2-(4-methylphenyl)quinoline-4-carbohydrazide | 350988-64-6

• 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: 2-(4-methylphenyl)quinoline-4-carbohydrazide
• 英文别名: 2-p-tolyl-quinoline-4-carboxylic acid hydrazide；2-p-Tolyl-chinolin-4-carbonsaeure-hydrazid
• CAS: 350988-64-6
• 化学式: C₁₇H₁₅N₃O
• mdl: MFCD01447251
• 分子量: 277.326
• InChiKey: TZQWANBRSTUSOU-UHFFFAOYSA-N

物化性质

• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.058
• 拓扑面积：
  68
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  2-(4-methylphenyl)quinoline-4-carbohydrazide 在 盐酸 、 sodium nitrite 作用下， 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：

  ethyl 2-(p-tolyl)quinoline-4-carboxylate 在 一水合肼 作用下， 以 乙醇 为溶剂， 以90%的产率得到2-(4-methylphenyl)quinoline-4-carbohydrazide
  参考文献：
  名称：

  新型喹啉/查尔酮杂化物作为抗癌剂：细胞毒性和PI3K抑制活性的设计，合成和评估。

  摘要：

  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

  DOI：

  10.1016/j.bioorg.2018.10.064

文献信息

• 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
• Musante; Parrini, Gazzetta Chimica Italiana, 1954, vol. 84, p. 209,220
  作者：Musante、Parrini

  DOI：——

  日期：——
• Hydrazones of 2-aryl-quinoline-4-carboxylic acid hydrazides: Synthesis and preliminary evaluation as antimicrobial agents
  作者：Kamel A. Metwally、Lobna M. Abdel-Aziz、El-Sayed M. Lashine、Mohamed I. Husseiny、Rania H. Badawy

  DOI：10.1016/j.bmc.2006.08.022

  日期：2006.12

  A new series of 2-arylquinoline-4-carboxylic acid hydrazide-hydrazones was synthesized using an appropriate synthetic route. All the target compounds were evaluated for their in vitro antimicrobial activity against Staphylococcus aureus as an example for Gram-positive bacteria, Escherichia coli as an example for Gram-negative bacteria, and Candida albicans as a representative of fungi. The minimum inhibitory concentration (MIC) was determined for test compounds as well as for reference standards. Among the compounds tested, compounds having nitro substituents at the arylidene moiety showed the most potent antifungal as well as antibacterial activities against E coli. Compound 23 displayed an antifungal activity comparable to that of nystatin. However, none of the compounds demonstrated any antibacterial activity against S. aureus. Hydrophobicity of the target compounds correlated weakly with their antibacterial and antifungal activities. The most potent compounds namely, 7, 18, 19, 22, and 23 were assessed for hemolytic toxicity and found to be non-hemolytic up to a concentration of 100 mu g/mL. In addition, the most potent compound (23) was evaluated for in vitro cytotoxic activity against various cancer cell lines. This compound was found to display no cytotoxic activity but rather it induces the proliferation rate of Hep-G2 cells. (c) 2006 Elsevier Ltd. All rights reserved.
• John, Journal fur praktische Chemie (Leipzig 1954), 1931, vol. <2> 131, p. 314,318
  作者：John

  DOI：——

  日期：——
• Design, synthesis, and biological investigation of quinoline/ciprofloxacin hybrids as antimicrobial and anti-proliferative agents
  作者：Hend A. A. Ezelarab、Heba A. Hassan、Gamal El-Din A. Abuo-Rahma、Samar H. Abbas

  DOI：10.1007/s13738-022-02704-7

  日期：2023.3

  linked quinoline derivatives 6a–c and 8a–c were synthesized and investigated for their antibacterial, antifungal, and anti-proliferative activities. Ciprofloxacin-quinoline-4-yl-1,3,4 oxadiazoles 6a and 6b showed promising anticancer activity against SR- leukemia and UO-31 renal cancer cell lines. The hybrids 8a–c and compound 6b exhibited noticeable antifungal activities against C. Albicans; 8a experienced

  合成了环丙沙星-哌嗪 C-7 连接的喹啉衍生物6a-c和8a-c，并研究了它们的抗菌、抗真菌和抗增殖活性。Ciprofloxacin-quinoline-4-yl-1,3,4 oxadiazoles 6a和6b显示出对 SR- 白血病和 UO-31 肾癌细胞系有希望的抗癌活性。杂交体8a–c和化合物6b对白色念珠菌表现 出显着的抗真菌活性；8a与伊曲康唑相比具有最强的抗真菌活性，MIC 分别为 21.88 µg/mL 和 11.22 µg/mL；分别。大多数衍生物对所有测试菌株都显示出比母体环丙沙星更好的抗菌活性。化合物6b对高度耐药的革兰氏阴性肺炎克雷伯菌最有效，相 对于母体环丙沙星（MIC = 29.51 µg/mL），MIC 为 16.96 µg/mL。K. pneumoniae ( 5EIX ) 和S. aureus gyrase ( 2XCT ) Topo IV 酶活性位点氢化物