4-(4-methoxyphenyl)-2-oxo-6-(thiophen-2-yl)-1,2-dihydropyridine-3-carbonitrile | 120238-97-3

• 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-methoxyphenyl)-2-oxo-6-(thiophen-2-yl)-1,2-dihydropyridine-3-carbonitrile
• 英文别名: 4-(4-methoxyphenyl)-2-oxo-6-(thien-2-yl)-1,2-dihydropyridine-3-carbonitrile；4-(4-methoxyphenyl)-2-oxo-6-(thiophene-2-yl)-1,2-dihydropyridine-3-carbonitrile；3-cyano-4-(4-methoxyphenyl)-6-(2-thienyl)-2(1H)-pyridinone；4-(4-methoxyphenyl)-2-oxo-6-thiophen-2-yl-1H-pyridine-3-carbonitrile
• CAS: 120238-97-3
• 化学式: C₁₇H₁₂N₂O₂S
• 分子量: 308.36
• InChiKey: CLROQEXHVBQCSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  90.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-methoxyphenyl)-2-oxo-6-(thiophen-2-yl)-1,2-dihydropyridine-3-carbonitrile 在 sodium acetate 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 7-(4-Methoxyphenyl)-3-methyl-5-thiophen-2-yl-[1,2,4]triazolo[4,3-a]pyridine-8-carbonitrile
  参考文献：
  名称：

  A facile synthesis of some 3-cyano-1,4,6-trisubstituted-2(1H)-pyridinones and their biological evaluation as anticancer agents

  摘要：

  The synthesis of some new 3-cyano-1,4,6-trisubstituted-2(1H)-pyridinones supported with various pharmacophores and functionalities at positin-1 is described. The in vitro anticancer activity of 24 of the newly synthesized compounds was evaluated according to the protocol of the NCI in vitro disease-oriented human cells screening panel assay. The results revealed that five compounds 4a-c, 7b, and 12b were able to display moderate antitumor potential against some of the tested subpanel tumor cell lines at the GI(50) and TGI levels, however, with marginal or no cytotoxic (LC(50)) activity. The obtained data suggested that better antitumor activity was linked to derivatives with either 4-bromophenyl or 3,4-dimethoxyphenyl moieties, together with a 1-methyl-1H-pyrrol-2-yl counter part at positions 6 and 4, respectively. Consequently, the 3-cyano-4-(1-methyl-1H-pyrrol-2-yl)-6-(4-bromophenyl or 3,4-dimethoxyphenyl)-2(1H)-pyridinones 4a and 4b, could be considered as the most active members identified in this investigation as evidenced from their relative higher growth inhibitory (GI(50) (MG-MID) 77.6 and 67.6 mu M, respectively) and cytostatic (TGI (MG-MID) 85.1 and 95.5 mu M, respectively) activities, when compared with the substituted thiocarbamoyl analog 7b and the bicyclic [1,2,4]triazolo[3,4-a]pyridine derivative 12b.

  DOI：

  10.1007/s00044-010-9469-0
• 作为产物：
  描述：

  2-乙酰基噻吩 在 ammonium acetate 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 14.0h， 生成 4-(4-methoxyphenyl)-2-oxo-6-(thiophen-2-yl)-1,2-dihydropyridine-3-carbonitrile
  参考文献：
  名称：

  A facile synthesis of some 3-cyano-1,4,6-trisubstituted-2(1H)-pyridinones and their biological evaluation as anticancer agents

  摘要：

  The synthesis of some new 3-cyano-1,4,6-trisubstituted-2(1H)-pyridinones supported with various pharmacophores and functionalities at positin-1 is described. The in vitro anticancer activity of 24 of the newly synthesized compounds was evaluated according to the protocol of the NCI in vitro disease-oriented human cells screening panel assay. The results revealed that five compounds 4a-c, 7b, and 12b were able to display moderate antitumor potential against some of the tested subpanel tumor cell lines at the GI(50) and TGI levels, however, with marginal or no cytotoxic (LC(50)) activity. The obtained data suggested that better antitumor activity was linked to derivatives with either 4-bromophenyl or 3,4-dimethoxyphenyl moieties, together with a 1-methyl-1H-pyrrol-2-yl counter part at positions 6 and 4, respectively. Consequently, the 3-cyano-4-(1-methyl-1H-pyrrol-2-yl)-6-(4-bromophenyl or 3,4-dimethoxyphenyl)-2(1H)-pyridinones 4a and 4b, could be considered as the most active members identified in this investigation as evidenced from their relative higher growth inhibitory (GI(50) (MG-MID) 77.6 and 67.6 mu M, respectively) and cytostatic (TGI (MG-MID) 85.1 and 95.5 mu M, respectively) activities, when compared with the substituted thiocarbamoyl analog 7b and the bicyclic [1,2,4]triazolo[3,4-a]pyridine derivative 12b.

