4-(furan-2-yl)-2-oxo-6-phenyl-1,2-dihydropyridine-3-carbonitrile | 77607-74-0

• 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: 4-(furan-2-yl)-2-oxo-6-phenyl-1,2-dihydropyridine-3-carbonitrile
• 英文别名: AK-968/41024707；4-(2-furyl)-2-oxo-6-phenyl-1,2-dihydro-3-pyridinecarbonitrile；4-(2-Furyl)-2-hydroxy-6-phenylnicotinonitrile；4-(furan-2-yl)-2-oxo-6-phenyl-1H-pyridine-3-carbonitrile
• CAS: 77607-74-0
• 化学式: C₁₆H₁₀N₂O₂
• 分子量: 262.268
• InChiKey: UWZPYKADXQTBEN-UHFFFAOYSA-N

物化性质

• 熔点：
  301-302 °C(Solv: 1,4-dioxane (123-91-1))
• 沸点：
  502.8±50.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 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：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(furan-2-yl)-2-oxo-6-phenyl-1,2-dihydropyridine-3-carbonitrile 在 氢氧化钾 、 氨 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 生成 4-Furan-2-yl-2-oxo-6-phenyl-1-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-1,2-dihydro-pyridine-3-carbonitrile
  参考文献：
  名称：

  Synthesis ofN-Glycosylated Pyridines as New Antiviral Agents

  摘要：

  A series of 3-cyanopyridine glycosides have been synthesized and evaluated for their inhibitory activity against human immunodeficiency virus (HIV) replication in MT-4 cells. Among the 3-cyanopyridine glycosides 6-(p-methylphenyl) and 6-(p-aminophenyl) were the most selective inhibitors of HIV replication.

  DOI：

  10.1080/15257779508010701
• 作为产物：
  描述：

  3-cyano-4-(2'-furyl)-6-phenylpyridinethione 在 氢氧化钾 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 4-(furan-2-yl)-2-oxo-6-phenyl-1,2-dihydropyridine-3-carbonitrile
  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 of new substituted pyridine derivatives as potent anti-liver cancer agents through apoptosis induction: In vitro, in vivo, and in silico integrated approaches
  作者：Ahmed T.A. Boraei、Elsayed H. Eltamany、Ibrahim A.I. Ali、Sara M. Gebriel、Mohamed S. Nafie

  DOI：10.1016/j.bioorg.2021.104877

  日期：2021.6

  Liver cancer is the most common type of cancer in many countries. New studies and statistics show rising liver cancer worldwide, so it is essential to seek new agents for this type of cancer. PIM1 has an attractive target in the discovery of cancer medications as it is very much expressed in a variety of malignancies and influences such as tumorigenesis, cell cycle progression, cellular proliferation

  肝癌是许多国家最常见的癌症类型。新的研究和统计数据显示，全球肝癌呈上升趋势，因此寻找治疗此类癌症的新药物至关重要。PIM1 在癌症药物的发现中具有吸引人的目标，因为它在多种恶性肿瘤和影响（例如肿瘤发生、细胞周期进程、细胞增殖、细胞凋亡和细胞迁移）中大量表达。因此，合成了一系列吡啶酮和吡啶-酰胺并测试了抗肝癌活性。 在合成策略中，4,6-二芳基-3-氰基-2-吡啶酮3a-n使用一锅四组分合成方法合成。对 4,6-diphenyl-3-cayno-2-pyridone 3a进行结构修饰以增强活性。在K 2 CO 3存在下烷基化得到O-烷基化产物4-6。合成乙酰氧基酰肼7并环化成 1,3,4-恶二唑硫酮8，后者在硫上烷基化得到10。采用叠氮偶联法将2-(吡啶-2-基氧基)乙酰肼7与不同的胺和氨基酸酯偶联得到产物12a-e和13a-b。将合成的衍生物进行对HepG2和THLE-2细胞，细胞毒性化合
• Synthesis of Pyrazolo[3,4-<i>b</i>]Pyridine and Pyrido[2′,3′:3,4]Pyrazolo [1,5-<i>a</i>]Pyrimidine Derivatives
  作者：Mervat M. El-Enany、Salwa E. M. El-Meligie、Nadia A. Abdou、Hala B. El-Nassan

  DOI：10.3184/030823410x12811125049438

  日期：2010.8

  The synthesis of two series of 1-phenyl and 1H-pyrazolo[3,4-b]pyridine is described. Thus, reacting 5-amino-1-phenylpyrazole with chalcone analogues gave 4,6-diarylpyrazolo[3,4-b]pyridine derivatives. While, reacting the same starting material with benzylidene derivatives of ethyl cyanoacetate and malononitrile resulted in 4-oxo and 4-aminopyrazolo[3,4-b]pyridine derivatives, respectively. The synthesis

  描述了1-苯基和1H-吡唑并[3,4-b]吡啶两个系列的合成。因此，5-氨基-1-苯基吡唑与查耳酮类似物反应得到4,6-二芳基吡唑并[3,4-b]吡啶衍生物。同时，将相同的原料与氰乙酸乙酯和丙二腈的亚苄基衍生物反应分别产生4-氧代和4-氨基吡唑并[3,4-b]吡啶衍生物。还描述了从吡啶开始合成 3-氨基-4,6-二芳基吡唑并[3,4-b]吡啶。因此，4,6-二芳基吡啶酮衍生物的氯化以及它们随后与肼水合物的环化得到3-氨基-4,6-二芳基吡唑并[3,4-b]吡啶。后一种化合物与乙酰丙酮、乙氧基亚甲基氰基乙酸乙酯和查耳酮类似物反应得到三环吡啶并[2',3':3,4]吡唑并[1,5-a]嘧啶。
• 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。