ethyl 2-(p-tolyl)quinoline-4-carboxylate | 80221-41-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: ethyl 2-(p-tolyl)quinoline-4-carboxylate
• 英文别名: Ethyl 2-(4-methylphenyl)-quinoline-4-carboxylate；ethyl 2-(4-methylphenyl)quinoline-4-carboxylate
• CAS: 80221-41-6
• 化学式: C₁₉H₁₇NO₂
• 分子量: 291.349
• InChiKey: MLKSFYIQZRFIIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-(p-tolyl)quinoline-4-carboxylate 在 盐酸 、 一水合肼 、 sodium nitrite 作用下， 反应 2.0h， 生成 2-p-tolyl-quinoline-4-carbonyl azide
  参考文献：
  名称：

  John, Journal fur praktische Chemie (Leipzig 1954), 1931, vol. <2> 131, p. 314,318

  摘要：

  DOI：
• 作为产物：
  描述：

  2-对甲苯基喹啉-4-羧酸 在 乙醇 、 硫酸 作用下， 生成 ethyl 2-(p-tolyl)quinoline-4-carboxylate
  参考文献：
  名称：

  John, Journal fur praktische Chemie (Leipzig 1954), 1931, vol. <2> 131, p. 314,318

  摘要：

  DOI：

文献信息

• Pharmaceutical compositions containing naphthalene-and
  申请人：Rhone-Poulenc Sante

  公开号：US04684652A1

  公开（公告）日：1987-08-04

  Compounds of the formula: ##STR1## in which R.sub.1 is C.sub.1-6 alkyl, phenyl, C.sub.3-6 cycloalkyl, phenylalkyl, cycloalkyl-alkyl or ##STR2## R.sub.3 and R.sub.4 being H or alkyl, R.sub.5 being alkenyl or alkynyl, and the sum of the carbon atoms in R.sub.3, R.sub.4 and R.sub.5 being 2 to 5, R.sub.2 is as defined for R.sub.1 and may also represent ##STR3## in which n is 0, 1, 2 or 3, it also being possible for R.sub.1 and R.sub.2 to form, with the nitrogen atom to which they are attached, a 5-, 6- or 7-membered heterocyclic radical which can contain another hetero-atom chosen from O and N and which can carry 1 or 2 substituents, Z is phenyl, pyridinyl, thienyl, thiazol-2-yl or substituted phenyl, X and R.sub.0 are H, halogen, C.sub.1-3 alkyl, C.sub.1-3 alkoxy, nitro or CF.sub.3, A represents N or CH and E represents N or CH, some of which are known compounds, are therapeutically useful compounds useful in the treatment of anxiety states or of pulmonary, renal, circulatory or cardiovascular disorders.

  公式中的化合物：##STR1## 其中R.sub.1是C.sub.1-6烷基，苯基，C.sub.3-6环烷基，苯基烷基，环烷基-烷基或##STR2## R.sub.3和R.sub.4为H或烷基，R.sub.5为烯基或炔基，且R.sub.3，R.sub.4和R.sub.5中碳原子的总和为2至5，R.sub.2的定义与R.sub.1相同，也可以表示为##STR3## 其中n为0、1、2或3，R.sub.1和R.sub.2也可以与它们所连接的氮原子形成一个5-、6-或7-成员的杂环基团，该杂环基团可以含有另一个来自O和N的杂原子，并且可以携带1个或2个取代基，Z是苯基，吡啶基，噻吩基，噻唑-2-基或取代的苯基，X和R.sub.0是H，卤素，C.sub.1-3烷基，C.sub.1-3烷氧基，硝基或CF.sub.3，A代表N或CH，E代表N或CH，其中一些是已知的化合物，是有治疗焦虑状态或肺、肾、循环或心血管障碍的药用化合物。
• New quinoline/chalcone hybrids as anti-cancer agents: Design, synthesis, and evaluations of cytotoxicity and PI3K inhibitory activity
  作者：Samar H. Abbas、Amer Ali Abd El-Hafeez、Mai E. Shoman、Monica M. Montano、Heba A. Hassan

  DOI：10.1016/j.bioorg.2018.10.064

  日期：2019.2

  A series of quinoline-chalcone hybrids was designed as potential anti-cancer agents, synthesized and evaluated. Different cytotoxic assays revealed that compounds experienced promising activity. Compounds 9i and 9j were the most potent against all the cell lines tested with IC50 = 1.91-5.29 µM against A549 and K-562 cells. Mechanistically, 9i and 9j induced G2/M cell cycle arrest and apoptosis in both

  设计了一系列喹啉-查耳酮杂化物作为潜在的抗癌药，进行了合成和评估。不同的细胞毒性试验表明，化合物具有良好的活性。化合物9i和9j对所有测试的A549和K-562细胞的IC50 = 1.91-5.29 µM的细胞系最有效。从机理上讲，9i和9j诱导了A549和K562细胞的G2 / M细胞周期停滞和凋亡。此外，当针对两种提及的化合物进行测试时，所有PI3K亚型均被非选择性抑制，IC50为52-473 nM，其中9i对PI3K-γ最有效（IC50 = 52 nM）。9i和9j的对接显示可能在PI3K-γ同工型的活性位点与基本缬氨酸残基形成H键。同时，Western印迹分析显示9i和9j抑制了PI3K，Akt，mTOR，以及A549和K562细胞中的GSK-3β，提示阻断PI3K / Akt / mTOR途径与上述抗肿瘤活性相关。总之，我们的发现通过抑制PI3K / Akt / mTOR途径，支
• Ethyl lactate-involved three-component dehydrogenative reactions: biomass feedstock in diversity-oriented quinoline synthesis
  作者：Lu Yang、Jie-Ping Wan

