4-(4-chlorophenyl)-6-oxo-1,6-dihydro-[2,2' -bipyridine]-5-carbonitrile | 906652-90-2

• 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-(4-chlorophenyl)-6-oxo-1,6-dihydro-[2,2' -bipyridine]-5-carbonitrile
• 英文别名: 4-(4-chlorophenyl)-2-oxo-6-pyridin-2-yl-1H-pyridine-3-carbonitrile
• CAS: 906652-90-2
• 化学式: C₁₇H₁₀ClN₃O
• 分子量: 307.739
• InChiKey: NTMOJASHOMIATH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 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：
  65.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-chlorophenyl)-6-oxo-1,6-dihydro-[2,2' -bipyridine]-5-carbonitrile 在 吡啶 、 tetraphosphorus decasulfide 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 3-amino-4-(4-chlorophenyl)-6-(pyridin-2-yl)thieno[2,3-b]pyridine-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Preparation of Some Fused Pyridopyrimidine and Pyridothienotriazine Derivatives for Biological Evaluation

  摘要：

  Compounds 2 and 9 were formed using 3-(4-chloro-phenyl)-1-pyridin-2-yl propenone (1) and malononitrile or ethyl cyanoacetate, respectively. The pyridine derivative 2 was in turn used as a precursor for the preparation of some pyridopyrimidine and fused pyridopyrimidine derivatives 3-8. On the other hand, the pyridine derivative 9 was used for the preparation of thienopyridine derivatives 11 and 12. Nitrozation of compound 12 afforded pyridothienotriazine derivative 13. Some of the prepared products showed potent antimicrobial activity.

  DOI：

  10.1080/104265090968118
• 作为产物：
  描述：

  氰乙酸乙酯 、 3-(4-氯苯基)-1-(吡啶-2-基)丙-2-烯-1-酮 在 乙酸铵 、 溶剂黄146 作用下， 反应 6.0h， 以80%的产率得到4-(4-chlorophenyl)-6-oxo-1,6-dihydro-[2,2' -bipyridine]-5-carbonitrile
  参考文献：
  名称：

  Preparation of Some Fused Pyridopyrimidine and Pyridothienotriazine Derivatives for Biological Evaluation

  摘要：

  Compounds 2 and 9 were formed using 3-(4-chloro-phenyl)-1-pyridin-2-yl propenone (1) and malononitrile or ethyl cyanoacetate, respectively. The pyridine derivative 2 was in turn used as a precursor for the preparation of some pyridopyrimidine and fused pyridopyrimidine derivatives 3-8. On the other hand, the pyridine derivative 9 was used for the preparation of thienopyridine derivatives 11 and 12. Nitrozation of compound 12 afforded pyridothienotriazine derivative 13. Some of the prepared products showed potent antimicrobial activity.

  DOI：

  10.1080/104265090968118

文献信息

• Fe3O4@SiO2@(CH2)3-urea-thiourea: A novel hydrogen-bonding and reusable catalyst for the construction of bipyridine-5-carbonitriles via a cooperative vinylogous anomeric based oxidation
  作者：Fatemeh Karimi、Meysam Yarie、Mohammad Ali Zolfigol

  DOI：10.1016/j.mcat.2020.111201

  日期：2020.12

  elemental mapping analysis. The catalytic performance of the novel hydrogen-bonding catalyst was appropriately probed through the multicomponent preparation of bipyridine-5-carbonitriles via a cooperative vinylogous anomeric based oxidation (CVABO) mechanism in the absence of any solvent. The novel hydrogen-bonding nanomagnetic catalyst can readily be regained and reused four times without appreciable

