7-chloro-4-[(3-hydroxyphenyl)amino]quinolinium chloride | 154179-39-2

• 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-hydroxyphenyl)amino]quinolinium chloride
• 英文别名: 3-[(7-Chloroquinolin-4-yl)amino]phenol hydrochloride；3-[(7-chloroquinolin-4-yl)amino]phenol;hydrochloride
• CAS: 154179-39-2
• 化学式: C₁₅H₁₁ClN₂O*ClH
• 分子量: 307.179
• InChiKey: CFDLXKULBJIEBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.2
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 7-chloro-4-[(3-hydroxyphenyl)amino]quinolinium chloride 、 叔丁胺 以 仲丁醇 为溶剂， 生成 3-(tert-butyl)-N-(7-chloroquinolin-4-yl)-3,4-dihydro-2H-benzo[e][1,3]oxazin-7-amine
  参考文献：
  名称：

  Candidate Selection and Preclinical Evaluation of N-tert-Butyl Isoquine (GSK369796), An Affordable and Effective 4-Aminoquinoline Antimalarial for the 21st Century

  摘要：

  N-tert-Butyl isoquine (4) (GSK369796) is a 4-aminoquinoline drug candidate selected and developed as part of a public-private partnership between academics at Liverpool, MMV, and GSK pharmaceuticals. This molecule was rationally designed based on chemical, toxicological, pharmacokinetic, and pharmacodynamic considerations and was selected based on excellent activity against Plasmodium falciparum in vitro and rodent malaria parasites in vivo. The optimized chemistry delivered this novel synthetic quinoline in a two-step procedure from cheap and readily available starting materials. The molecule has a full industry standard preclinical development program allowing first into humans to proceed. Employing chloroquine (1) and amodiaquine (2) as comparator molecules in the preclinical plan, the first preclinical dossier of pharmacokinetic, toxicity, and safety pharmacology has also been established for the 4-aminoquinoline antimalarial class. These studies have revealed preclinical liabilities that have never translated into the human experience. This has resulted in the availability of critical information to other drug development teams interested in developing antimalarials within this class.

  DOI：

  10.1021/jm8012618
• 作为产物：
  描述：

  4,7-二氯喹啉 、 3-氨基苯酚 以 乙醇 为溶剂， 以95%的产率得到7-chloro-4-[(3-hydroxyphenyl)amino]quinolinium chloride
  参考文献：
  名称：

  环取代的 4-芳基氨基-7-氯喹啉氯化物的抗分枝杆菌和光合电子传递抑制活性。

  摘要：

  在本研究中，制备并表征了一系列二十五个环取代的 4-芳基氨基-7-氯喹啉氯化物。测试了这些化合物与抑制菠菜 (Spinacia oleracea L.) 叶绿体中光合电子传递 (PET) 相关的活性，并且还针对分枝杆菌物种对合成的化合物进行了初步体外筛选。4-[(2-Bromophenyl)amino]-7-chloroquinolinium chloride 对 M. marinum、M. kansasii、M. smegmatis 和 7-chloro-4-[(2-methylphenyl)amino]quinolinium chloride 显示出高生物活性对耻垢分枝杆菌和鸟分枝杆菌亚种的生物活性。副结核病。最有效的化合物表现出相当低的毒性（LD₅₀ > 20 μmol/L) 在初步体外细胞毒性筛选中针对人单核细胞白血病 THP-1 细胞系。发现测试的化合物在光系统 II 中抑制 P

  DOI：

  10.3390/molecules180910648

文献信息

• Barlin, Gordon B.; Ireland, Stephen J.; Nguyen, Trang M. T., Australian Journal of Chemistry, 1993, vol. 46, # 11, p. 1685 - 1694
  作者：Barlin, Gordon B.、Ireland, Stephen J.、Nguyen, Trang M. T.、Kotecka, Barbara、Rieckmann, Karl H.

  DOI：——

  日期：——
• Antimycobacterial and Photosynthetic Electron Transport Inhibiting Activity of Ring-Substituted 4-Arylamino-7-Chloroquinolinium Chlorides
  作者：Jan Otevrel、Pavel Bobal、Iveta Zadrazilova、Rodney Govender、Matus Pesko、Stanislava Keltosova、Petra Koleckarova、Petr Marsalek、Ales Imramovsky、Aidan Coffey、Jim O'Mahony、Peter Kollar、Alois Cizek、Katarina Kralova、Josef Jampilek

  DOI：10.3390/molecules180910648

  日期：——

  In this study, a series of twenty-five ring-substituted 4-arylamino-7-chloroquinolinium chlorides were prepared and characterized. The compounds were tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts and also primary in vitro screening of the synthesized compounds was performed against mycobacterial species. 4-

  在本研究中，制备并表征了一系列二十五个环取代的 4-芳基氨基-7-氯喹啉氯化物。测试了这些化合物与抑制菠菜 (Spinacia oleracea L.) 叶绿体中光合电子传递 (PET) 相关的活性，并且还针对分枝杆菌物种对合成的化合物进行了初步体外筛选。4-[(2-Bromophenyl)amino]-7-chloroquinolinium chloride 对 M. marinum、M. kansasii、M. smegmatis 和 7-chloro-4-[(2-methylphenyl)amino]quinolinium chloride 显示出高生物活性对耻垢分枝杆菌和鸟分枝杆菌亚种的生物活性。副结核病。最有效的化合物表现出相当低的毒性（LD₅₀ > 20 μmol/L) 在初步体外细胞毒性筛选中针对人单核细胞白血病 THP-1 细胞系。发现测试的化合物在光系统 II 中抑制 P
• Candidate Selection and Preclinical Evaluation of <i>N</i>-<i>tert</i>-Butyl Isoquine (GSK369796), An Affordable and Effective 4-Aminoquinoline Antimalarial for the 21st Century
  作者：Paul M. O’Neill、B. Kevin Park、Alison E. Shone、James L. Maggs、Phillip Roberts、Paul A. Stocks、Giancarlo A. Biagini、Patrick G. Bray、Peter Gibbons、Neil Berry、Peter A. Winstanley、Amira Mukhtar、Richard Bonar-Law、Stephen Hindley、Ramesh B. Bambal、Charles B. Davis、Martin Bates、Timothy K. Hart、Stephanie L. Gresham、Ron M. Lawrence、Richard A. Brigandi、Federico M. Gomez-delas-Heras、Domingo V. Gargallo、Stephen A. Ward

  DOI：10.1021/jm8012618

  日期：2009.3.12

  N-tert-Butyl isoquine (4) (GSK369796) is a 4-aminoquinoline drug candidate selected and developed as part of a public-private partnership between academics at Liverpool, MMV, and GSK pharmaceuticals. This molecule was rationally designed based on chemical, toxicological, pharmacokinetic, and pharmacodynamic considerations and was selected based on excellent activity against Plasmodium falciparum in vitro and rodent malaria parasites in vivo. The optimized chemistry delivered this novel synthetic quinoline in a two-step procedure from cheap and readily available starting materials. The molecule has a full industry standard preclinical development program allowing first into humans to proceed. Employing chloroquine (1) and amodiaquine (2) as comparator molecules in the preclinical plan, the first preclinical dossier of pharmacokinetic, toxicity, and safety pharmacology has also been established for the 4-aminoquinoline antimalarial class. These studies have revealed preclinical liabilities that have never translated into the human experience. This has resulted in the availability of critical information to other drug development teams interested in developing antimalarials within this class.