  DOI：

  10.1007/s00044-010-9469-0

文献信息

• Eco-friendly synthesis of novel cyanopyridine derivatives and their anticancer and PIM-1 kinase inhibitory activities
  作者：Khaled A.M. Abouzid、Ghada H. Al-Ansary、Abeer M. El-Naggar

  DOI：10.1016/j.ejmech.2017.04.024

  日期：2017.7

  compounds showed good to moderate anti-proliferative activity against HepG2 and HCT-116 cell lines while only few compounds showed significant cytotoxic activity against MCF-7 cell line. Further, the Pim-1 kinase inhibitory activity for the two series was evaluated where most of the tested compounds showed marked Pim-1 kinase inhibitory activity (26%-89%). Moreover, determination of the IC50 values

  最近证明靶向Pim-1激酶对于克服癌症扩散是有利可图的。在当前的研究中，我们报告了针对Pim-1激酶的两个新系列的2个新系列的2-氨基氰基吡啶系列（5a-g）和2-氧代氰基吡啶系列（6a-g）的设计，合成和生物学评估。评价所有新合成的化合物对三种细胞系的体外抗癌活性，这三种细胞系分别是肝癌细胞系（HepG2），结肠癌细胞系（HCT-116）和乳腺癌细胞系（ MCF-7）。大多数化合物对HepG2和HCT-116细胞系表现出良好至中度的抗增殖活性，而只有少数化合物对MCF-7细胞系表现出明显的细胞毒活性。进一步，评估了这两个系列的Pim-1激酶抑制活性，其中大多数受试化合物均显示出显着的Pim-1激酶抑制活性（26％-89％）。此外，IC50值的测定揭示了亚微摩尔范围内非常有效的分子，其中化合物6c的IC50值为0.94μM。而且，对最有效的化合物6c进行了凋亡研究，以评估我们化合物的促凋亡
• 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.
• UV protective textile: Experimental and DFT computational studies on the function of some metal complexes of hydrazide derivatives on cellulose fabrics
  作者：Saeed El‐Sayed Saeed、Meaad Aldubayyan、Ahmed N. Al‐Hakimi、Wael A. El‐Sayed、Jawza Sh Alnawmasi、Marwa M. Abd El‐Hady、M. S. A. Abdel‐Mottaleb

  DOI：10.1002/aoc.7140

  日期：2023.8

  and pyridine derivatives to prepare new textile-protective agents with improved UV protection factor (UPF) factor. This embodies the preparation and characterization of “2-((3-cyano-4-(4-methoxyphenyl)-6-(thiophene-2-yl)pyridine-2-yl)oxy)acetohydrazide” (HZ) in complex with Ni(II), Cu(II), Zn(II), or Cd(II), using proton nuclear magnetic resonance (1H NMR), carbon-13 nuclear magnetic resonance (13C

  紫外线 (UV) 辐射对皮肤有害。因此，利用噻吩和吡啶衍生物的特性，制备了具有改进的紫外线防护因子（UPF）的新型纺织品防护剂。这体现了使用质子核磁共振（ 1 H NMR）、碳 13核磁共振（13C NMR）、X 射线衍射分析（XRD）、傅里叶变换红外光谱（FTIR）和热分析技术。使用 FTIR 光谱、X 射线光谱和扫描电子显微镜-能量色散 X 射线分析 (SEM-EDX) 对棉织物基纤维素 (CELL) 与合成试剂的复合物进行表征，揭示了酰肼及其金属复合物的沉积在纤维素纤维上。有趣的是，观察到纤维素与 Cu(II) 的络合具有最高的 UPF 值。使用密度泛函理论 (DFT) 计算反应性指数支持了这一发现，其中发现改性织物的亲电性参数与 UPF 相关，其中 Cu(II) 显示最高值。因此，合成的复合物可以，
• GHONEIM, K. M.;BADRAN, M. M.;SHAABAN, M. A.;EL-MELIGIE, S., EGYPT. J. PHARM. SCI., 29,(1988) N 1-4, C. 553-561
  作者：GHONEIM, K. M.、BADRAN, M. M.、SHAABAN, M. A.、EL-MELIGIE, S.

  DOI：——

  日期：——
• A facile synthesis of some 3-cyano-1,4,6-trisubstituted-2(1H)-pyridinones and their biological evaluation as anticancer agents
  作者：Sherif A. F. Rostom、Hassan M. Faidallah、Mohammed S. Al-Saadi

  DOI：10.1007/s00044-010-9469-0

  日期：2011.11

  The synthesis of some new 3-cyano-1,4,6-trisubstituted-2(1H)-pyridinones supported with various pharmacophores and functionalities at positin-1 is described. The in vitro anticancer activity of 24 of the newly synthesized compounds was evaluated according to the protocol of the NCI in vitro disease-oriented human cells screening panel assay. The results revealed that five compounds 4a-c, 7b, and 12b were able to display moderate antitumor potential against some of the tested subpanel tumor cell lines at the GI(50) and TGI levels, however, with marginal or no cytotoxic (LC(50)) activity. The obtained data suggested that better antitumor activity was linked to derivatives with either 4-bromophenyl or 3,4-dimethoxyphenyl moieties, together with a 1-methyl-1H-pyrrol-2-yl counter part at positions 6 and 4, respectively. Consequently, the 3-cyano-4-(1-methyl-1H-pyrrol-2-yl)-6-(4-bromophenyl or 3,4-dimethoxyphenyl)-2(1H)-pyridinones 4a and 4b, could be considered as the most active members identified in this investigation as evidenced from their relative higher growth inhibitory (GI(50) (MG-MID) 77.6 and 67.6 mu M, respectively) and cytostatic (TGI (MG-MID) 85.1 and 95.5 mu M, respectively) activities, when compared with the substituted thiocarbamoyl analog 7b and the bicyclic [1,2,4]triazolo[3,4-a]pyridine derivative 12b.