6-cyclohexylbenzo[b]phenanthridine-5,7,12(6H)-trione | 1610421-12-9

• 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-cyclohexylbenzo[b]phenanthridine-5,7,12(6H)-trione
• 英文别名: 6-Cyclohexylbenzo[b]phenanthridine-5,7,12-trione；6-cyclohexylbenzo[b]phenanthridine-5,7,12-trione
• CAS: 1610421-12-9
• 化学式: C₂₃H₁₉NO₃
• 分子量: 357.409
• InChiKey: DXSKMEUDLZBFNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(2-溴苯基)-1,3-二恶烷 在 copper(l) iodide 、 四(三苯基膦)钯 、 正丁基锂 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 23.0h， 生成 6-cyclohexylbenzo[b]phenanthridine-5,7,12(6H)-trione
  参考文献：
  名称：

  Bioreductively Activated Reactive Oxygen Species (ROS) Generators as MRSA Inhibitors

  摘要：

  The number of cases of drug resistant Staphylococcus aureus infections is on the rise globally and new strategies to identify drug candidates with novel mechanisms of action are in urgent need. Here, we report the synthesis and evaluation of a series of benzo[b]phenanthridine-S,7,12(6H)-triones, which were designed based on redox-active natural products. We find that the in vitro inhibitory activity of 6-(prop-2-ynyl)benzo[b]phenanthridine-5,7,12(6H)-trione (If) against methicillin-resistant Staphylococcus aureus (MRSA), including a panel of patient-derived strains, is comparable or better than vancomycin. We show that the lead compound generates reactive oxygen species (ROS) in the cell, contributing to its antibacterial activity.

  DOI：

  10.1021/ml5001118

文献信息

• Bioreductively Activated Reactive Oxygen Species (ROS) Generators as MRSA Inhibitors
  作者：Vinayak S. Khodade、Mallojjala Sharath Chandra、Ankita Banerjee、Surobhi Lahiri、Mallikarjuna Pulipeta、Radha Rangarajan、Harinath Chakrapani

  DOI：10.1021/ml5001118

  日期：2014.7.10

  The number of cases of drug resistant Staphylococcus aureus infections is on the rise globally and new strategies to identify drug candidates with novel mechanisms of action are in urgent need. Here, we report the synthesis and evaluation of a series of benzo[b]phenanthridine-S,7,12(6H)-triones, which were designed based on redox-active natural products. We find that the in vitro inhibitory activity of 6-(prop-2-ynyl)benzo[b]phenanthridine-5,7,12(6H)-trione (If) against methicillin-resistant Staphylococcus aureus (MRSA), including a panel of patient-derived strains, is comparable or better than vancomycin. We show that the lead compound generates reactive oxygen species (ROS) in the cell, contributing to its antibacterial activity.