bipyridine-3′,5′-dicarbonitrile

  摘要：

  Nicotinaldehyde 1 reacted with 2-cyanoethanethioamide 2 to give 2-cyano-3-pyridin-3-ylprop-2-enethioamide 3, which reacted with a second mole of 2 to give the corresponding 6'-amino-2'-thioxo-1',2'-dihydro-3,4'-bipyridine-3',5'-dicarbonitrile 6. The synthetic potentiality of compound 6 was investigated via its reaction with active halogen-containing reagents, e.g., chloroacetone, 2-chloro-3-oxobutanoate, 2-chloroacetamide, chloroaceto-nitrile, and ethyl chloroacetate, to afford the corresponding thieno[2,3-b]-pyridine derivatives. Structure elucidation of all newly synthesized heterocyclic compounds was based on the data of elemental analyses, and IR, (HNMR)-H-1, as well as mass spectra. Cytotoxicity, anti-HSV1, anti-HAV, and MBB activities were evaluated for all newly synthesized heterocyclic compounds.

  DOI：

  10.1080/10426500601087277
• 作为产物：
  描述：

  2-氰基硫代乙酰胺 、 2-cyano-3-(3'-pyridyl)acrylthioamide 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 6'-amino-2'-thioxo-1',2'-dihydro-3,4'-bipyridine-3',5'-dicarbonitrile
  参考文献：
  名称：

  Synthesis, Reactions, and Antiviral Activity of 6′-Amino-2′-thioxo-1′,2′-dihydro-3,4′-bipyridine-3′,5′-dicarbonitrile

  摘要：

  Nicotinaldehyde 1 reacted with 2-cyanoethanethioamide 2 to give 2-cyano-3-pyridin-3-ylprop-2-enethioamide 3, which reacted with a second mole of 2 to give the corresponding 6'-amino-2'-thioxo-1',2'-dihydro-3,4'-bipyridine-3',5'-dicarbonitrile 6. The synthetic potentiality of compound 6 was investigated via its reaction with active halogen-containing reagents, e.g., chloroacetone, 2-chloro-3-oxobutanoate, 2-chloroacetamide, chloroaceto-nitrile, and ethyl chloroacetate, to afford the corresponding thieno[2,3-b]-pyridine derivatives. Structure elucidation of all newly synthesized heterocyclic compounds was based on the data of elemental analyses, and IR, (HNMR)-H-1, as well as mass spectra. Cytotoxicity, anti-HSV1, anti-HAV, and MBB activities were evaluated for all newly synthesized heterocyclic compounds.

  DOI：

  10.1080/10426500601087277

文献信息

• Modifications on the Amino-3,5-dicyanopyridine Core To Obtain Multifaceted Adenosine Receptor Ligands with Antineuropathic Activity
  作者：Marco Betti、Daniela Catarzi、Flavia Varano、Matteo Falsini、Katia Varani、Fabrizio Vincenzi、Silvia Pasquini、Lorenzo di Cesare Mannelli、Carla Ghelardini、Elena Lucarini、Diego Dal Ben、Andrea Spinaci、Gianluca Bartolucci、Marta Menicatti、Vittoria Colotta

  DOI：10.1021/acs.jmedchem.9b00106

  日期：2019.8.8

  the alpha7 subtype of nAchRs, similar to the nonselective AR antagonist caffeine, taken as the reference compound. Along with the pharmacological evaluation, chemical stability of methyl 3-(((6-amino-3,5-dicyano-4-(furan-2-yl)pyridin-2-yl)sulfanyl)methyl)benzoate 10 was assessed in plasma matrices (rat and human), and molecular modeling studies were carried out to better rationalize the available structure-activity

