7-chloro-4-(2-(4-nitrobenzylidene)hydrazineyl)quinoline | 391616-98-1

• 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-nitrobenzylidene)hydrazineyl)quinoline
• 英文别名: 7-chloro-4-(2-(4-nitrobenzylidene)hydrazinyl)quinoline；7-chloro-N-[(4-nitrophenyl)methylideneamino]quinolin-4-amine
• CAS: 391616-98-1
• 化学式: C₁₆H₁₁ClN₄O₂
• 分子量: 326.742
• InChiKey: HTAIILREQVWDQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 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：
  83.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-chloro-4-(2-(4-nitrobenzylidene)hydrazineyl)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40%的产率得到3-chloro-1-((7-chloroquinolin-4-yl)amino)-4-(4-nitrophenyl)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 12.0h， 生成 7-chloro-4-(2-(4-nitrobenzylidene)hydrazineyl)quinoline
  参考文献：
  名称：

  芳基喹啉基衍生物作为抗炎剂，可抑制巨噬细胞中的TLR4活化。

  摘要：

  在简单的反应条件下，合成了一系列芳基7-氯喹啉基7衍生物（3a-u），产率为55-76％。基于它们在用脂多糖（LPS）刺激后抑制巨噬细胞促炎细胞因子分泌的能力，评估了它们的抗炎活性。三种化合物似乎是有希望的抗炎药。使用一系列的生化，分子和显微技术，进一步研究了强效化合物3e的炎症活性机制。进行了进一步的结构活性关系（SAR）研究，以验证活性化合物的抗炎活性。我们的实验数据表明，活性部分即

  DOI：

  10.1016/j.ejps.2019.04.016

文献信息

• Design, Synthesis, Antimalarial Activity and Docking Study of 7-Chloro-4- (2-(substituted benzylidene)hydrazineyl)quinolines
  作者：Jahnabi Kalita、Dipak Chetia、Mithun Rudrapal

  DOI：10.2174/1573406415666190806154722

  日期：2020.11.6

  antimalarial drug agents is therefore an urgent requirement to fight against resistant malaria. Objective: The objective of this work was to develop novel quinoline-baed antimalarial agents that would be active against resistant P. falciparum malaria. Methods: Some 7-chloro-4-(2-(substituted benzylidene)hydrazineyl)quinolines were synthesized for the evaluation of their potential as possible antimalarial

  背景：由于恶性疟原虫耐药菌株的出现，疟疾是一种日益严重的传染病负担。由于可用的抗疟药的治疗功效有限，因此开发有效的抗疟药是对抗耐药性疟疾的迫切需求。 目的：这项工作的目的是开发新的喹啉类抗疟药，它们对耐药性恶性疟原虫疟疾具有活性。 方法：合成了一些7-氯-4-（2-（取代的亚苄基）肼基）喹啉，以评估其作为可能的抗疟药，特别是抗疟疾的潜力。在体外评估了合成化合物对恶性疟原虫血液阶段寄生虫的抗疟活性。此外，还使用计算机模拟工具进行了分子对接和类似药物的研究，包括ADMET（吸收，分布，代谢，消除和毒性）研究。 结果：结果揭示了合成的7-氯-4-（2-（取代的亚苄基）肼基）喹啉类药物对恶性疟原虫的体外抗疟活性。对接研究调查了合成喹啉作为新型纤溶酶2抑制剂的抗疟疾功效。药物相似性预测显示出可接受的药物相似性和ADMET属性。 结论：根据我们的发现，可以得出结论，7-氯-4-（2-（取代的亚苄基）肼
• 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.
• Aryl quinolinyl hydrazone derivatives as anti-inflammatory agents that inhibit TLR4 activation in the macrophages
  作者：Utsab Debnath、Suprabhat Mukherjee、Nikhilesh Joardar、Santi P. Sinha Babu、Kuladip Jana、Anup Kumar Misra

  DOI：10.1016/j.ejps.2019.04.016

  日期：2019.6

  mechanism of inflammatory activity of the potent compound 3e was further investigated using a series of biochemical, molecular and microscopic techniques. Further structure activity relationship (SAR) study was carried out to validate the anti-inflammatory activities of the active compounds. Our experimental data revealed that the active moiety i.e. compound 3e majorly causes inhibition of TLR4 signaling

  在简单的反应条件下，合成了一系列芳基7-氯喹啉基7衍生物（3a-u），产率为55-76％。基于它们在用脂多糖（LPS）刺激后抑制巨噬细胞促炎细胞因子分泌的能力，评估了它们的抗炎活性。三种化合物似乎是有希望的抗炎药。使用一系列的生化，分子和显微技术，进一步研究了强效化合物3e的炎症活性机制。进行了进一步的结构活性关系（SAR）研究，以验证活性化合物的抗炎活性。我们的实验数据表明，活性部分即
• Quinoline-azetidinone hybrids: Synthesis and in vitro antiproliferation activity against Hep G2 and Hep 3B human cell lines
  作者：S.G. Alegaon、P. Parchure、L.D. Araujo、P.S. Salve、K.R. Alagawadi、S.S. Jalalpure、V.M. Kumbar

  DOI：10.1016/j.bmcl.2017.02.043

  日期：2017.4

  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.