7-chloro-4-(3,4-dimethoxy-benzilidenehydrazo)quinoline | 391617-07-5

• 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-(3,4-dimethoxy-benzilidenehydrazo)quinoline
• 英文别名: 7-chloro-N-[(3,4-dimethoxyphenyl)methylideneamino]quinolin-4-amine
• CAS: 391617-07-5
• 化学式: C₁₈H₁₆ClN₃O₂
• 分子量: 341.797
• InChiKey: OFGHMRJNOMPCMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-chloro-4-(3,4-dimethoxy-benzilidenehydrazo)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72%的产率得到3-chloro-1-((7-chloroquinolin-4-yl)amino)-4-(3,4-dimethoxyphenyl)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 2.0h， 生成 7-chloro-4-(3,4-dimethoxy-benzilidenehydrazo)quinoline
  参考文献：
  名称：

  Cytotoxic Activity of Polysubstituted 7-chloro-4-quinolinylhydrazone Derivatives

  摘要：

  我们合成了一系列多取代的 7-氯-4-喹啉腙衍生物（3a-n），并评估了它们对四种癌细胞株的活性。其中，化合物 3a、3c、3h、3i、3j 和 3n 显示出良好的细胞毒性（IC50 范围为 0.7483 至 5.572 μg/mL）。总的来说，我们观察到苯环上甲氧基的存在对该系列化合物的抗癌活性起着重要作用，尤其是当甲氧基位于 3,4 （3h）或 3,4,5 （3j）位时。这些衍生物可被视为合理设计抗肿瘤药物新线索的一个重要发现。

  DOI：

  10.2174/157018012799129837

文献信息

• Cytotoxic Activity of Polysubstituted 7-chloro-4-quinolinylhydrazone Derivatives
  作者：Raquel Carvalho Montenegro、Leticia Veras Lotufo、Manoel Odorico de Moraes、Claudia do O Pessoa、Felipe Augusto Rocha Rodrigues、Marcelle de Lima Ferreira Bispo、Bruna Abreu Freire、Carlos Roland Kaiser、Marcus Vinicius Nora de Souza

  DOI：10.2174/157018012799129837

  日期：2012.3.1

  A series of fourteen polysubstituted 7-chloro-4-quinolinylhydrazone derivatives (3a-n) has been synthesized and evaluated for their activity against four cancer cell lines. Among them, compounds 3a, 3c, 3h, 3i, 3j and 3n showed good cytotoxicity (with IC50 ranging from 0.7483 to 5.572 μg/mL). In general, we observed that the presence of methoxy groups on benzene ring plays an important role in the anticancer activity of this series, especially when they are located in 3,4 (3h) or 3,4,5 (3j) positions. These derivatives could be considered a relevant finding towards the rational design of new leads for antitumoral agents.

  我们合成了一系列多取代的 7-氯-4-喹啉腙衍生物（3a-n），并评估了它们对四种癌细胞株的活性。其中，化合物 3a、3c、3h、3i、3j 和 3n 显示出良好的细胞毒性（IC50 范围为 0.7483 至 5.572 μg/mL）。总的来说，我们观察到苯环上甲氧基的存在对该系列化合物的抗癌活性起着重要作用，尤其是当甲氧基位于 3,4 （3h）或 3,4,5 （3j）位时。这些衍生物可被视为合理设计抗肿瘤药物新线索的一个重要发现。
• 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
• 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.