4-甲基-2-氧代-6-苯基-1H-吡啶-3-腈 | 4240-97-5

• 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
• 中文名称: 4-甲基-2-氧代-6-苯基-1H-吡啶-3-腈
• 英文名称: 4-methyl-2-oxo-6-phenyl-1,2-dihydropyridine-3-carbonitrile
• 英文别名: 4-methyl-2-oxo-6-phenyl-1H-pyridine-3-carbonitrile
• CAS: 4240-97-5
• 化学式: C₁₃H₁₀N₂O
• 分子量: 210.235
• InChiKey: DIKYSAWZOUGXTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  4-甲基-2-氧代-6-苯基-1H-吡啶-3-腈 在 硫酸 作用下， 反应 4.0h， 以70%的产率得到4-methyl-2-oxo-6-phenyl-1,2-dihydropyridine-3-carboxamide
  参考文献：
  名称：

  3-氨基-4-芳基吡啶-2-2（1Н）-ones的合成及光物理性质

  摘要：

  基于2-氧-1,2-二氢吡啶-3-羧酰胺的霍夫曼反应，已经开发了一种制备恶唑-[5,4 - b ]吡啶-2-2 （1 H）-的方法。恶唑并[5,4 - b ]吡啶-2（1 H）-one的水解和2-氧-1,2-二氢吡啶-3-羧酰胺的霍夫曼反应产生3-氨基吡啶-2（1 H）-one，包括该系列中的4-芳基取代衍生物，其有效荧光粉的量子产率高达0.78。通过紫外和发光光谱法研究了3-氨基吡啶-2（1 H）-1的光物理性质，揭示了其结构与光物理性质之间的关系。

  DOI：

  10.1055/s-0039-1690231
• 作为产物：
  描述：

  苯乙酮 在 三乙烯二胺 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 生成 4-甲基-2-氧代-6-苯基-1H-吡啶-3-腈
  参考文献：
  名称：

  Discovery and structure–activity relationships study of novel thieno[2,3-b]pyridine analogues as hepatitis C virus inhibitors

  摘要：

  Current treatment for hepatitis C is barely satisfactory, there is an urgent need to develop novel agents for combating hepatitis C virus infection. This study discovered a new class of thieno[ 2,3-b] pyridine derivatives as HCV inhibitors. First, a hit compound characterized by a thienopyridine core was identified in a cell-based screening of our privileged small molecule library. And then, structure activity relationship study of the hit compound led to the discovery of several potent compounds without obvious cytotoxicity in vitro (12c, EC50 = 3.3 mu M, SI > 30.3, 12b, EC50 = 3.5 mu M, SI > 28.6, 10l, EC50 = 3.9 mu M, SI > 25.6, 12o, EC50 = 4.5 mu M, SI > 22.2, respectively). Although the mechanism of them had not been clearly elucidated, our preliminary optimization of this class of compounds had provided us a start point to develop new anti-HCV agents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.075

文献信息

• Discovery of quinolone derivatives as antimycobacterial agents
  作者：Kun-Lin Liu、Fei Teng、Lu Xiong、Xiao Li、Chao Gao、Luo-Ting Yu

  DOI：10.1039/d0ra09250a

  日期：——

  6b21: MIC against M. tb H₃₇Rv = 1.2 μg mL⁻¹, MIC against drug-resistant strains = 0.9 μg mL⁻¹, solubility = 132 μg mL⁻¹, non-cytotoxicity.

  6b21：对H37Rv结核分枝杆菌的最小抑菌浓度为1.2 μg/mL，对耐药菌株的最小抑菌浓度为0.9 μg/mL，溶解度为132 μg/mL，无细胞毒性。
• [EN] NOVEL PYRIDINE DERIVATIVES, A PROCESS FOR THEIR PREPARATION AND A PHARMACEUTICAL COMPOSITION CONTAINING THE SAME<br/>[FR] NOUVEAUX DERIVES DE PYRIDINE, LEUR PROCEDE DE PREPARATION ET COMPOSITION PHARMACEUTIQUE EN CONTENANT
  申请人：SK CHEMICALS CO LTD

  公开号：WO2005063768A1

  公开（公告）日：2005-07-14

  This invention relates to novel pyridine derivatives having an inhibitory effect on production of cytokines, which are involved in inflammatory responses, thus suggesting its usefulness as therapeutic agents for treating diseases related to inflammation, immune, chronic inflammation as well as an agent having an anti-inflammatory and analgesic effect. Further, this invention relates to a method of manufacturing the same and a pharmaceutical composition containing the same.

