3,7-dimethylquinoxaline-2-carboxylic acid p-methylbenzylamide 1,4-di-N-oxide | 1253059-06-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3,7-dimethylquinoxaline-2-carboxylic acid p-methylbenzylamide 1,4-di-N-oxide
• 英文别名: 3,7-dimethyl-1,4-dioxido-N-(p-tolylmethyl)quinoxaline-1,4-diium-2-carboxamide；3,7-dimethyl-N-[(4-methylphenyl)methyl]-4-oxido-1-oxoquinoxalin-1-ium-2-carboxamide
• CAS: 1253059-06-1
• 化学式: C₁₉H₁₉N₃O₃
• 分子量: 337.378
• InChiKey: LFJPVEWCRMQDHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  75.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-甲基-2-硝基苯胺 在 sodium hypochlorite 、 C.I.酸性橙108 、 calcium chloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 3,7-dimethylquinoxaline-2-carboxylic acid p-methylbenzylamide 1,4-di-N-oxide
  参考文献：
  名称：

  Studies on Log Po/w of Quinoxaline di-N-Oxides: A Comparison of RP-HPLC Experimental and Predictive Approaches

  摘要：

  根据我们之前的论文，合成了一系列喹喔啉-2-羧酰胺1,4-二-N-氧化物衍生物，并研究其作为抗结核药物的潜力。在这里，我们研究了摇瓶法的能力，并通过反相高效液相色谱（RP-HPLC）分析确定了20种化合物的保留时间（以log K表示）。我们发现，RP-HPLC分析对log P的预测可以达到较高的准确性，可以替代摇瓶法，避免了喹喔啉二-N-氧化物所带来的实验问题。研究的化合物被提交至ALOGPS模块，以比较实验得到的log Po/w值和预测数据。此外，我们还进行了QSAR关系的初步体外筛选，确认了还原峰电位、脂溶性、氢键供体能力和分子尺寸描述符对抗结核活性的影响。

  DOI：

  10.3390/molecules16097893

文献信息

• Synthesis and antimycobacterial activity of new quinoxaline-2-carboxamide 1,4-di-N-oxide derivatives
  作者：Elsa Moreno、Saioa Ancizu、Silvia Pérez-Silanes、Enrique Torres、Ignacio Aldana、Antonio Monge

  DOI：10.1016/j.ejmech.2010.06.036

  日期：2010.10

  As a continuation of our research and with the aim of obtaining new anti-tuberculosis agents which can improve the current chemotherapeutic anti-tuberculosis treatments, forty-three new quinoxaline-2-carboxamide 1,4-di-N-oxide derivatives were synthesized and evaluated for in vitro anti-tuberculosis activity against Mycobacterium tuberculosis strain H(37)Rv. Active compounds were also screened to assess toxicity to a VERO cell line. Results indicate that compounds with a methyl moiety substituted in position 3 and unsubstituted benzyl substituted on the carboxamide group provide an efficient approach for further development of anti-tuberculosis agents. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Studies on Log Po/w of Quinoxaline di-N-Oxides: A Comparison of RP-HPLC Experimental and Predictive Approaches
  作者：Elsa Moreno、Elisabetta Gabano、Enrique Torres、James A. Platts、Mauro Ravera、Ignacio Aldana、Antonio Monge、Silvia Pérez-Silanes

  DOI：10.3390/molecules16097893

  日期：——

  As reported in our previous papers, a series of quinoxaline-2-carboxamide 1,4-di-N-oxide derivatives were synthesized and studied as anti-tuberculosis agents. Here, the capability of the shake-flask method was studied and the retention time (expressed as log K) of 20 compounds were determined by RP-HPLC analysis. We found that the prediction of log P by the RP-HPLC analysis can result in a high accuracy and can replace the shake-flask method avoiding the experimental problems presented by quinoxaline di-N-oxides. The studied compounds were subjected to the ALOGPS module with the aim of comparing experimental log Po/w values and predicted data. Moreover, a preliminary in silico screening of the QSAR relationship was made confirming the influence of reduction peak potential, lipophilicity, H-bond donor capacity and molecular dimension descriptors on anti-tuberculosis activity.

  根据我们之前的论文，合成了一系列喹喔啉-2-羧酰胺1,4-二-N-氧化物衍生物，并研究其作为抗结核药物的潜力。在这里，我们研究了摇瓶法的能力，并通过反相高效液相色谱（RP-HPLC）分析确定了20种化合物的保留时间（以log K表示）。我们发现，RP-HPLC分析对log P的预测可以达到较高的准确性，可以替代摇瓶法，避免了喹喔啉二-N-氧化物所带来的实验问题。研究的化合物被提交至ALOGPS模块，以比较实验得到的log Po/w值和预测数据。此外，我们还进行了QSAR关系的初步体外筛选，确认了还原峰电位、脂溶性、氢键供体能力和分子尺寸描述符对抗结核活性的影响。