  为了进一步研究该支架获得腺苷受体（AR）配体的潜力，合成了一系列新的氨基-3,5-二氰基吡啶（1-31），并对其进行了生物学评估。通常，进行的修饰导致化合物具有高至良好的人（h）A1AR亲和力和反向激动剂谱。尽管大多数化合物是hA1AR选择性的，但某些衍生物的作用类似于混合的hA1AR反向激动剂/ A2A和A2B AR拮抗剂。后者的化合物（9-12）显示，它们通过涉及nAchRs的alpha7亚型的机制减轻了奥沙利铂诱导的神经性疼痛，该机制类似于非选择性AR拮抗剂咖啡因，被用作参考化合物。连同药理学评估，甲基3-（（（6-氨基-3，
• SUBSTITUTED DICYANOPYRIDINES AND USE THEREOF
  申请人：Vakalopoulos Alexandros

  公开号：US20130210795A1

  公开（公告）日：2013-08-15

  The present application relates to novel substituted dicyanopyridines, to processes for their preparation, to their use for the treatment and/or prophylaxis of diseases and to their use for preparing medicaments for the treatment and/or prophylaxis of diseases, preferably for the treatment and/or prophylaxis of cardiovascular disorders.

  本申请涉及新型取代二氰基吡啶，其制备方法，它们用于治疗和/或预防疾病的用途，以及用于制备治疗和/或预防疾病的药物的用途，特别是用于治疗和/或预防心血管疾病的用途。
• SUBSTITUTED AZABICYCLIC COMPOUNDS AND THE USE THEREOF
  申请人：Nell Peter

  公开号：US20110003845A1

  公开（公告）日：2011-01-06

  The present application relates to novel substituted pyrrolopyridine, pyrazolopyridine and isoxazolopyridine derivatives, to processes for their preparation, to their use for the treatment and/or prevention of diseases and to their use for preparing medicaments for the treatment and/or prevention of diseases, preferably for the treatment and/or prevention of cardiovascular disorders.

  本申请涉及新型取代吡咯吡啶、吡唑吡啶和异氧杂吡啶衍生物，以及它们的制备方法，它们用于治疗和/或预防疾病，以及用于制备用于治疗和/或预防疾病的药物，特别是用于治疗和/或预防心血管疾病。
• 4-Heteroaryl Substituted Amino-3,5-Dicyanopyridines as New Adenosine Receptor Ligands: Novel Insights on Structure-Activity Relationships and Perspectives
  作者：Daniela Catarzi、Flavia Varano、Erica Vigiani、Sara Calenda、Fabrizio Melani、Katia Varani、Fabrizio Vincenzi、Silvia Pasquini、Natascia Mennini、Giulia Nerli、Diego Dal Ben、Rosaria Volpini、Vittoria Colotta

  DOI：10.3390/ph15040478

  日期：——

  A new set of amino-3,5-dicyanopyridines was synthesized and biologically evaluated at the adenosine receptors (ARs). This chemical class is particularly versatile, as small structural modifications can influence not only affinity and selectivity, but also the pharmacological profile. Thus, in order to deepen the structure–activity relationships (SARs) of this series, different substituents were evaluated

  合成了一组新的氨基-3,5-二氰基吡啶，并在腺苷受体 (AR) 上进行了生物学评估。这种化学类别特别通用，因为小的结构修饰不仅会影响亲和力和选择性，还会影响药理学特征。因此，为了加深该系列的构效关系（SAR），在二氰基吡啶支架的不同位置评估了不同的取代基。一般来说，本文报道的化合物显示出纳摩尔级的结合亲和力，并且与人类 (h) A 1和 A 2A AR 的相互作用比与其他亚型的相互作用更好。进行了 hAR 结构的对接研究以合理化观察到的亲和力数据。感兴趣的是化合物1和5, 它可以被认为是泛配体，因为它以相当的纳摩尔结合亲和力结合所有 ARs (A 1 AR: 1 , K i = 9.63 nM; 5 , K i = 2.50 nM; A 2A AR: 1 , K i = 21 nM ；5，Ki = 24 nM；A 3 AR：1，Ki = 52 nM；5，Ki = 25 nM；A 2B AR：1，EC
• SUBSTITUIERTE PYRROLO[2, 3-B]- UND PYRAZOLO[3, 4-B]PYRIDINE ALS ADENOSIN REZEPTOR LIGANDEN
  申请人：Bayer Schering Pharma Aktiengesellschaft

  公开号：EP2235011A1

  公开（公告）日：2010-10-06