  制备了Fe 3 O 4 @SiO 2 @（CH 2）3-脲硫脲作为新型的氢键可回收纳米磁性催化剂，并通过透射电子显微镜（TEM），热重分析/导数热重分析（TGA / DTG）证实了其结构。 ），振动样品磁力计（VSM），傅立叶变换红外（FT-IR）光谱，场发射扫描电子显微镜（FESEM），能量色散光谱（EDS）和元素图分析。新型氢键催化剂的催化性能可以通过联吡啶5-腈的多组分制备进行考察。在不存在任何溶剂的情况下，基于乙烯基异氰酸酯的协同氧化（CVABO）机理。新型氢键结合的纳米磁性催化剂可以很容易地获得并重复使用四次，而不会明显破坏催化效率。
• Synthesis and antitumor evaluation of some new thiazolopyridine, nicotinonitrile, pyrazolopyridine, and polyhydroquinoline derivatives using ceric ammonium nitrate as a green catalyst
  作者：Reham R. Raslan、Sadia A. Hessein、Sawsan A. Fouad、Nadia A. M. Shmiess

  DOI：10.1002/jhet.4423

  日期：2022.5

  A novel series of thiazolo[5,4-b]pyridine, polysubstituted pyridines, pyrazolo [3,4-b] pyridine-5-carbonitriles, and polyhydroquinoline were synthesized via one-pot reaction of 2-iminothiazolidin-5-one, acetyl pyridine, pyrazolone, and/or cyclohexanone with various aldehydes, some active methylene and ammonium acetate in the presence of ceric ammonium nitrate (CAN). The resulting compounds were generated

  通过 2-亚氨基噻唑烷-5-酮、乙酰基的一锅反应合成了一系列新型噻唑并[5,4 - b ]吡啶、多取代吡啶、吡唑并[3,4- b ]吡啶-5-甲腈和聚氢喹啉在硝酸铈铵 (CAN) 存在下，吡啶、吡唑啉酮和/或环己酮与各种醛、一些活性亚甲基和乙酸铵。所得化合物在短时间内以高产率生成，并使用 IR、1 H NMR、13 C-NMR 和质谱确认了新化合物的结构。体外测试了 15 种物质对 HePG-2 和 Caco-2 细胞系的细胞毒活性。抗肿瘤试验结果证实喹啉12d化合物对两种接近于多柔比星的细胞系具有更高的细胞毒活性，多柔比星被用作标准抗癌药物。此外，12c化合物对 2 细胞系具有更有效的抗肿瘤作用。而化合物1对 Caco-2 表现出中等活性。另一方面，大多数测试化合物对这两种细胞系表现出中度至低度的细胞毒活性。根据结果​​，一些新合成的衍生物显示出优异的抗肿瘤活性，使其可用于生物医学应用。
• Synthesis and biological evaluation of 2-oxonicotinonitriles and 2-oxonicotinonitrile based nucleoside analogues
  作者：Reham A.I. Abou-Elkhair、Ahmed H. Moustafa、Abdelfattah Z. Haikal、Ahmed M. Ibraheem

  DOI：10.1016/j.ejmech.2013.12.055

  日期：2014.3

  emergence of new pathogens highlight the need for developing new therapeutic agents. We focused on 2-oxonicotinonitrile (2-ONN) as derivative of the natural product 2-pyridinone.1 Herein, we describe the synthesis of 2-ONNs bearing two aryl groups, which we coupled with organohalides, including three glycosyl bromides, to prepare the nucleoside analogues. Coupling occurred mostly at the 2-ONN ring nitrogen

  耐药性和新病原体的出现突出了开发新治疗剂的必要性。我们专注于 2-氧代烟腈 (2-ONN) 作为天然产物 2-吡啶酮的衍生物。1在此，我们描述了带有两个芳基的 2-ONN 的合成，我们将其与有机卤化物（包括三种糖基溴化物）偶联以制备核苷类似物。偶联主要发生在 2-ONN 环氮上以产生目标目标，在少数情况下，它发生在 2-氧代位上，产生O-烷基化产物。游离 2-ONN 及其乙酰化核苷针对多种病毒进行了测试。核苷类似物2a Ac表现出良好的抗 SARS-CoV 和抗甲型流感（H 5 N 1） 活动。此外，7b对革兰氏阳性细菌枯草芽孢杆菌具有良好的活性。
• An efficient synthesis of 4,6‐diarylnicotinonitrile‐acetamide hybrids via 1,2,3‐triazole linker as multitarget microbial inhibitors
  作者：Hassan A. El‐Sayed、Ahmed H. Moustafa、Asmaa A. Masry、Atef M. Amer、Samar M. Mohammed

