1-(4-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-(4-methoxyphenyl)-3-(3-nitrophenyl)urea
• 英文别名: N-(4-methoxy-phenyl)-N'-(3-nitro-phenyl)-urea；N-(4-Methoxy-phenyl)-N'-(3-nitro-phenyl)-harnstoff
• 化学式: C₁₄H₁₃N₃O₄
• 分子量: 287.275
• InChiKey: ZXZGOGLXDKDRHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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-(4-methoxyphenyl)-3-(3-nitrophenyl)urea 在 氢溴酸 、 溶剂黄146 作用下， 以78.3%的产率得到1-(3-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：

  4-methoxy-N'-(3-nitrophenyl)benzohydrazide 以30%的产率得到
  参考文献：
  名称：

  FAHMY A. F. M.; ALY N. F.; ELKOMY M. A., INDIAN J. CHEM., 1979, B16, NO 11, 997-999

  摘要：

  DOI：

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
• Sah, Journal of the Chinese Chemical Society (Peking), 1946, vol. 13, p. 22,26,27
  作者：Sah

  DOI：——

  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.
• FAHMY A. F. M.; ALY N. F.; ELKOMY M. A., INDIAN J. CHEM., 1979, B16, NO 11, 997-999
  作者：FAHMY A. F. M.、 ALY N. F.、 ELKOMY M. A.

  DOI：——

  日期：——