  这项发明涉及具有抑制细胞因子产生作用的新型吡啶衍生物，这些细胞因子参与炎症反应，因此表明其可用作治疗与炎症、免疫、慢性炎症相关疾病的治疗剂，同时具有抗炎和镇痛作用的药剂。此外，这项发明涉及制造该化合物的方法和含有该化合物的药物组合物。
• Green Synthetic Approach and Antimicrobial Evaluation for Some Novel Pyridyl Benzoate Derivatives
  作者：H. A. Eldeab

  DOI：10.1134/s1070428019070200

  日期：2019.7

  4-chlorobenzoates have been synthesized by microwave-assisted condensation of the corresponding 2-oxo-1,2-dihydropyridine-3-carbonitriles with 4-chlorobenzoyl chloride under solvent-free conditions. Alternatively, some compounds have also been prepared by conventional heating in methylene chloride in the presence of triethylamine. The structure of the synthesized compounds has been confirmed by spectral data (FTIR

  在无溶剂的条件下，通过微波辅助缩合相应的2-oxo-1,2-二氢吡啶-3-腈与4-氯苯甲酰氯，合成了两个系列的4-氯苯甲酸吡啶基酯。或者，还通过在三乙胺存在下在二氯甲烷中常规加热来制备一些化合物。合成化合物的结构已通过光谱数据（FTIR，1D和2D NMR）证实。评价了新的苯甲酸吡啶基酯对革兰氏阴性和革兰氏阳性细菌的抗菌活性。3-氰基-5-[（4-羟基苯基）二氮烯基] -4-甲基-6-苯基吡啶-2-基4-氯苯甲酸酯对革兰氏阳性细菌（枯草芽孢杆菌和金黄色葡萄球菌）的活性）与用作标准抗生素的丁胺卡那霉素相当。
• Structure–Activity Relationship Studies for Enhancer of Zeste Homologue 2 (EZH2) and Enhancer of Zeste Homologue 1 (EZH1) Inhibitors
  作者：Xiaobao Yang、Fengling Li、Kyle D. Konze、Jamel Meslamani、Anqi Ma、Peter J. Brown、Ming-Ming Zhou、Cheryl H. Arrowsmith、H. Ümit Kaniskan、Masoud Vedadi、Jian Jin

  DOI：10.1021/acs.jmedchem.6b00855

  日期：2016.8.25

  EZH2 or EZH1 (enhancer of zeste homologue 2 or 1) is the catalytic subunit of polycomb repressive complex 2 (PRC2) that catalyzes methylation of histone H3 lysine 27 (H3K27). PRC2 hyperactivity and/or hypertrimethylation of H3K27 are associated with numerous human cancers, therefore inhibition of PRC2 complex has emerged as a promising therapeutic approach. Recent studies have shown that EZH2 and EZH1

  EZH2或EZH1（zeste同源物2或1的增强剂）是多梳抑制复合物2（PRC2）的催化亚基，可催化组蛋白H3赖氨酸27（H3K27）的甲基化。PRC2的过度活跃和/或H3K27的过度三甲基化与许多人类癌症相关，因此抑制PRC2的复合体已成为一种有前途的治疗方法。最近的研究表明，EZH2和EZH1在功能上不是多余的，抑制EZH2和EZH1两者对于阻止某些癌症（如混合谱系白血病（MLL）重排的白血病）的进展是必要的。尽管EZH2抑制剂的发现取得了重大进展，但尚未进行系统的结构-活性关系（SAR）研究来研究EZH2和EZH1抑制剂之间的选择性。这里，5）研究结构变化对EZH2和EZH1抑制和选择性的影响。
• An Eco-Friendly Technique: Solvent-Free Microwave Synthesis and Docking Studies of Some New Pyridine Nucleosides and Their Pharmacological Significance
  作者：Majed Alrobaian、Sana Al Azwari、Amany Belal、Hany A. Eldeab

  DOI：10.3390/molecules24101969

  日期：——

  4″,6″-tetra-O-acetyl-β-d-galacto pyranosyloxy) pyridines and 3-cyano-2-(2″,3″,4″,6″-tetra-O-acetyl-β-d-galactopyranosyloxy) pyridines were synthesized in high yields utilizing a microwave-assisted synthesis tool guided by the principles of green chemistry. The chemical structures of the new substances were confirmed on the basis of their elemental analysis and spectroscopic data (FT-IR, 1D, 2D-NMR).

  两个系列的新型5-芳基-3-氰基-2-(2″,3″,4″,6″-四-O-乙酰基-β-d-吡喃半乳糖氧基)吡啶和3-氰基-2-(2 ″,3″,4″,6″-四-O-乙酰基-β-d-吡喃半乳糖氧基)吡啶是利用以绿色化学原理为指导的微波辅助合成工具以高产率合成的。根据元素分析和光谱数据（FT-IR、1D、2D-NMR）确认了新物质的化学结构。研究了针对不同细菌菌株的活性。还讨论了新化合物的抗癌潜力。在这项研究工作中，分子对接被用作工具，以更好地了解潜在化疗靶标 (DHFR) 的最有希望的衍生物的可能相互作用、亲和力和预期结合模式。