3-cyano-6-phenyl-4-(thiophen-2'-yl)-2(1H)-pyridone | 59851-02-4

• 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: 3-cyano-6-phenyl-4-(thiophen-2'-yl)-2(1H)-pyridone
• 英文别名: 3-cyano-4-(2'-thienyl)-6-phenyl-2-pyridone；2-oxo-6-phenyl-4-(2-thienyl)-1,2-dihydro-3-pyridinecarbonitrile；2-oxo-6-phenyl-4-thiophen-2-yl-1H-pyridine-3-carbonitrile
• CAS: 59851-02-4
• 化学式: C₁₆H₁₀N₂OS
• 分子量: 278.334
• InChiKey: BXXROIDYNDJFMR-UHFFFAOYSA-N

物化性质

• 熔点：
  301-303 °C(Solv: N,N-dimethylformamide (68-12-2))
• 沸点：
  529.1±50.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-cyano-6-phenyl-4-(thiophen-2'-yl)-2(1H)-pyridone 在 氨 、 potassium hydroxide 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 0.5h， 生成 3-cyano-1-(β-D-glucopyranosyl)-6-phenyl-4-(thiophen-2'-yl)-2-pyridone
  参考文献：
  名称：

  微波辅助合成2（1H）-吡啶酮及其糖苷作为细胞增殖抑制剂。

  摘要：

  一系列新的取代的2-（1 ħ） -吡啶酮（4A-I ）和它们的糖苷（5，图6A-E ）中制备作为针对白血病潜在剂（HL-60）细胞。葡糖苷（5，图6A-E ）用三个独立的方法来合成。微波协议是一种生态学新方法，用于合成目标化合物。使用一维和二维NMR光谱确认了新产品的结构。发现在体外暴露于4位被2-噻吩基或2-（三氟甲基）苯基取代的吡啶酮具有很高的抗增殖活性。特别是3-cyano-4-（thien-2'-yl）-6-（4''-chlorophenyl）-2（1 H）-吡啶酮（4c）及其糖苷类似物（6c）的活性最高。

  DOI：

  10.1080/15257770.2010.551646
• 作为产物：
  描述：

  3-cyano-6-phenyl-4-(2-thienyl)pyridin-2(1H)-thione 在 potassium tert-butylate 、 碘 作用下， 以 叔丁醇 为溶剂， 反应 48.0h， 生成 3-cyano-6-phenyl-4-(thiophen-2'-yl)-2(1H)-pyridone
  参考文献：
  名称：

  Elgemeie, Galal Eldin Hamza; Zohdi, Hussein Fouad; Sherif, Sherif Mourad, Phosphorus, Sulfur and Silicon and the Related Elements, 1990, vol. 54, # 1/4, p. 215 - 219

  摘要：

  DOI：

文献信息

• Synthesis and anti-proliferative activity of pyridine <i>O</i>-galactosides and 4-fluorobenzoyl analogues
  作者：Shaikha S. Alneyadi、Ihsan A. Shehadi、Ibrahim M. Abdou

  DOI：10.1515/hc-2015-0125

  日期：2015.10.1

  Pyridine O-galactosides 3, 4, and 2-(4′-fluorobenzoyloxy)pyridine derivatives 5 were prepared by simple nucleophilic substitution reactions. These nucleosides were studied as anti-proliferating agents of human promyelotic leukemia (HL-60) cells. Compound 5a shows the highest anti-proliferative activity (77% at 100 μm) among the synthesized compounds.

  通过简单的亲核取代反应制备了吡啶O-半乳糖苷3、4和2-(4′-氟苯甲酰氧)吡啶衍生物5。这些核苷类化合物被研究作为人类早幼粒细胞白血病（HL-60）细胞的抗增殖剂。化合物5a在合成化合物中表现出最高的抗增殖活性（100 μm下为77%）。

• Efficient Approach to the Synthesis of Ethyl 3-Amino-4,6-diarylfuro[2,3-<i>b</i>]pyridine-2-carboxylate
  作者：Hetal C. Shah、Vaishali H. Shah、Nirmal D. Desai

  DOI：10.1080/00397910902730986

  日期：2009.7.29

  Abstract Novel ethyl 3-amino-4,6-diarylfuro[2,3-b]pyridine-2-carboxylate were synthesized by Thorpe–Ziegler cyclization using solid–liquid phase-transfer catalysis conditions.

  摘要 在固-液相转移催化条件下，通过Thorpe-Ziegler 环化反应合成了新型3-氨基-4,6-二芳基呋喃[2,3-b]吡啶-2-羧酸乙酯。
• Compounds for inhibiting beta-amyloid production and methods of identifying the compounds
  申请人：Mullan J. Michael

  公开号：US20060188938A1

  公开（公告）日：2006-08-24

  Provided are compounds useful for treating diseases associated with a cerebral accumulation of Alzheimer's amyloid, such as Alzheimer's disease. Also provided are methods for screening for such compounds, by measuring capacitative calcium entry in cells which optionally overexpress APP or a fragment thereof. Also provided are methods of treating or reducing the risk of developing β-amyloid production, β-amyloid deposition, β-amyloid neurotoxicity (including abnormal hyperphosphorylation of tau) and microgliosis associated with cerebral accumulation of Alzheimer's amyloid by administering therapeutically effective amounts of compounds which decrease β-amyloid production and capacitative calcium entry in cells. Further provided are methods for diagnosing diseases associated with cerebral accumulation of Alzheimer's amyloid in animals or humans by administering diagnostically effective amounts of compounds which inhibit capacitative calcium entry in cells.

