1-(3-methoxyphenyl)-3-(3-nitrophenyl)urea

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(3-methoxyphenyl)-3-(3-nitrophenyl)urea
• 化学式: C₁₄H₁₃N₃O₄
• 分子量: 287.275
• InChiKey: JKMKYUUDXLRYIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  96.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3-methoxyphenyl)-3-(3-nitrophenyl)urea 在 氢溴酸 、 溶剂黄146 作用下， 以82.8%的产率得到1-(4-hydroxyphenyl)-3-(3-nitrophenyl)urea
  参考文献：
  名称：

  Attenuation of Mycobacterium species through direct and macrophage mediated pathway by unsymmetrical diaryl urea

  摘要：

  Tuberculosis is a major threat for mankind and the emergence of resistance strain of Mycobacterium tuberculosis (Mtb) against first line antibiotics makes it lethal for human civilization. In this study, we have synthesized different diaryl urea derivatives targeting the inhibition of mycolic acid biosynthesis. Among the 39 synthesized molecules, compounds 46, 57, 58 and 86 showed MIC values <= 10 mu g/ml against H37Rv and mc(2)6030 strains. The best molecule with a methyl at ortho position of the first aromatic ring and prenyl group at the meta position of the second aromatic ring showed the MIC value of 5.2 mu g/ml and mu g/ml against H37Rv and mc(2)6030 respectively, with mammalian cytotoxicity of 163.4 mu g/ml. The effective compounds showed selective inhibitory effect on mycolic acid (epoxy mycolate) biosynthesis in C-14-radiolabelled assay. At the same time these molecules also executed their potent immunomodulatory activity by up-regulation of IFN-gamma and IL-12 and down-regulation of IL-10. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.09.083
• 作为产物：
  描述：

  2-硝基苯胺 、 3-甲氧基苯异氰酸 以 二氯甲烷 为溶剂， 以65.2%的产率得到1-(3-methoxyphenyl)-3-(3-nitrophenyl)urea
  参考文献：
  名称：

  Attenuation of Mycobacterium species through direct and macrophage mediated pathway by unsymmetrical diaryl urea

  摘要：

  Tuberculosis is a major threat for mankind and the emergence of resistance strain of Mycobacterium tuberculosis (Mtb) against first line antibiotics makes it lethal for human civilization. In this study, we have synthesized different diaryl urea derivatives targeting the inhibition of mycolic acid biosynthesis. Among the 39 synthesized molecules, compounds 46, 57, 58 and 86 showed MIC values <= 10 mu g/ml against H37Rv and mc(2)6030 strains. The best molecule with a methyl at ortho position of the first aromatic ring and prenyl group at the meta position of the second aromatic ring showed the MIC value of 5.2 mu g/ml and mu g/ml against H37Rv and mc(2)6030 respectively, with mammalian cytotoxicity of 163.4 mu g/ml. The effective compounds showed selective inhibitory effect on mycolic acid (epoxy mycolate) biosynthesis in C-14-radiolabelled assay. At the same time these molecules also executed their potent immunomodulatory activity by up-regulation of IFN-gamma and IL-12 and down-regulation of IL-10. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.09.083

文献信息

• Über den Umsatz aromatischer Isocyansäure-ester mit aromatischen Aminen
  作者：C. Naegeli、A. Tyabji、L. Conrad

  DOI：10.1002/hlca.193802101140

  日期：——

  1. Wenn aromatische Isocyansäure-ester mit aromatischen Aminen in aromatischen Kohlenwasserstoffen sich miteinander umsetzen, so ordnen sich die Substituenten bezüglich ihres Einflusses auf die Aktivität der Isocyansäure-Gruppe in die Reihe

  1.当芳族异氰酸酯与芳烃中的芳族胺反应时，取代基将根据其对异氰酸酯基活性的影响进行排序
• Über die Einwirkung von Wasser auf aromatische lsocyansäure-ester
  作者：C. Naegeli、A. Tyabji、L. Conrad、F. Litwan

  DOI：10.1002/hlca.193802101139

  日期：——

  1. Die Reaktionswege, die bei Umsatz aromatischer Isocyansäure-ester mit Wasser zum zugehörigen Diarylharnstoff bzw. zum entsprechenden Arylamin führen, wurden systematisch untersucht: (a) durch den Umsatz der Isocyanate mit Wasser unter verschiedenartigen Bedingungen; (b) durch den Umsatz mit Arylaminen in Benzol-Toluol-Lösung; (c) durch den gleichzeitigen Umsatz mit Wasser und Arylamin in Aceton;

  1.已经系统地研究了使芳族异氰酸酯与水反应时导致缔合的二芳基脲或相应的芳基胺的反应途径：（a）通过在不同条件下使异氰酸酯与水反应；（b）通过与芳胺在苯-甲苯溶液中的转化；（c）与水和芳基胺在丙酮中同时反应；（d）通过转换获得2％的收益。钾碱液和不同浓度的盐酸；（e）通过用甲醇转化。实验结果为z。部分内容在表1（p。1102）中，然后用文字简要概述。参考了实验的制备重要性（第1101、1118和1125页）。
• Ein modifizierter<i>Curtius</i>'scher Abbau VII. Der Abbau der aromatischen Säuren
  作者：C. Naegeli、A. Tyabji

  DOI：10.1002/hlca.19330160153

  日期：——
• Attenuation of Mycobacterium species through direct and macrophage mediated pathway by unsymmetrical diaryl urea
  作者：Anand Babu Velappan、Mamilla R. Charan Raja、Dhrubajyoti Datta、Yi Ting Tsai、Iman Halloum、Baojie Wan、Laurent Kremer、Hugo Gramajo、Scott G. Franzblau、Santanu Kar Mahapatra、Joy Debnath

  DOI：10.1016/j.ejmech.2016.09.083

  日期：2017.1

  Tuberculosis is a major threat for mankind and the emergence of resistance strain of Mycobacterium tuberculosis (Mtb) against first line antibiotics makes it lethal for human civilization. In this study, we have synthesized different diaryl urea derivatives targeting the inhibition of mycolic acid biosynthesis. Among the 39 synthesized molecules, compounds 46, 57, 58 and 86 showed MIC values <= 10 mu g/ml against H37Rv and mc(2)6030 strains. The best molecule with a methyl at ortho position of the first aromatic ring and prenyl group at the meta position of the second aromatic ring showed the MIC value of 5.2 mu g/ml and mu g/ml against H37Rv and mc(2)6030 respectively, with mammalian cytotoxicity of 163.4 mu g/ml. The effective compounds showed selective inhibitory effect on mycolic acid (epoxy mycolate) biosynthesis in C-14-radiolabelled assay. At the same time these molecules also executed their potent immunomodulatory activity by up-regulation of IFN-gamma and IL-12 and down-regulation of IL-10. (C) 2016 Elsevier Masson SAS. All rights reserved.