7-chloro-N-(thiophen-2-ylmethylideneamino)quinolin-4-amine | 391616-92-5

• 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-N-(thiophen-2-ylmethylideneamino)quinolin-4-amine
• CAS: 391616-92-5
• 化学式: C₁₄H₁₀ClN₃S
• 分子量: 287.773
• InChiKey: FCVCFHUYRQGYGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 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：
  65.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-chloro-N-(thiophen-2-ylmethylideneamino)quinolin-4-amine 、 氯乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 3-Chloro-1-[(7-chloroquinolin-4-yl)amino]-4-thiophen-2-ylazetidin-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-N-(thiophen-2-ylmethylideneamino)quinolin-4-amine
  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

• 1-(7-Chloroquinolin-4-yl)-2-[(1H-pyrrol-2-yl)methylene]hydrazine: a potent compound against cancer
  作者：Raquel Carvalho Montenegro、Letícia Veras Lotufo、Manoel Odorico de Moraes、Cláudia do Ó. Pessoa、Felipe Augusto Rocha Rodrigues、Marcelle de Lima Ferreira Bispo、Camila Cataldi de Alcantara、Carlos Roland Kaiser、Marcus Vinícius Nora de Souza

  DOI：10.1007/s00044-011-9894-8

  日期：2012.11

  Heteroaromatic derivatives (3a-f) have been synthesized and evaluated for their activity against four cancer cell lines. Among the studied compounds, 1-(7-Chloroquinolin-4-yl)-2-[(1H-pyrrol-2-yl)methylene]hydrazine (3e) exhibited an excellent cytotoxic activity against the referred lines, and especially on melanoma cells (MDAMB-435). In this case, compound 3e is four times more active than the standard substance Doxorubicin. Together with other results from our group, 7-chloro-4-quinolinylhydrazones derived from chloroquine could be considered a relevant finding toward the rational design of new leads for antitumor compounds.
• 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.