3-chlorophenylquinolin-3-yl-amine | 1021328-14-2

• 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: 3-chlorophenylquinolin-3-yl-amine
• 英文别名: N-(3-chlorophenyl)quinolin-3-amine
• CAS: 1021328-14-2
• 化学式: C₁₅H₁₁ClN₂
• 分子量: 254.719
• InChiKey: SEYKAKCMCZQJFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 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：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-chlorophenylquinolin-3-yl-amine 在 palladium diacetate 、 三氟乙酸 、 氨 、 水 作用下， 反应 6.0h， 生成 6-chloroindolo[3,2-b]quinoline
  参考文献：
  名称：

  Identification of 3-phenylaminoquinolinium and 3-phenylaminopyridinium salts as new agents against opportunistic fungal pathogens

  摘要：

  Previous studies on the indoloquinoline alkaloid, cryptolepine (2), revealed that it has antii-nfective properties among other activities. Using Structure-activity relationship (SAR) techniques, several ring-opened analogs of cryptolepine (3-phenylaminopyridinium and 3-phenylaminoquinolinium derivatives) were designed to improve the potency and lower the cytotoxicity shown by several of the precursor agents. Results indicate that these ring-opened analogs constitute new anti-infective agents with over a 100-fold potency and several fold lower cytotoxicity than cryptolepine from which they are derived. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2010.10.065
• 作为产物：
  描述：

  喹啉 在 叔丁基过氧化氢 、 碘 、 palladium diacetate 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 12.0h， 生成 3-chlorophenylquinolin-3-yl-amine
  参考文献：
  名称：

  Structural Simplification of Cryptolepine to Obtain Novel Antifungal Quinoline Derivatives against Phytopathogenic Fungi

  摘要：

  DOI：

  10.1021/acs.jafc.2c07575

文献信息

• [EN] DIARYLAMINE-SUBSTITUTED QUINOLONES USEFUL AS INDUCIBLE NITRIC OXIDE SYNTHASE INHIBITORS<br/>[FR] QUINOLONES SUBSTITUÉES PAR DIARYLAMINE UTILES COMME INHIBITEURS DE L'OXYDE NITRIQUE SYNTHASE INDUCTIBLE.
  申请人：KALYPSYS INC

  公开号：WO2009029617A1

  公开（公告）日：2009-03-05

  Novel diarylamine-substituted quinolone compounds and pharmaceutical compositions, certain of which have been found to inhibit inducible NOS synthase have been discovered, together with methods of synthesizing and using the compounds including methods for the treatment of iNOS-mediated diseases in a patient by administering the compounds.

  已发现新的含有二芳胺基取代喹诺酮化合物和药物组合物，其中一些已被发现能抑制诱导型NOS合成酶，还包括合成和使用这些化合物的方法，包括通过给患者施用这些化合物治疗iNOS介导的疾病的方法。
• A short and convenient synthesis and evaluation of the antiinfective properties of indoloquinoline alkaloids: 10 <i>H</i> ‐Indolo[3,2‐ <i>b</i> ]quinoline and 7 <i>H</i> ‐indolo[2,3‐ <i>c</i> ]quinolines
  作者：Jagan R. Etukala、E. V. K. Suresh Kumar、Seth Y. Ablordeppey

  DOI：10.1002/jhet.5570450232

  日期：2008.3

  10H-Indolo[3,2-b]quinoline and 7H-indolo[2,3-c]quinoline have been synthesized in two steps using a modified approach to our previous reported method. Starting from commercially available 3-aminoquinoline and phenylboronic acid, the first step involved a copper acetate-catalyzed coupling reaction and the second utilized a palladium acetate-catalyzed intramolecular arylation reaction in the presence

  10 H-吲哚并[3,2- b ]喹啉和7H-吲哚并[2,3- c ]喹啉已使用我们先前报道的方法的改进方法分两步合成。从可商购的3-氨基喹啉和苯基硼酸开始，第一步涉及乙酸铜催化的偶联反应，第二步在三氟乙酸作为溶剂存在下利用乙酸钯催化的分子内芳基化反应。还评估了选定数量的化合物的抗感染活性。
• Identification of 3-phenylaminoquinolinium and 3-phenylaminopyridinium salts as new agents against opportunistic fungal pathogens
  作者：Tryphon K. Mazu、Jagan R. Etukala、Xue Y. Zhu、Melissa R. Jacob、Shabana I. Khan、Larry A. Walker、Seth Y. Ablordeppey

  DOI：10.1016/j.bmc.2010.10.065

  日期：2011.1

  Previous studies on the indoloquinoline alkaloid, cryptolepine (2), revealed that it has antii-nfective properties among other activities. Using Structure-activity relationship (SAR) techniques, several ring-opened analogs of cryptolepine (3-phenylaminopyridinium and 3-phenylaminoquinolinium derivatives) were designed to improve the potency and lower the cytotoxicity shown by several of the precursor agents. Results indicate that these ring-opened analogs constitute new anti-infective agents with over a 100-fold potency and several fold lower cytotoxicity than cryptolepine from which they are derived. Published by Elsevier Ltd.
• Structural Simplification of Cryptolepine to Obtain Novel Antifungal Quinoline Derivatives against Phytopathogenic Fungi
  作者：Hai-Xin Li、Xiong-Fei Luo、Peng Deng、Shao-Yong Zhang、Han Zhou、Yan Yan Ding、Yi-Rong Wang、Ying-Qian Liu、Zhi-Jun Zhang

  DOI：10.1021/acs.jafc.2c07575

  日期：2023.2.8