6-[(2-Bromophenyl)methoxy]-2-chloroquinoline-3-carbaldehyde | 1447374-37-9

• 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: 6-[(2-Bromophenyl)methoxy]-2-chloroquinoline-3-carbaldehyde
• 英文别名: 6-[(2-bromophenyl)methoxy]-2-chloroquinoline-3-carbaldehyde
• CAS: 1447374-37-9
• 化学式: C₁₇H₁₁BrClNO₂
• 分子量: 376.637
• InChiKey: QZOILIPTBMRAHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-[(2-Bromophenyl)methoxy]-2-chloroquinoline-3-carbaldehyde 、 盐酸二甲双胍 在 溶剂黄146 作用下， 以42%的产率得到3-[4-amino-6-(dimethylamino)-2,5-dihydro-1,3,5-triazin-2-yl]-6-[(2-bromobenzyl)oxy]quinolin-2-ol
  参考文献：
  名称：

  带有喹啉部分的二氢三嗪衍生物的合成、抗菌活性和分子对接研究

  摘要：

  在这篇文章中，三个系列的带有喹啉部分的二氢三嗪衍生物（5a、5b、8a-8c 和 9a-9m）已被设计、合成并评估为抗菌剂。发现化合物 8a-8c 是所有测试化合物中最有效的，MIC 值为 1 μg/mL，对几种革兰氏阳性菌（金黄色葡萄球菌 4220 和 MRSA CCARM 3506）和革兰氏阴性菌（大肠杆菌 1924 ) 菌株。此外，3-[4-amino-6-(phenethylamino)-2,5-dihydro-1,3,5-triazin-2-yl)-6-[(3-chlorobenzyl)oxy]quinolin-2-ol (8a) 对铜绿假单胞菌 2742 显示出有效的抑制活性（MIC=2 μg/mL），表明其抗菌谱与阳性对照加替沙星和莫西沙星的抗菌谱相似。构效关系 (SAR) 分析和对接研究表明，二氢三嗪基团与增加喹啉化合物的抗菌效力有关。体外酶研究表明化合物 8a 也显示出 DHFR

  DOI：

  10.1002/cbdv.201900056
• 作为产物：
  描述：

  C₁₆H₁₄BrNO₂ 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 生成 6-[(2-Bromophenyl)methoxy]-2-chloroquinoline-3-carbaldehyde
  参考文献：
  名称：

  Synthesis and biological evaluation of rhodanine derivatives bearing a quinoline moiety as potent antimicrobial agents

  摘要：

  Three series of rhodanine derivatives bearing a quinoline moiety (6a-h, 7a-g, and 8a-e) have been synthesized, characterized, and evaluated as antibacterial agents. The majority of these compounds showed potent antibacterial activities against several different strains of Gram-positive bacteria, including multidrug-resistant clinical isolates. Of the compounds tested, 6g and 8c were identified as the most effective with minimum inhibitory concentration (MIC) values of 1 mu g/mL against multidrug-resistant Gram-positive organisms, including methicillin-resistant and quinolone-resistant Staphylococcus aureus (MRSA and QRSA, respectively). None of the compounds exhibited any activity against the Gram-negative bacteria Escherichia coli 1356 at 64 mu g/mL. The cytotoxic activity assay showed that compounds 6g, 7g and 8e exhibited in vitro antibacterial activity at non-cytotoxic concentrations. Thus, these studies suggest that rhodanine derivatives bearing a quinoline moiety are interesting scaffolds for the development of novel Gram-positive antibacterial agents. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.082

文献信息

• Synthesis and biological evaluation of rhodanine derivatives bearing a quinoline moiety as potent antimicrobial agents
  作者：Meng Guo、Chang-Ji Zheng、Ming-Xia Song、Yan Wu、Liang-Peng Sun、Yin-Jing Li、Yi Liu、Hu-Ri Piao

  DOI：10.1016/j.bmcl.2013.05.082

  日期：2013.8

  Three series of rhodanine derivatives bearing a quinoline moiety (6a-h, 7a-g, and 8a-e) have been synthesized, characterized, and evaluated as antibacterial agents. The majority of these compounds showed potent antibacterial activities against several different strains of Gram-positive bacteria, including multidrug-resistant clinical isolates. Of the compounds tested, 6g and 8c were identified as the most effective with minimum inhibitory concentration (MIC) values of 1 mu g/mL against multidrug-resistant Gram-positive organisms, including methicillin-resistant and quinolone-resistant Staphylococcus aureus (MRSA and QRSA, respectively). None of the compounds exhibited any activity against the Gram-negative bacteria Escherichia coli 1356 at 64 mu g/mL. The cytotoxic activity assay showed that compounds 6g, 7g and 8e exhibited in vitro antibacterial activity at non-cytotoxic concentrations. Thus, these studies suggest that rhodanine derivatives bearing a quinoline moiety are interesting scaffolds for the development of novel Gram-positive antibacterial agents. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis, Antimicrobial Activities, and Molecular Docking Studies of Dihydrotriazine Derivatives Bearing a Quinoline Moiety
  作者：Xueqian Bai、Ying Chen、Zhe Liu、Linhao Zhang、Tianyi Zhang、Bo Feng

  DOI：10.1002/cbdv.201900056

  日期：——

  potent inhibitory activity (MIC=2 μg/mL) against Pseudomonas aeruginosa 2742, indicating that its antibacterial spectrum is similar to those of the positive controls gatifloxacin and moxifloxacin. Structure‐activity relationships (SAR) analyses and docking studies implicated the dihydrotriazine group in increasing the antimicrobial potency of the quinoline compounds. In vitro enzyme study implied that compound

  在这篇文章中，三个系列的带有喹啉部分的二氢三嗪衍生物（5a、5b、8a-8c 和 9a-9m）已被设计、合成并评估为抗菌剂。发现化合物 8a-8c 是所有测试化合物中最有效的，MIC 值为 1 μg/mL，对几种革兰氏阳性菌（金黄色葡萄球菌 4220 和 MRSA CCARM 3506）和革兰氏阴性菌（大肠杆菌 1924 ) 菌株。此外，3-[4-amino-6-(phenethylamino)-2,5-dihydro-1,3,5-triazin-2-yl)-6-[(3-chlorobenzyl)oxy]quinolin-2-ol (8a) 对铜绿假单胞菌 2742 显示出有效的抑制活性（MIC=2 μg/mL），表明其抗菌谱与阳性对照加替沙星和莫西沙星的抗菌谱相似。构效关系 (SAR) 分析和对接研究表明，二氢三嗪基团与增加喹啉化合物的抗菌效力有关。体外酶研究表明化合物 8a 也显示出 DHFR