2-Methoxy-5-methylphenanthridin-5-ium;chloride | 1421005-53-9

• 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: 2-Methoxy-5-methylphenanthridin-5-ium;chloride
• 英文别名: 2-methoxy-5-methylphenanthridin-5-ium;chloride
• CAS: 1421005-53-9
• 化学式: C₁₅H₁₄NO*Cl
• 分子量: 259.735
• InChiKey: KFEPFSNOLGZHBN-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.17
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-methoxy-5-methylphenanthridin-6(5H)-one 在 二异丁基氢化铝 、 盐酸 作用下， 以 四氢呋喃 、 乙基苯 、 水 为溶剂， 反应 1.0h， 以29%的产率得到2-Methoxy-5-methylphenanthridin-5-ium;chloride
  参考文献：
  名称：

  FtsZ抑制剂5-甲基菲啶鎓衍生物的合成及抑菌活性

  摘要：

  设计，合成和评估了5-甲基菲啶鎓衍生物对各种革兰氏阳性和阴性细菌的体外抗菌活性和细胞分裂抑制活性。其中化合物5A2，5B1，5B2，5B3，5C1和5C2显示在目标的最佳的抗菌活性用4微克/毫升的抗的MIC值枯草芽孢杆菌ATCC9372和化脓性链球菌PS，显示出比Sanguinarine更好的2倍的活性。SARs表明，在2-位具有烷基侧链的5-甲基菲啶鎓衍生物，尤其是直链烷基侧链发挥了更好的针对目标的抗菌活性。

  DOI：

  10.1016/j.bmcl.2017.06.005

文献信息

• Synthesis, topoisomerase-targeting activity and growth inhibition of lycobetaine analogs
  作者：Simone A. Baechler、Markus Fehr、Michael Habermeyer、Andreas Hofmann、Karl-Heinz Merz、Heinz-Herbert Fiebig、Doris Marko、Gerhard Eisenbrand

  DOI：10.1016/j.bmc.2012.11.011

  日期：2013.2

  The plant alkaloid lycobetaine has potent topoisomerase-targeting properties and shows anticancer activity. Based on these findings, several lycobetaine analogs were synthesized mainly differing in their substituents at 2, 8 and 9 position and their biological activities were evaluated. The topoisomerase-targeting properties and cytotoxicity of these structural analogs were assessed in the human gastric carcinoma cell line GXF251L. Performing a plasmid relaxation assay, an increased inhibition of topoisomerase I was found with N-methylphenanthridinium chlorides bearing a 8,9-methylenedioxy moiety or a methoxy group in 2-position. Furthermore, quaternized phenanthridinium derivatives bearing either a 2-methoxy or a 8,9-methylenedioxy moiety in conjunction with a 2-hydroxy or 2-methoxy group display potent topoisomerase II inhibition as shown by decatenation of kinetoplast DNA. In general, the N-methylphenanthridinium chlorides possess more potency in inhibiting topoisomerase I than topoisomerase II. All quaternized derivatives also exhibited potent inhibition of tumor cell growth in the low micromolar concentration range. Hence, N-methylphenanthridinium compounds were found to represent a promising class of compounds, potently inhibiting both, topoisomerases I and II, and may be further developed into clinically useful topoisomerase inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis and antibacterial activity of 5-methylphenanthridium derivatives as FtsZ inhibitors
  作者：Fang Liu、Henrietta Venter、Fangchao Bi、Susan J. Semple、Jingru Liu、Chaobin Jin、Shutao Ma

  DOI：10.1016/j.bmcl.2017.06.005

  日期：2017.8

  5-Methylphenanthridium derivatives were designed, synthesized and evaluated for their in vitro antibacterial activity and cell division inhibitory activity against various Gram-positive and -negative bacteria. Among them, compounds 5A2, 5B1, 5B2, 5B3, 5C1 and 5C2 displayed the best on-target antibacterial activity with an MIC value of 4 µg/mL against B. subtilis ATCC9372 and S. pyogenes PS, showing

  设计，合成和评估了5-甲基菲啶鎓衍生物对各种革兰氏阳性和阴性细菌的体外抗菌活性和细胞分裂抑制活性。其中化合物5A2，5B1，5B2，5B3，5C1和5C2显示在目标的最佳的抗菌活性用4微克/毫升的抗的MIC值枯草芽孢杆菌ATCC9372和化脓性链球菌PS，显示出比Sanguinarine更好的2倍的活性。SARs表明，在2-位具有烷基侧链的5-甲基菲啶鎓衍生物，尤其是直链烷基侧链发挥了更好的针对目标的抗菌活性。