7-chloro-4-(2-(4-fluorobenzylidene)hydrazinyl)quinoline | 71429-16-8

• 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: 7-chloro-4-(2-(4-fluorobenzylidene)hydrazinyl)quinoline
• 英文别名: 7-chloro-N-[(4-fluorophenyl)methylideneamino]quinolin-4-amine
• CAS: 71429-16-8
• 化学式: C₁₆H₁₁ClFN₃
• 分子量: 299.735
• InChiKey: LGXWVNVCPIIGPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-chloro-4-(2-(4-fluorobenzylidene)hydrazinyl)quinoline 、 氯乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以75%的产率得到3-chloro-1-((7-chloroquinolin-4-yl)amino)-4-(4-fluorophenyl)azetidin-2-one
  参考文献：
  名称：

  Quinoline-azetidinone hybrids: Synthesis and in vitro antiproliferation activity against Hep G2 and Hep 3B human cell lines

  摘要：

  In search of new heterocyclic anticancer agents, a new quinoline-azetidinone hybrid template have been designed, synthesized and screened for their cytotoxic activity against human cancer cell lines such as Hep G2, and Hep 3B by the MTT assay and results were compared with paclitaxel, 5-fluorouracil and doxorubicin. Interestingly, some of the compounds were found significantly active against both cell lines. The compound 6f (IC50 = 0.04 +/- 0.01 mu M) exhibited potent antiproliferation activity against Hep G2 cell line, and 6j compound (IC50 = 0.66 +/- 0.01 mu M) demonstrated potent antiproliferation activity against Hep 3B cell line and provide to be more potent as cytotoxic agents than standard drugs. Morphological changes suggest the induction of apoptosis and describe the mechanism of action of these hybrid antitumor agents. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.02.043
• 作为产物：
  描述：

  4,7-二氯喹啉 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 32.0h， 生成 7-chloro-4-(2-(4-fluorobenzylidene)hydrazinyl)quinoline
  参考文献：
  名称：

  Quinoline-azetidinone hybrids: Synthesis and in vitro antiproliferation activity against Hep G2 and Hep 3B human cell lines

  摘要：

  In search of new heterocyclic anticancer agents, a new quinoline-azetidinone hybrid template have been designed, synthesized and screened for their cytotoxic activity against human cancer cell lines such as Hep G2, and Hep 3B by the MTT assay and results were compared with paclitaxel, 5-fluorouracil and doxorubicin. Interestingly, some of the compounds were found significantly active against both cell lines. The compound 6f (IC50 = 0.04 +/- 0.01 mu M) exhibited potent antiproliferation activity against Hep G2 cell line, and 6j compound (IC50 = 0.66 +/- 0.01 mu M) demonstrated potent antiproliferation activity against Hep 3B cell line and provide to be more potent as cytotoxic agents than standard drugs. Morphological changes suggest the induction of apoptosis and describe the mechanism of action of these hybrid antitumor agents. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.02.043

文献信息

• Synthesis and Evaluation of Anti-Tuberculosis and Anti-Cancer Activities of Hydrazones and N-Acylhydrazones by Using Sonochemistry, A New General Procedure
  作者：Ligia Souza da Silveira Pinto、Marcus V. N. de Souza、Carlos R. Kaiser

  DOI：10.2174/1570180814666161121120414

  日期：2017.6.6

  report a new general and efficient synthesis of these classes with different aromatic and heteroaromatic nucleus assisted by ultrasound and their respective anti-tuberculosis and anti-cancer activities. Method: Derivatives 7-chloroquinoline 10 and 12 were the most promising compounds against cancer and TB, respectively. Conclusion: Unfortunately all new hydrazones and N-acylhydrazones evaluated displayed

  背景：在继续进行声化学研究的过程中，由于和N-酰基hydr在药物开发中的重要性和应用，在这项工作中，我们报告了一种新的通用且有效的合成方法，这些方法通过超声和​​超声辅助，合成了具有不同芳族和杂芳族核的这些类别。它们各自的抗结核和抗癌活性。 方法：衍生物7-氯喹啉10和12分别是最有前途的抗癌和抗结核药物。 结论：不幸的是，所有评估的新new和N-酰基hydr均未显示出抗癌和抗结核活性。
• Synthesis and antitubercular activity of 7-chloro-4-quinolinylhydrazones derivatives
  作者：André L.P. Candéa、Marcelle de L. Ferreira、Karla C. Pais、Laura N.de F. Cardoso、Carlos R. Kaiser、Maria das Graças M.de O. Henriques、Maria C.S. Lourenço、Flávio A.F.M. Bezerra、Marcus V.N. de Souza

  DOI：10.1016/j.bmcl.2009.09.098

  日期：2009.11

  A series of twenty-one 7-chloro-4-quinolinylhydrazones (3a-u) have been synthesized and evaluated for their in vitro antibacterial activity against Mycobacterium tuberculosis H(37)Rv. The compounds 3f, 3i and 3o were non-cytotoxic and exhibited an important minimum inhibitory concentration (MIC) activity (2.5 mu g/mL), which can be compared with that of the first line drugs, ethambutol (3.12 mu g/mL) and rifampicin (2.0 mu g/mL). These results can be considered an important start point for the rational design of new leads for anti-TB compounds. (C) 2009 Elsevier Ltd. All rights reserved.