  DOI：10.1002/jhet.4381

  日期：2022.2

  H2O/tetrahydrofuran (THF) was utilized for the synthesis of target molecules 6a-l. Triazoles 6c, d, f, and 6i have highly activity against the four pathogenic bacteria (Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis, and Staphylococcus aureus) and two pathogenic fungi (Candida albicans and Aspergillus flavus) with minimum inhibitory concentration (MIC) in between 0.5 and 4 μg/ml for bacteria

  描述了一种用于设计和合成新型烟腈-1,2,3-三唑-乙酰胺杂化物系列的有效且智能的方法。合成方法开始于通过在温和的碱性催化剂（碳酸钾）下用炔丙基溴对 2-氧代烟腈进行炔基化制备乙炔衍生物。在 H 2 O/四氢呋喃 (THF) 中，在催化 Cu(I) 存在下，炔烃2a-f和叠氮基乙酰胺3-5的简单点击环加成反应用于合成目标分子6a-l。三唑类6c、d、f和6i对四种病原菌具有高度活性（大肠杆菌、铜绿假单胞菌、枯草芽孢杆菌和金黄色葡萄球菌）和两种病原真菌（白色念珠菌和黄曲霉），细菌的最低抑菌浓度 (MIC) 介于 0.5 和 4 μg/ml 之间，真菌的最低抑菌浓度 (MIC) 介于 0.5 和 8 μg/ml 之间.
• Bioevaluation of synthetic pyridones as dual inhibitors of α‐amylase and α‐glucosidase enzymes and potential antioxidants
  作者：Faiza Saleem、Khalid Mohammed Khan、Nisar Ullah、Musa Özil、Nimet Baltaş、Shehryar Hameed、Uzma Salar、Abdul Wadood、Ashfaq Ur Rehman、Mukesh Kumar、Muhammad Taha、Syed Moazzam Haider

  DOI：10.1002/ardp.202200400

  日期：2023.1

  Herein, a library of novel pyridone derivatives 1–34 was designed, synthesized, and evaluated for α-amylase and α-glucosidase inhibitory as well as antioxidant activities. Pyridone derivatives 1–34 were synthesized via a one-pot multi-component reaction of variously substituted aromatic aldehydes, acetophenone, ethyl cyanoacetate, and ammonium acetate in absolute ethanol. Synthetic compounds 1–34 were

  在此，设计、合成了一个新型吡啶酮衍生物1-34库，并评估了 α-淀粉酶和 α-葡萄糖苷酶抑制以及抗氧化活性。吡啶酮衍生物1-34通过各种取代的芳香醛、苯乙酮、氰基乙酸乙酯和乙酸铵在无水乙醇中的一锅多组分反应合成。通过不同的光谱技术对合成化合物1-34进行了结构表征。大多数测试化合物显示出比标准阿卡波糖（IC 50  = 14.87 ± 0.16 µM）更有希望的抑制潜力，但发现化合物13和12是最有效的化合物，IC 50针对α-淀粉酶和α-葡萄糖苷酶的值分别为 9.20 ± 0.14 µM 和 3.05 ± 0.18 µM。 在 DPPH 自由基清除活性 中，与对照丁基化羟基甲苯 (BHT)（IC 50 = 66.50 ± 0.36 µM）相比，化合物1–34在 IC 50 = 96.50 ± 0.45 至 189.98 ± 1.00 µM范围内也显示出适度的抗氧化潜力。此外，所有合成衍生