  DOI：10.1039/d0gc00738b

  日期：——

  Three-component reactions of ethyl/methyl lactate, anilines and aldehydes providing quinolines have been developed via simple iron(III) chloride catalysis without using an additional organic medium or external oxidant. This three-component protocol shows high efficiency and broad substrate tolerance, allowing quick access to diverse quinoline products under neat reaction conditions. The results reported

  通过简单的氯化铁（III）催化反应，无需使用额外的有机介质或外部氧化剂，即可开发出乙基/乳酸甲酯，苯胺和醛提供喹啉的三组分反应。该三组分方案显示出高效率和广泛的底物耐受性，可以在纯净的反应条件下快速获得各种喹啉产物。本文报道的结果揭示了绿色生物质原料在有价值的有机产物的清洁合成中的重要新应用。
• Pharmaceutical compositions containing azanaphthalene-carboxamide
  申请人：Rhone-Poulenc Sante

  公开号：US04711890A1

  公开（公告）日：1987-12-08

  Compounds of the formula: ##STR1## in which R.sub.1 is C.sub.1-6 alkyl, phenyl, C.sub.3-6 cycloalkyl, phenylalkyl, cycloalkyl-alkyl or ##STR2## R.sub.3 and R.sub.4 being H or alkyl, R.sub.5 being alkenyl or alkynyl, and the sum of the carbon atoms in R.sub.3, R.sub.4 and R.sub.5 being 2 to 5, R.sub.2 is as defined for R.sub.1 and may also represent ##STR3## in which n is 0, 1, 2 or 3, it also being possible for R.sub.1 and R.sub.2 to form, with the nitrogen atom to which they are attached, a 5-, 6- or 7-membered heterocyclic radical which can contain another hetero-atom chosen from O and N and which can carry 1 or 2 substituents, Z is phenyl, pyridinyl, thienyl, thiazol-2-yl or substituted phenyl, X and R.sub.0 are H, halogen, C.sub.1-3 alkyl, C.sub.1-3 alkoxy, nitro or CF.sub.3, A represents N or CH and E represents N or CH, some of which are known compounds, are therapeutically useful compounds useful in the treatment of anxiety states or of pulmonary, renal, circulatory or cardiovascular disorders.

  这个化合物的式子为：##STR1## 其中R.sub.1是C.sub.1-6烷基，苯基，C.sub.3-6环烷基，苯基烷基，环烷基-烷基或##STR2## R.sub.3和R.sub.4为H或烷基，R.sub.5为烯基或炔基，且R.sub.3，R.sub.4和R.sub.5中的碳原子总数为2到5，R.sub.2与R.sub.1的定义相同，也可以表示为##STR3## 其中n为0，1，2或3，R.sub.1和R.sub.2也可以与它们附着的氮原子形成一个5、6或7成员的杂环基团，该杂环基团可以含有另一个从O和N中选择的杂原子，并且可以携带1或2个取代基，Z为苯基，吡啶基，噻吩基，噻唑-2-基或取代苯基，X和R.sub.0为H，卤素，C.sub.1-3烷基，C.sub.1-3烷氧基，硝基或CF.sub.3，A代表N或CH，E代表N或CH，其中一些已知化合物，在治疗焦虑症或肺部，肾脏，循环或心血管疾病方面有用。
• Metal-free three-component assemblies of anilines, α-keto acids and alkyl lactates for quinoline synthesis and their anti-inflammatory activity
  作者：Lizhu Huang、Lu Yang、Jie-Ping Wan、Liyun Zhou、Yunyun Liu、Guifeng Hao

  DOI：10.1039/d2ob00661h

  日期：——

  A new and metal-free three-component method for the synthesis of 2,4-disubstituted quinolines via the reactions of anilines, α-keto acids and alkyl lactates is reported. The reactions proceed in the presence of p-toluene sulfonic acid (p-TSA) and tert-butyl peroxybenzoate (TBPB) to provide diverse quinoline products via the construction of new CC double, C–C single and CN double bonds without producing

  报道了一种通过苯胺、α-酮酸和乳酸烷基酯反应合成 2,4-二取代喹啉的新型无金属三组分方法。该反应在对甲苯磺酸 ( p -TSA) 和过氧苯甲酸叔丁酯 (TBPB)的存在下进行，通过构建新的 C C 双键、C-C 单键和 C N 双键来提供多种喹啉产物，而不会产生任何基于质量的有机副产品。值得注意的是，喹啉的抗炎活性已通过测量其抑制脂多糖 (LPS) 诱导的 RAW264.7 细胞释放 NO 的能力来研究，从而鉴定出4i，4t和4x作为体外有效的抗炎化合物。