  提供了对治疗与阿尔茨海默病相关的脑部淀粉样蛋白沉积疾病（如阿尔茨海默病）有用的化合物。还提供了筛选此类化合物的方法，通过测量细胞中的电容性钙离子入流，该细胞可选择过表达APP或其片段。还提供了通过给予治疗有效量的化合物来治疗或降低β-淀粉样蛋白产生、β-淀粉样蛋白沉积、β-淀粉样蛋白神经毒性（包括tau异常的超磷酸化）和与阿尔茨海默病相关的微胶质细胞病的风险的方法，这些化合物降低细胞中的β-淀粉样蛋白产生和电容性钙离子入流。此外，还提供了通过给予诊断有效量的化合物来诊断动物或人类中与阿尔茨海默病相关的脑部淀粉样蛋白沉积疾病的方法，这些化合物抑制细胞中的电容性钙离子入流。
• Compounds and Combinations Thereof for Inhibiting Beta-Amyloid Production and Methods of Use Thereof
  申请人：Paris Daniel

  公开号：US20080058330A1

  公开（公告）日：2008-03-06

  Provided are compounds which can be used in combination for treating diseases associated with a condition associated with cerebral accumulation of Alzheimer's amyloid, such as Alzheimer's disease. Also provided are methods of treating or reducing the risk of developing β-amyloid production, β-amyloid deposition, β-amyloid neurotoxicity (including abnormal hyperphosphorylation of tau) and microgliosis associated with cerebral accumulation of Alzheimer's amyloid by administering therapeutically effective amounts of compounds which in combination can decrease β-amyloid production and capacitative calcium entry in cells. Further provided are methods for diagnosing diseases associated with cerebral accumulation of Alzheimer's amyloid in animals or humans by administering diagnostically effective amounts of the compounds.

  提供了一些化合物，可以组合使用来治疗与阿尔茨海默病淀粉样蛋白相关的疾病，如阿尔茨海默病。还提供了一种方法，通过给予治疗有效量的化合物组合来减少β-淀粉样蛋白的产生和细胞中的电容性钙离子进入，从而治疗或降低发生β-淀粉样蛋白产生、β-淀粉样蛋白沉积、β-淀粉样蛋白神经毒性（包括tau异常过度磷酸化）和与阿尔茨海默病淀粉样蛋白相关的微胶质病变。此外，还提供了一种方法，通过给予诊断有效量的化合物来诊断动物或人类中与阿尔茨海默病淀粉样蛋白相关的疾病。
• Compounds for Inhibiting Beta-Amyloid Production and Methods of Identifying the Compounds
  申请人：Mullan Michael J.

  公开号：US20100215735A1

  公开（公告）日：2010-08-26

  Provided are compounds useful for treating diseases associated with a cerebral accumulation of Alzheimer's amyloid, such as Alzheimer's disease. Also provided are methods for screening for such compounds, by measuring capacitative calcium entry in cells which optionally overexpress APP or a fragment thereof. Also provided are methods of treating or reducing the risk of developing β-amyloid production, β-amyloid deposition, β-amyloid neurotoxicity (including abnormal hyperphosphorylation of tau) and microgliosis associated with cerebral accumulation of Alzheimer's amyloid by administering therapeutically effective amounts of compounds which decrease β-amyloid production and capacitative calcium entry in cells. Further provided are methods for diagnosing diseases associated with cerebral accumulation of Alzheimer's amyloid in animals or humans by administering diagnostically effective amounts of compounds which inhibit capacitative calcium entry in cells.

  提供了一些化合物，可用于治疗与阿尔茨海默氏淀粉样物质在大脑中积累有关的疾病，如阿尔茨海默病。还提供了筛选这些化合物的方法，通过测量在细胞中的电容性钙离子进入，这些细胞可以选择性地过表达APP或其片段。还提供了通过给予治疗有效量的化合物来治疗或降低发生β-淀粉样物质产生、β-淀粉样物质沉积、β-淀粉样物质神经毒性（包括tau异常过磷酸化）和与阿尔茨海默氏淀粉样物质在大脑中积累有关的小胶质细胞增生的风险的方法，这些化合物可以减少β-淀粉样物质产生和细胞中的电容性钙离子进入。此外，还提供了通过给动物或人体内给予诊断有效量的化合物来诊断与阿尔茨海默氏淀粉样物质在大脑中积累有关的疾病的方法，这些化合物可以抑制细胞中的电容性钙离子进入。